chore: release v0.21.0 (#1472 )

Co-authored-by: ironclaw-ci[bot] <266877842+ironclaw-ci[bot]@users.noreply.github.com>
Merge pull request #1420 from nearai/staging-promote/71f9012d-23307625134
2026-08-28 00:20:16 +00:00 · 2026-03-20 11:23:39 -07:00 · 2026-03-20 10:51:43 -07:00 · 2026-03-20 10:33:57 -07:00 · 2026-03-20 10:11:43 -07:00 · 2026-03-20 10:11:32 -07:00
214 changed files with 22634 additions and 9486 deletions
@@ -18,6 +18,11 @@ DATABASE_POOL_SIZE=10

 # === OpenAI Direct ===
 # OPENAI_API_KEY=sk-...
+# Reuse Codex CLI auth.json instead of setting OPENAI_API_KEY manually.
+# Works with both OpenAI API-key mode and Codex ChatGPT OAuth mode.
+# In ChatGPT mode this uses the private `chatgpt.com/backend-api/codex` endpoint.
+# LLM_USE_CODEX_AUTH=true
+# CODEX_AUTH_PATH=~/.codex/auth.json

 # === NEAR AI (Chat Completions API) ===
 # Two auth modes:
@@ -73,7 +78,7 @@ NEARAI_AUTH_URL=https://private.near.ai
 # === MiniMax ===
 # LLM_BACKEND=minimax
 # MINIMAX_API_KEY=...
-# MINIMAX_MODEL=MiniMax-M2.5
+# MINIMAX_MODEL=MiniMax-M2.7
 # MINIMAX_BASE_URL=https://api.minimax.io/v1   # default (global); use https://api.minimaxi.com/v1 for China

 # === Anthropic Direct ===
@@ -174,7 +174,7 @@ jobs:

      - name: Run E2E tests
        run: |
-          pytest tests/e2e/ -v -x --timeout=120
+          pytest tests/e2e/ -v --timeout=120
        env:
          RUST_LOG: ironclaw=info
          RUST_BACKTRACE: "1"
@@ -5,6 +5,8 @@ on:
    - cron: "0 6 * * 1"  # Weekly Monday 6 AM UTC
  workflow_dispatch:
  pull_request:
+    branches:
+      - main
    paths:
      - "src/channels/web/**"
      - "tests/e2e/**"
@@ -50,9 +52,11 @@ jobs:
          - group: core
            files: "tests/e2e/scenarios/test_connection.py tests/e2e/scenarios/test_chat.py tests/e2e/scenarios/test_sse_reconnect.py tests/e2e/scenarios/test_html_injection.py tests/e2e/scenarios/test_csp.py"
          - group: features
-            files: "tests/e2e/scenarios/test_skills.py tests/e2e/scenarios/test_tool_approval.py"
+            files: "tests/e2e/scenarios/test_skills.py tests/e2e/scenarios/test_tool_approval.py tests/e2e/scenarios/test_webhook.py"
          - group: extensions
-            files: "tests/e2e/scenarios/test_extensions.py tests/e2e/scenarios/test_extension_oauth.py tests/e2e/scenarios/test_wasm_lifecycle.py tests/e2e/scenarios/test_tool_execution.py tests/e2e/scenarios/test_pairing.py tests/e2e/scenarios/test_oauth_credential_fallback.py tests/e2e/scenarios/test_routine_oauth_credential_injection.py"
+            files: "tests/e2e/scenarios/test_extensions.py tests/e2e/scenarios/test_extension_oauth.py tests/e2e/scenarios/test_telegram_token_validation.py tests/e2e/scenarios/test_telegram_hot_activation.py tests/e2e/scenarios/test_wasm_lifecycle.py tests/e2e/scenarios/test_tool_execution.py tests/e2e/scenarios/test_pairing.py tests/e2e/scenarios/test_mcp_auth_flow.py tests/e2e/scenarios/test_oauth_credential_fallback.py tests/e2e/scenarios/test_routine_oauth_credential_injection.py"
+          - group: routines
+            files: "tests/e2e/scenarios/test_owner_scope.py tests/e2e/scenarios/test_routine_event_batch.py"
    steps:
      - uses: actions/checkout@v6

@@ -43,12 +43,42 @@ jobs:
            fi
          fi

-          if [ "$IS_FIX" = false ]; then
-            echo "Not a fix PR — skipping regression test check."
+          # --- 1b. Does this PR touch high-risk state machine or resilience code? ---
+          CHANGED_FILES=$(git diff --name-only "${BASE_REF}...${HEAD_REF}")
+
+          TOUCHES_HIGH_RISK=false
+          HIGH_RISK_PATTERNS=(
+            "src/context/state.rs"
+            "src/agent/session.rs"
+            "src/llm/circuit_breaker.rs"
+            "src/llm/retry.rs"
+            "src/llm/failover.rs"
+            "src/agent/self_repair.rs"
+            "src/agent/agentic_loop.rs"
+            "src/tools/execute.rs"
+            "crates/ironclaw_safety/src/"
+          )
+
+          for pattern in "${HIGH_RISK_PATTERNS[@]}"; do
+            if echo "$CHANGED_FILES" | grep -q "$pattern"; then
+              TOUCHES_HIGH_RISK=true
+              echo "High-risk file matched: $pattern"
+              break
+            fi
+          done
+
+          # Skip only if NEITHER condition holds — no double-firing on fix PRs
+          if [ "$IS_FIX" = false ] && [ "$TOUCHES_HIGH_RISK" = false ]; then
+            echo "Not a fix PR and no high-risk files changed — skipping."
            exit 0
          fi

-          echo "Fix PR detected."
+          if [ "$IS_FIX" = true ]; then
+            echo "Fix PR detected."
+          fi
+          if [ "$TOUCHES_HIGH_RISK" = true ]; then
+            echo "High-risk state machine or resilience code modified."
+          fi

          # --- 2. Skip label or commit message marker ---
          if grep -qF ',skip-regression-check,' <<< ",$PR_LABELS,"; then
@@ -63,8 +93,6 @@ jobs:
          fi

          # --- 3. Exempt static-only / docs-only changes ---
-          CHANGED_FILES=$(git diff --name-only "${BASE_REF}...${HEAD_REF}")
-
          if [ -z "$CHANGED_FILES" ]; then
            echo "No changed files — skipping."
            exit 0
@@ -110,5 +138,12 @@ jobs:
          fi

          # --- 5. No tests found ---
-          echo "::warning::This PR looks like a bug fix but contains no test changes. Every fix should include a regression test. Add a #[test] or #[tokio::test], or apply the 'skip-regression-check' label if not feasible."
+          if [ "$IS_FIX" = true ]; then
+            echo "::warning::This PR looks like a bug fix but contains no test changes."
+          fi
+          if [ "$TOUCHES_HIGH_RISK" = true ]; then
+            echo "::warning::This PR modifies high-risk state machine or resilience code but includes no test changes."
+          fi
+          echo "::warning::Please add tests exercising the changed behavior, or apply the 'skip-regression-check' label if not feasible."
          exit 1
+
@@ -17,7 +17,10 @@ jobs:
      matrix:
        include:
          - name: all-features
-            flags: "--features postgres,libsql,html-to-markdown"
+            # Keep product feature coverage broad without pulling in the
+            # test-only `integration` feature, which is exercised separately
+            # in the heavy integration job below.
+            flags: "--no-default-features --features postgres,libsql,html-to-markdown,bedrock,import"
          - name: default
            flags: ""
          - name: libsql-only
@@ -39,6 +42,26 @@ jobs:
      - name: Run Tests
        run: cargo test ${{ matrix.flags }} -- --nocapture

+  heavy-integration-tests:
+    name: Heavy Integration Tests
+    runs-on: ubuntu-latest
+    steps:
+      - name: Checkout repository
+        uses: actions/checkout@v6
+      - name: Install Rust
+        uses: dtolnay/rust-toolchain@stable
+        with:
+          targets: wasm32-wasip2
+      - uses: Swatinem/rust-cache@v2
+        with:
+          key: heavy-integration
+      - name: Build Telegram WASM channel
+        run: cargo build --manifest-path channels-src/telegram/Cargo.toml --target wasm32-wasip2 --release
+      - name: Run thread scheduling integration tests
+        run: cargo test --no-default-features --features libsql,integration --test e2e_thread_scheduling -- --nocapture
+      - name: Run Telegram thread-scope regression test
+        run: cargo test --features integration --test telegram_auth_integration test_private_messages_use_chat_id_as_thread_scope -- --exact
+
  telegram-tests:
    name: Telegram Channel Tests
    if: >
@@ -65,7 +88,7 @@ jobs:
      matrix:
        include:
          - name: all-features
-            flags: "--all-features"
+            flags: "--no-default-features --features postgres,libsql,html-to-markdown,bedrock,import"
          - name: default
            flags: ""
          - name: libsql-only
@@ -149,7 +172,7 @@ jobs:
    name: Run Tests
    runs-on: ubuntu-latest
    if: always()
-    needs: [tests, telegram-tests, wasm-wit-compat, docker-build, windows-build, version-check, bench-compile]
+    needs: [tests, heavy-integration-tests, telegram-tests, wasm-wit-compat, docker-build, windows-build, version-check, bench-compile]
    steps:
      - run: |
          # Unit tests must always pass
@@ -157,6 +180,10 @@ jobs:
            echo "Unit tests failed"
            exit 1
          fi
+          if [[ "${{ needs.heavy-integration-tests.result }}" != "success" ]]; then
+            echo "Heavy integration tests failed"
+            exit 1
+          fi
          # Gated jobs: must pass on promotion PRs / push, skipped on developer PRs
          for job in telegram-tests wasm-wit-compat docker-build windows-build version-check bench-compile; do
            case "$job" in
@@ -33,3 +33,9 @@ trace_*.json
 # Local Claude Code settings (machine-specific, should not be committed)
 .claude/settings.local.json
 .worktrees/
+
+# Python cache
+__pycache__/
+*.pyc
+*.pyo
+*.pyd
@@ -7,6 +7,205 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0

 ## [Unreleased]

+## [0.21.0](https://github.com/nearai/ironclaw/compare/v0.20.0...v0.21.0) - 2026-03-20
+
+### Added
+
+- structured fallback deliverables for failed/stuck jobs ([#236](https://github.com/nearai/ironclaw/pull/236))
+- LRU embedding cache for workspace search ([#1423](https://github.com/nearai/ironclaw/pull/1423))
+- receive relay events via webhook callbacks ([#1254](https://github.com/nearai/ironclaw/pull/1254))
+
+### Fixed
+
+- bump Feishu channel version for promotion
+- *(approval)* make "always" auto-approve work for credentialed HTTP requests ([#1257](https://github.com/nearai/ironclaw/pull/1257))
+- skip NEAR AI session check when backend is not nearai ([#1413](https://github.com/nearai/ironclaw/pull/1413))
+
+### Other
+
+- Make hosted OAuth and MCP auth generic ([#1375](https://github.com/nearai/ironclaw/pull/1375))
+
+## [0.20.0](https://github.com/nearai/ironclaw/compare/v0.19.0...v0.20.0) - 2026-03-19
+
+### Added
+
+- *(self-repair)* wire stuck_threshold, store, and builder ([#712](https://github.com/nearai/ironclaw/pull/712))
+- *(testing)* add FaultInjector framework for StubLlm ([#1233](https://github.com/nearai/ironclaw/pull/1233))
+- *(gateway)* unified settings page with subtabs ([#1191](https://github.com/nearai/ironclaw/pull/1191))
+- upgrade MiniMax default model to M2.7 ([#1357](https://github.com/nearai/ironclaw/pull/1357))
+
+### Fixed
+
+- navigate telegram E2E tests to channels subtab ([#1408](https://github.com/nearai/ironclaw/pull/1408))
+- add missing `builder` field and update E2E extensions tab navigation ([#1400](https://github.com/nearai/ironclaw/pull/1400))
+- remove debug_assert guards that panic on valid error paths ([#1385](https://github.com/nearai/ironclaw/pull/1385))
+- address valid review comments from PR #1359 ([#1380](https://github.com/nearai/ironclaw/pull/1380))
+- full_job routine runs stay running until linked job completion ([#1374](https://github.com/nearai/ironclaw/pull/1374))
+- full_job routine concurrency tracks linked job lifetime ([#1372](https://github.com/nearai/ironclaw/pull/1372))
+- remove -x from coverage pytest to prevent suite-blocking failures ([#1360](https://github.com/nearai/ironclaw/pull/1360))
+- add debug_assert invariant guards to critical code paths ([#1312](https://github.com/nearai/ironclaw/pull/1312))
+- *(mcp)* retry after missing session id errors ([#1355](https://github.com/nearai/ironclaw/pull/1355))
+- *(telegram)* preserve polling after secret-blocked updates ([#1353](https://github.com/nearai/ironclaw/pull/1353))
+- *(llm)* cap retry-after delays ([#1351](https://github.com/nearai/ironclaw/pull/1351))
+- *(setup)* remove nonexistent webhook secret command hint ([#1349](https://github.com/nearai/ironclaw/pull/1349))
+- Rate limiter returns retry after None instead of a duration ([#1269](https://github.com/nearai/ironclaw/pull/1269))
+
+### Other
+
+- bump telegram channel version to 0.2.5 ([#1410](https://github.com/nearai/ironclaw/pull/1410))
+- *(ci)* enforce test requirement for state machine and resilience changes ([#1230](https://github.com/nearai/ironclaw/pull/1230)) ([#1304](https://github.com/nearai/ironclaw/pull/1304))
+- Fix duplicate LLM responses for matched event routines ([#1275](https://github.com/nearai/ironclaw/pull/1275))
+- add Japanese README ([#1306](https://github.com/nearai/ironclaw/pull/1306))
+- *(ci)* add coverage gates via codecov.yml ([#1228](https://github.com/nearai/ironclaw/pull/1228)) ([#1291](https://github.com/nearai/ironclaw/pull/1291))
+- Redesign routine create requests for LLMs ([#1147](https://github.com/nearai/ironclaw/pull/1147))
+
+## [0.19.0](https://github.com/nearai/ironclaw/compare/v0.18.0...v0.19.0) - 2026-03-17
+
+### Added
+
+- verify telegram owner during hot activation ([#1157](https://github.com/nearai/ironclaw/pull/1157))
+- *(config)* unify config resolution with Settings fallback (Phase 2, #1119) ([#1203](https://github.com/nearai/ironclaw/pull/1203))
+- *(sandbox)* add retry logic for transient container failures ([#1232](https://github.com/nearai/ironclaw/pull/1232))
+- *(heartbeat)* fire_at time-of-day scheduling with IANA timezone ([#1029](https://github.com/nearai/ironclaw/pull/1029))
+- Reuse Codex CLI OAuth tokens for ChatGPT backend LLM calls ([#693](https://github.com/nearai/ironclaw/pull/693))
+- add pre-push git hook with delta lint mode ([#833](https://github.com/nearai/ironclaw/pull/833))
+- *(cli)* add `logs` command for gateway log access ([#1105](https://github.com/nearai/ironclaw/pull/1105))
+- add Feishu/Lark WASM channel plugin ([#1110](https://github.com/nearai/ironclaw/pull/1110))
+- add Criterion benchmarks for safety layer hot paths ([#836](https://github.com/nearai/ironclaw/pull/836))
+- *(routines)* human-readable cron schedule summaries in web UI ([#1154](https://github.com/nearai/ironclaw/pull/1154))
+- *(web)* add follow-up suggestion chips and ghost text ([#1156](https://github.com/nearai/ironclaw/pull/1156))
+- *(ci)* include commit history in staging promotion PRs ([#952](https://github.com/nearai/ironclaw/pull/952))
+- *(tools)* add reusable sensitive JSON redaction helper ([#457](https://github.com/nearai/ironclaw/pull/457))
+- configurable hybrid search fusion strategy ([#234](https://github.com/nearai/ironclaw/pull/234))
+- *(cli)* add cron subcommand for managing scheduled routines ([#1017](https://github.com/nearai/ironclaw/pull/1017))
+- adds context-llm tool support ([#616](https://github.com/nearai/ironclaw/pull/616))
+- *(web-chat)* add hover copy button for user/assistant messages ([#948](https://github.com/nearai/ironclaw/pull/948))
+- add Slack approval buttons for tool execution in DMs ([#796](https://github.com/nearai/ironclaw/pull/796))
+- enhance HTTP tool parameter parsing ([#911](https://github.com/nearai/ironclaw/pull/911))
+- *(routines)* enable tool access in lightweight routine execution ([#257](https://github.com/nearai/ironclaw/pull/257)) ([#730](https://github.com/nearai/ironclaw/pull/730))
+- add MiniMax as a built-in LLM provider ([#940](https://github.com/nearai/ironclaw/pull/940))
+- *(cli)* add `ironclaw channels list` subcommand ([#933](https://github.com/nearai/ironclaw/pull/933))
+- *(cli)* add `ironclaw skills list/search/info` subcommands ([#918](https://github.com/nearai/ironclaw/pull/918))
+- add cargo-deny for supply chain safety ([#834](https://github.com/nearai/ironclaw/pull/834))
+- *(setup)* display ASCII art banner during onboarding ([#851](https://github.com/nearai/ironclaw/pull/851))
+- *(extensions)* unify auth and configure into single entrypoint ([#677](https://github.com/nearai/ironclaw/pull/677))
+- *(i18n)* Add internationalization support with Chinese and English translations ([#929](https://github.com/nearai/ironclaw/pull/929))
+- Import OpenClaw memory, history and settings ([#903](https://github.com/nearai/ironclaw/pull/903))
+
+### Fixed
+
+- jobs limit ([#1274](https://github.com/nearai/ironclaw/pull/1274))
+- misleading UI message ([#1265](https://github.com/nearai/ironclaw/pull/1265))
+- bump channel registry versions for promotion ([#1264](https://github.com/nearai/ironclaw/pull/1264))
+- cover staging CI all-features and routine batch regressions ([#1256](https://github.com/nearai/ironclaw/pull/1256))
+- resolve merge conflict fallout and missing config fields
+- web/CLI routine mutations do not refresh live event trigger cache ([#1255](https://github.com/nearai/ironclaw/pull/1255))
+- *(jobs)* make completed->completed transition idempotent to prevent race errors ([#1068](https://github.com/nearai/ironclaw/pull/1068))
+- *(llm)* persist refreshed Anthropic OAuth token after Keychain re-read ([#1213](https://github.com/nearai/ironclaw/pull/1213))
+- *(worker)* prevent orphaned tool_results and fix parallel merging ([#1069](https://github.com/nearai/ironclaw/pull/1069))
+- Telegram bot token validation fails intermittently (HTTP 404) ([#1166](https://github.com/nearai/ironclaw/pull/1166))
+- *(security)* prevent metadata spoofing of internal job monitor flag ([#1195](https://github.com/nearai/ironclaw/pull/1195))
+- *(security)* default webhook server to loopback when tunnel is configured ([#1194](https://github.com/nearai/ironclaw/pull/1194))
+- *(auth)* avoid false success and block chat during pending auth ([#1111](https://github.com/nearai/ironclaw/pull/1111))
+- *(config)* unify ChannelsConfig resolution to env > settings > default ([#1124](https://github.com/nearai/ironclaw/pull/1124))
+- *(web-chat)* normalize chat copy to plain text ([#1114](https://github.com/nearai/ironclaw/pull/1114))
+- *(skill)* treat empty url param as absent when installing skills ([#1128](https://github.com/nearai/ironclaw/pull/1128))
+- preserve AuthError type in oauth_http_client cache ([#1152](https://github.com/nearai/ironclaw/pull/1152))
+- *(web)* prevent Safari IME composition Enter from sending message ([#1140](https://github.com/nearai/ironclaw/pull/1140))
+- *(mcp)* handle 400 auth errors, clear auth mode after OAuth, trim tokens ([#1158](https://github.com/nearai/ironclaw/pull/1158))
+- eliminate panic paths in production code ([#1184](https://github.com/nearai/ironclaw/pull/1184))
+- N+1 query pattern in event trigger loop (routine_engine) ([#1163](https://github.com/nearai/ironclaw/pull/1163))
+- *(llm)* add stop_sequences parity for tool completions ([#1170](https://github.com/nearai/ironclaw/pull/1170))
+- *(channels)* use live owner binding during wasm hot activation ([#1171](https://github.com/nearai/ironclaw/pull/1171))
+- Non-transactional multi-step context updates between metadata/to… ([#1161](https://github.com/nearai/ironclaw/pull/1161))
+- *(webhook)* avoid lock-held awaits in server lifecycle paths ([#1168](https://github.com/nearai/ironclaw/pull/1168))
+- Google Sheets returns 403 PERMISSION_DENIED after completing OAuth ([#1164](https://github.com/nearai/ironclaw/pull/1164))
+- HTTP webhook secret transmitted in request body rather than via header, docs inconsistency and security concern ([#1162](https://github.com/nearai/ironclaw/pull/1162))
+- *(ci)* exclude ironclaw_safety from release automation ([#1146](https://github.com/nearai/ironclaw/pull/1146))
+- *(registry)* bump versions for github, web-search, and discord extensions ([#1106](https://github.com/nearai/ironclaw/pull/1106))
+- *(mcp)* address 14 audit findings across MCP module ([#1094](https://github.com/nearai/ironclaw/pull/1094))
+- *(http)* replace .expect() with match in webhook handler ([#1133](https://github.com/nearai/ironclaw/pull/1133))
+- *(time)* treat empty timezone string as absent ([#1127](https://github.com/nearai/ironclaw/pull/1127))
+- 5 critical/high-priority bugs (auth bypass, relay failures, unbounded recursion, context growth) ([#1083](https://github.com/nearai/ironclaw/pull/1083))
+- *(ci)* checkout promotion PR head for metadata refresh ([#1097](https://github.com/nearai/ironclaw/pull/1097))
+- *(ci)* add missing attachments field and crates/ dir to Dockerfiles ([#1100](https://github.com/nearai/ironclaw/pull/1100))
+- *(registry)* bump telegram channel version for capabilities change ([#1064](https://github.com/nearai/ironclaw/pull/1064))
+- *(ci)* repair staging promotion workflow behavior ([#1091](https://github.com/nearai/ironclaw/pull/1091))
+- *(wasm)* address #1086 review followups -- description hint and coercion safety ([#1092](https://github.com/nearai/ironclaw/pull/1092))
+- *(ci)* repair staging-ci workflow parsing ([#1090](https://github.com/nearai/ironclaw/pull/1090))
+- *(extensions)* fix lifecycle bugs + comprehensive E2E tests ([#1070](https://github.com/nearai/ironclaw/pull/1070))
+- add tool_info schema discovery for WASM tools ([#1086](https://github.com/nearai/ironclaw/pull/1086))
+- resolve bug_bash UX/logging issues (#1054 #1055 #1058) ([#1072](https://github.com/nearai/ironclaw/pull/1072))
+- *(http)* fail closed when webhook secret is missing at runtime ([#1075](https://github.com/nearai/ironclaw/pull/1075))
+- *(service)* set CLI_ENABLED=false in macOS launchd plist ([#1079](https://github.com/nearai/ironclaw/pull/1079))
+- relax approval requirements for low-risk tools ([#922](https://github.com/nearai/ironclaw/pull/922))
+- *(web)* make approval requests appear without page reload ([#996](https://github.com/nearai/ironclaw/pull/996)) ([#1073](https://github.com/nearai/ironclaw/pull/1073))
+- *(routines)* run cron checks immediately on ticker startup ([#1066](https://github.com/nearai/ironclaw/pull/1066))
+- *(web)* recompute cron next_fire_at when re-enabling routines ([#1080](https://github.com/nearai/ironclaw/pull/1080))
+- *(memory)* reject absolute filesystem paths with corrective routing ([#934](https://github.com/nearai/ironclaw/pull/934))
+- remove all inline event handlers for CSP script-src compliance ([#1063](https://github.com/nearai/ironclaw/pull/1063))
+- *(mcp)* include OAuth state parameter in authorization URLs ([#1049](https://github.com/nearai/ironclaw/pull/1049))
+- *(mcp)* open MCP OAuth in same browser as gateway ([#951](https://github.com/nearai/ironclaw/pull/951))
+- *(deploy)* harden production container and bootstrap security ([#1014](https://github.com/nearai/ironclaw/pull/1014))
+- release lock guards before awaiting channel send ([#869](https://github.com/nearai/ironclaw/pull/869)) ([#1003](https://github.com/nearai/ironclaw/pull/1003))
+- *(registry)* use versioned artifact URLs and checksums for all WASM manifests ([#1007](https://github.com/nearai/ironclaw/pull/1007))
+- *(setup)* preserve model selection on provider re-run ([#679](https://github.com/nearai/ironclaw/pull/679)) ([#987](https://github.com/nearai/ironclaw/pull/987))
+- *(mcp)* attach session manager for non-OAuth HTTP clients ([#793](https://github.com/nearai/ironclaw/pull/793)) ([#986](https://github.com/nearai/ironclaw/pull/986))
+- *(security)* migrate webhook auth to HMAC-SHA256 signature header ([#970](https://github.com/nearai/ironclaw/pull/970))
+- *(security)* make unsafe env::set_var calls safe with explicit invariants ([#968](https://github.com/nearai/ironclaw/pull/968))
+- *(security)* require explicit SANDBOX_ALLOW_FULL_ACCESS to enable FullAccess policy ([#967](https://github.com/nearai/ironclaw/pull/967))
+- *(security)* add Content-Security-Policy header to web gateway ([#966](https://github.com/nearai/ironclaw/pull/966))
+- *(test)* stabilize openai compat oversized-body regression ([#839](https://github.com/nearai/ironclaw/pull/839))
+- *(ci)* disambiguate WASM bundle filenames to prevent tool/channel collision ([#964](https://github.com/nearai/ironclaw/pull/964))
+- *(setup)* validate channel credentials during setup ([#684](https://github.com/nearai/ironclaw/pull/684))
+- drain tunnel pipes to prevent zombie process ([#735](https://github.com/nearai/ironclaw/pull/735))
+- *(mcp)* header safety validation and Authorization conflict bug from #704 ([#752](https://github.com/nearai/ironclaw/pull/752))
+- *(agent)* block thread_id-based context pollution across users ([#760](https://github.com/nearai/ironclaw/pull/760))
+- *(mcp)* stdio/unix transports skip initialize handshake ([#890](https://github.com/nearai/ironclaw/pull/890)) ([#935](https://github.com/nearai/ironclaw/pull/935))
+- *(setup)* drain residual events and filter key kind in onboard prompts ([#937](https://github.com/nearai/ironclaw/pull/937)) ([#949](https://github.com/nearai/ironclaw/pull/949))
+- *(security)* load WASM tool description and schema from capabilities.json ([#520](https://github.com/nearai/ironclaw/pull/520))
+- *(security)* resolve DNS once and reuse for SSRF validation to prevent rebinding ([#518](https://github.com/nearai/ironclaw/pull/518))
+- *(security)* replace regex HTML sanitizer with DOMPurify to prevent XSS ([#510](https://github.com/nearai/ironclaw/pull/510))
+- *(ci)* improve Claude Code review reliability ([#955](https://github.com/nearai/ironclaw/pull/955))
+- *(ci)* run gated test jobs during staging CI ([#956](https://github.com/nearai/ironclaw/pull/956))
+- *(ci)* prevent staging-ci tag failure and chained PR auto-close ([#900](https://github.com/nearai/ironclaw/pull/900))
+- *(ci)* WASM WIT compat sqlite3 duplicate symbol conflict ([#953](https://github.com/nearai/ironclaw/pull/953))
+- resolve deferred review items from PRs #883, #848, #788 ([#915](https://github.com/nearai/ironclaw/pull/915))
+- *(web)* improve UX readability and accessibility in chat UI ([#910](https://github.com/nearai/ironclaw/pull/910))
+
+### Other
+
+- Fix Telegram auto-verify flow and routing ([#1273](https://github.com/nearai/ironclaw/pull/1273))
+- *(e2e)* fix approval waiting regression coverage ([#1270](https://github.com/nearai/ironclaw/pull/1270))
+- isolate heavy integration tests ([#1266](https://github.com/nearai/ironclaw/pull/1266))
+- Merge branch 'main' into fix/resolve-conflicts
+- Refactor owner scope across channels and fix default routing fallback ([#1151](https://github.com/nearai/ironclaw/pull/1151))
+- *(extensions)* document relay manager init order ([#928](https://github.com/nearai/ironclaw/pull/928))
+- *(setup)* extract init logic from wizard into owning modules ([#1210](https://github.com/nearai/ironclaw/pull/1210))
+- mention MiniMax as built-in provider in all READMEs ([#1209](https://github.com/nearai/ironclaw/pull/1209))
+- Fix schema-guided tool parameter coercion ([#1143](https://github.com/nearai/ironclaw/pull/1143))
+- Make no-panics CI check test-aware ([#1160](https://github.com/nearai/ironclaw/pull/1160))
+- *(mcp)* avoid reallocating SSE buffer on each chunk ([#1153](https://github.com/nearai/ironclaw/pull/1153))
+- *(routines)* avoid full message history clone each tool iteration ([#1172](https://github.com/nearai/ironclaw/pull/1172))
+- *(registry)* align manifest versions with published artifacts ([#1169](https://github.com/nearai/ironclaw/pull/1169))
+- remove __pycache__ from repo and add to .gitignore ([#1177](https://github.com/nearai/ironclaw/pull/1177))
+- *(registry)* move MCP servers from code to JSON manifests ([#1144](https://github.com/nearai/ironclaw/pull/1144))
+- improve routine schema guidance ([#1089](https://github.com/nearai/ironclaw/pull/1089))
+- add event-trigger routine e2e coverage ([#1088](https://github.com/nearai/ironclaw/pull/1088))
+- enforce no .unwrap(), .expect(), or assert!() in production code ([#1087](https://github.com/nearai/ironclaw/pull/1087))
+- periodic sync main into staging (resolved conflicts) ([#1098](https://github.com/nearai/ironclaw/pull/1098))
+- fix formatting in cli/mod.rs and mcp/auth.rs ([#1071](https://github.com/nearai/ironclaw/pull/1071))
+- Expose the shared agent session manager via AppComponents ([#532](https://github.com/nearai/ironclaw/pull/532))
+- *(agent)* remove unnecessary Worker re-export ([#923](https://github.com/nearai/ironclaw/pull/923))
+- Fix UTF-8 unsafe truncation in WASM emit_message ([#1015](https://github.com/nearai/ironclaw/pull/1015))
+- extract safety module into ironclaw_safety crate ([#1024](https://github.com/nearai/ironclaw/pull/1024))
+- Add Z.AI provider support for GLM-5 ([#938](https://github.com/nearai/ironclaw/pull/938))
+- *(html_to_markdown)* refresh golden files after renderer bump ([#1016](https://github.com/nearai/ironclaw/pull/1016))
+- Migrate GitHub webhook normalization into github tool ([#758](https://github.com/nearai/ironclaw/pull/758))
+- Fix systemctl unit ([#472](https://github.com/nearai/ironclaw/pull/472))
+- add Russian localization (README.ru.md) ([#850](https://github.com/nearai/ironclaw/pull/850))
+- Add generic host-verified /webhook/tools/{tool} ingress ([#757](https://github.com/nearai/ironclaw/pull/757))
+
 ## [0.18.0](https://github.com/nearai/ironclaw/compare/v0.17.0...v0.18.0) - 2026-03-11

 ### Other
@@ -3436,7 +3436,7 @@ dependencies = [

 [[package]]
 name = "ironclaw"
-version = "0.18.0"
+version = "0.21.0"
 dependencies = [
 "aes-gcm",
 "aho-corasick",
@@ -3461,6 +3461,7 @@ dependencies = [
 "dirs 6.0.0",
 "dotenvy",
 "ed25519-dalek",
+ "eventsource-stream",
 "flate2",
 "fs4",
 "futures",
@@ -4364,9 +4365,9 @@ dependencies = [

 [[package]]
 name = "openssl"
-version = "0.10.75"
+version = "0.10.76"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "08838db121398ad17ab8531ce9de97b244589089e290a384c900cb9ff7434328"
+checksum = "951c002c75e16ea2c65b8c7e4d3d51d5530d8dfa7d060b4776828c88cfb18ecf"
 dependencies = [
 "bitflags 2.11.0",
 "cfg-if",
@@ -4402,9 +4403,9 @@ checksum = "7c87def4c32ab89d880effc9e097653c8da5d6ef28e6b539d313baaacfbafcbe"

 [[package]]
 name = "openssl-sys"
-version = "0.9.111"
+version = "0.9.112"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "82cab2d520aa75e3c58898289429321eb788c3106963d0dc886ec7a5f4adc321"
+checksum = "57d55af3b3e226502be1526dfdba67ab0e9c96fc293004e79576b2b9edb0dbdb"
 dependencies = [
 "cc",
 "libc",
@@ -20,7 +20,7 @@ exclude = [

 [package]
 name = "ironclaw"
-version = "0.18.0"
+version = "0.21.0"
 edition = "2024"
 rust-version = "1.92"
 description = "Secure personal AI assistant that protects your data and expands its capabilities on the fly"
@@ -40,6 +40,7 @@ eula = false
 tokio = { version = "1", features = ["full"] }
 tokio-stream = { version = "0.1", features = ["sync"] }
 futures = "0.3"
+eventsource-stream = "0.2"

 # HTTP client
 reqwest = { version = "0.12", default-features = false, features = ["json", "multipart", "rustls-tls-native-roots", "stream"] }
@@ -221,11 +222,17 @@ postgres = [
    "rust_decimal/db-tokio-postgres",
 ]
 libsql = ["dep:libsql"]
+# Opt-in feature for especially heavy integration-test targets that run in a
+# dedicated CI job instead of the default Rust test matrix.
 integration = []
 html-to-markdown = ["dep:html-to-markdown-rs", "dep:readabilityrs"]
 bedrock = ["dep:aws-config", "dep:aws-sdk-bedrockruntime", "dep:aws-smithy-types"]
 import = ["dep:json5", "libsql"]

+[[test]]
+name = "e2e_thread_scheduling"
+required-features = ["libsql", "integration"]
+
 [[test]]
 name = "html_to_markdown"
 required-features = ["html-to-markdown"]
@@ -20,9 +20,9 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 |---------|----------|----------|-------|
 | Hub-and-spoke architecture | ✅ | ✅ | Web gateway as central hub |
 | WebSocket control plane | ✅ | ✅ | Gateway with WebSocket + SSE |
-| Single-user system | ✅ | ✅ | |
+| Single-user system | ✅ | ✅ | Explicit instance owner scope for persistent routines, secrets, jobs, settings, extensions, and workspace memory |
 | Multi-agent routing | ✅ | ❌ | Workspace isolation per-agent |
-| Session-based messaging | ✅ | ✅ | Per-sender sessions |
+| Session-based messaging | ✅ | ✅ | Owner scope is separate from sender identity and conversation scope |
 | Loopback-first networking | ✅ | ✅ | HTTP binds to 0.0.0.0 but can be configured |

 ### Owner: _Unassigned_
@@ -66,9 +66,9 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | CLI/TUI | ✅ | ✅ | - | Ratatui-based TUI |
 | HTTP webhook | ✅ | ✅ | - | axum with secret validation |
 | REPL (simple) | ✅ | ✅ | - | For testing |
-| WASM channels | ❌ | ✅ | - | IronClaw innovation |
+| WASM channels | ❌ | ✅ | - | IronClaw innovation; host resolves owner scope vs sender identity |
 | WhatsApp | ✅ | ❌ | P1 | Baileys (Web), same-phone mode with echo detection |
-| Telegram | ✅ | ✅ | - | WASM channel(MTProto), DM pairing, caption, /start, bot_username, DM topics |
+| Telegram | ✅ | ✅ | - | WASM channel(MTProto), DM pairing, caption, /start, bot_username, DM topics, setup-time owner auto-verification, owner-scoped persistence |
 | Discord | ✅ | ❌ | P2 | discord.js, thread parent binding inheritance |
 | Signal | ✅ | ✅ | P2 | signal-cli daemonPC, SSE listener HTTP/JSON-R, user/group allowlists, DM pairing |
 | Slack | ✅ | ✅ | - | WASM tool |
@@ -465,7 +465,7 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | Device pairing | ✅ | ❌ | |
 | Tailscale identity | ✅ | ❌ | |
 | Trusted-proxy auth | ✅ | ❌ | Header-based reverse proxy auth |
-| OAuth flows | ✅ | 🚧 | NEAR AI OAuth |
+| OAuth flows | ✅ | 🚧 | NEAR AI OAuth plus hosted extension/MCP OAuth broker; external auth-proxy rollout still pending |
 | DM pairing verification | ✅ | ✅ | ironclaw pairing approve, host APIs |
 | Allowlist/blocklist | ✅ | 🚧 | allow_from + pairing store |
 | Per-group tool policies | ✅ | ❌ | |
@@ -0,0 +1,330 @@
+<p align="center">
+  <img src="ironclaw.png?v=2" alt="IronClaw" width="200"/>
+</p>
+
+<h1 align="center">IronClaw</h1>
+
+<p align="center">
+  <strong>あなたの味方になる、安全なパーソナルAIアシスタント</strong>
+</p>
+
+<p align="center">
+  <a href="#license"><img src="https://img.shields.io/badge/license-MIT%20OR%20Apache%202.0-blue.svg" alt="License: MIT OR Apache-2.0" /></a>
+  <a href="https://t.me/ironclawAI"><img src="https://img.shields.io/badge/Telegram-%40ironclawAI-26A5E4?style=flat&logo=telegram&logoColor=white" alt="Telegram: @ironclawAI" /></a>
+  <a href="https://www.reddit.com/r/ironclawAI/"><img src="https://img.shields.io/badge/Reddit-r%2FironclawAI-FF4500?style=flat&logo=reddit&logoColor=white" alt="Reddit: r/ironclawAI" /></a>
+</p>
+
+<p align="center">
+  <a href="README.md">English</a> |
+  <a href="README.zh-CN.md">简体中文</a> |
+  <a href="README.ru.md">Русский</a> |
+  <a href="README.ja.md">日本語</a>
+</p>
+
+<p align="center">
+  <a href="#フィロソフィー">フィロソフィー</a> •
+  <a href="#機能">機能</a> •
+  <a href="#インストール">インストール</a> •
+  <a href="#設定">設定</a> •
+  <a href="#セキュリティ">セキュリティ</a> •
+  <a href="#アーキテクチャ">アーキテクチャ</a>
+</p>
+
+---
+
+## フィロソフィー
+
+IronClawはシンプルな原則に基づいて構築されています：**あなたのAIアシスタントは、あなたのために働くべきであり、あなたに不利益をもたらすべきではありません。**
+
+AIシステムがデータの取り扱いについて不透明になり、企業の利益に沿って調整されることが増えている世界で、IronClawは異なるアプローチを取ります：
+
+- **あなたのデータはあなたのもの** - すべての情報はローカルに保存・暗号化され、あなたの管理下から離れることはありません
+- **設計段階からの透明性** - オープンソース、監査可能、隠れたテレメトリやデータ収集なし
+- **自己拡張する能力** - ベンダーのアップデートを待たずに、新しいツールをその場で構築
+- **多層防御** - 複数のセキュリティレイヤーがプロンプトインジェクションやデータ流出から保護
+
+IronClawは、個人生活にも仕事にも本当に信頼できるAIアシスタントです。
+
+## 機能
+
+### セキュリティファースト
+
+- **WASMサンドボックス** - 信頼されていないツールは、機能ベースの権限を持つ隔離されたWebAssemblyコンテナで実行
+- **認証情報の保護** - シークレットはツールに公開されず、リーク検出付きでホスト境界で注入
+- **プロンプトインジェクション防御** - パターン検出、コンテンツサニタイズ、ポリシー適用
+- **エンドポイントの許可リスト** - HTTPリクエストは明示的に許可されたホストとパスのみに制限
+
+### 常時利用可能
+
+- **マルチチャネル** - REPL、HTTPウェブフック、WASMチャネル（Telegram、Slack）、Webゲートウェイ
+- **Dockerサンドボックス** - ジョブごとのトークンとオーケストレーター/ワーカーパターンによる隔離されたコンテナ実行
+- **Webゲートウェイ** - リアルタイムSSE/WebSocketストリーミング対応のブラウザUI
+- **ルーティン** - cronスケジュール、イベントトリガー、ウェブフックハンドラーによるバックグラウンド自動化
+- **ハートビートシステム** - 監視・保守タスクのためのプロアクティブなバックグラウンド実行
+- **並列ジョブ** - 隔離されたコンテキストで複数のリクエストを同時に処理
+- **自己修復** - スタックした操作の自動検出と復旧
+
+### 自己拡張
+
+- **動的ツール構築** - 必要なものを説明すると、IronClawがWASMツールとして構築
+- **MCPプロトコル** - Model Context Protocolサーバーに接続して追加機能を利用
+- **プラグインアーキテクチャ** - 再起動なしで新しいWASMツールやチャネルを追加
+
+### 永続メモリ
+
+- **ハイブリッド検索** - Reciprocal Rank Fusionを使用した全文検索+ベクトル検索
+- **ワークスペースファイルシステム** - メモ、ログ、コンテキストのための柔軟なパスベースストレージ
+- **アイデンティティファイル** - セッション間で一貫した人格と設定を維持
+
+## インストール
+
+### 前提条件
+
+- Rust 1.85+
+- PostgreSQL 15+ ([pgvector](https://github.com/pgvector/pgvector)拡張機能を含む)
+- NEAR AIアカウント（セットアップウィザードで認証を処理）
+
+## ダウンロードまたはビルド
+
+最新のアップデートは[リリースページ](https://github.com/nearai/ironclaw/releases/)をご覧ください。
+
+<details>
+  <summary>Windowsインストーラーでインストール（Windows）</summary>
+
+[Windowsインストーラー](https://github.com/nearai/ironclaw/releases/latest/download/ironclaw-x86_64-pc-windows-msvc.msi)をダウンロードして実行してください。
+
+</details>
+
+<details>
+  <summary>PowerShellスクリプトでインストール（Windows）</summary>
+
+```sh
+irm https://github.com/nearai/ironclaw/releases/latest/download/ironclaw-installer.ps1 | iex
+```
+
+</details>
+
+<details>
+  <summary>シェルスクリプトでインストール（macOS、Linux、Windows/WSL）</summary>
+
+```sh
+curl --proto '=https' --tlsv1.2 -LsSf https://github.com/nearai/ironclaw/releases/latest/download/ironclaw-installer.sh | sh
+```
+</details>
+
+<details>
+  <summary>Homebrewでインストール（macOS/Linux）</summary>
+
+```sh
+brew install ironclaw
+```
+
+</details>
+
+<details>
+  <summary>ソースコードからコンパイル（Windows、Linux、macOSでCargo）</summary>
+
+`cargo`でインストールします。コンピューターに[Rust](https://rustup.rs)がインストールされていることを確認してください。
+
+```bash
+# リポジトリをクローン
+git clone https://github.com/nearai/ironclaw.git
+cd ironclaw
+
+# ビルド
+cargo build --release
+
+# テストを実行
+cargo test
+```
+
+**フルリリース**（チャネルソースを変更した後）の場合、まず`./scripts/build-all.sh`を実行してチャネルを再ビルドしてください。
+
+</details>
+
+### データベースのセットアップ
+
+```bash
+# データベースを作成
+createdb ironclaw
+
+# pgvectorを有効化
+psql ironclaw -c "CREATE EXTENSION IF NOT EXISTS vector;"
+```
+
+## 設定
+
+セットアップウィザードを実行してIronClawを設定します：
+
+```bash
+ironclaw onboard
+```
+
+ウィザードは、データベース接続、NEAR AI認証（ブラウザOAuth経由）、シークレットの暗号化（システムキーチェーンを使用）を処理します。設定は接続されたデータベースに永続化されます。ブートストラップ変数（例：`DATABASE_URL`、`LLM_BACKEND`）は、データベース接続前に利用できるよう`~/.ironclaw/.env`に書き込まれます。
+
+### 代替LLMプロバイダー
+
+IronClawはデフォルトでNEAR AIを使用しますが、多くのLLMプロバイダーをすぐに利用できます。組み込みプロバイダーには**Anthropic**、**OpenAI**、**Google Gemini**、**MiniMax**、**Mistral**、**Ollama**（ローカル）が含まれます。**OpenRouter**（300以上のモデル）、**Together AI**、**Fireworks AI**、セルフホストサーバー（**vLLM**、**LiteLLM**）などのOpenAI互換サービスもサポートされています。
+
+ウィザードでプロバイダーを選択するか、環境変数を直接設定してください：
+
+```env
+# 例：MiniMax（組み込み、204Kコンテキスト）
+LLM_BACKEND=minimax
+MINIMAX_API_KEY=...
+
+# 例：OpenAI互換エンドポイント
+LLM_BACKEND=openai_compatible
+LLM_BASE_URL=https://openrouter.ai/api/v1
+LLM_API_KEY=sk-or-...
+LLM_MODEL=anthropic/claude-sonnet-4
+```
+
+完全なプロバイダーガイドは[docs/LLM_PROVIDERS.md](docs/LLM_PROVIDERS.md)をご覧ください。
+
+## セキュリティ
+
+IronClawは、データを保護し悪用を防ぐために多層防御を実装しています。
+
+### WASMサンドボックス
+
+すべての信頼されていないツールは、隔離されたWebAssemblyコンテナで実行されます：
+
+- **機能ベースの権限** - HTTP、シークレット、ツール呼び出しの明示的なオプトイン
+- **エンドポイントの許可リスト** - 許可されたホスト/パスへのHTTPリクエストのみ
+- **認証情報の注入** - シークレットはホスト境界で注入され、WASMコードに公開されない
+- **リーク検出** - リクエストとレスポンスのシークレット流出試行をスキャン
+- **レート制限** - 悪用防止のためのツールごとのリクエスト制限
+- **リソース制限** - メモリ、CPU、実行時間の制約
+
+```
+WASM ──► 許可リスト ──► リーク    ──► 認証情報 ──► リクエスト ──► リーク    ──► WASM
+         バリデーター    スキャン       注入        実行          スキャン
+                       (リクエスト)                             (レスポンス)
+```
+
+### プロンプトインジェクション防御
+
+外部コンテンツは複数のセキュリティレイヤーを通過します：
+
+- パターンベースのインジェクション試行検出
+- コンテンツのサニタイズとエスケープ
+- 重要度レベル付きポリシールール（ブロック/警告/レビュー/サニタイズ）
+- 安全なLLMコンテキスト注入のためのツール出力ラッピング
+
+### データ保護
+
+- すべてのデータはローカルのPostgreSQLデータベースに保存
+- AES-256-GCMでシークレットを暗号化
+- テレメトリ、分析、データ共有なし
+- すべてのツール実行の完全な監査ログ
+
+## アーキテクチャ
+
+```
+┌────────────────────────────────────────────────────────────────┐
+│                          チャネル                               │
+│  ┌──────┐  ┌──────┐   ┌─────────────┐  ┌─────────────┐         │
+│  │ REPL │  │ HTTP │   │WASMチャネル │  │ Web         │         │
+│  └──┬───┘  └──┬───┘   └──────┬──────┘  │ ゲートウェイ│         │
+│     │         │              │         │(SSE + WS)   │         │
+│     │         │              │         └──────┬──────┘         │
+│     └─────────┴──────────────┴────────────────┘                │
+│                              │                                 │
+│                    ┌─────────▼─────────┐                       │
+│                    │  エージェントループ │  インテントルーティング│
+│                    └────┬──────────┬───┘                       │
+│                         │          │                           │
+│              ┌──────────▼────┐  ┌──▼───────────────┐           │
+│              │ スケジューラー │  │ ルーティン       │           │
+│              │ (並列ジョブ)  │  │ エンジン         │           │
+│              └──────┬────────┘  │(cron,event,wh)   │           │
+│                     │           └────────┬─────────┘           │
+│       ┌─────────────┼────────────────────┘                     │
+│       │             │                                          │
+│   ┌───▼─────┐  ┌────▼────────────────┐                         │
+│   │ ローカル │  │  オーケストレーター  │                         │
+│   │ ワーカー │  │  ┌───────────────┐  │                         │
+│   │(プロセス │  │  │ Docker        │  │                         │
+│   │ 内)     │  │  │ サンドボックス│  │                         │
+│   └───┬─────┘  │  │ コンテナ      │  │                         │
+│       │        │  │ ┌───────────┐ │  │                         │
+│       │        │  │ │Worker / CC│ │  │                         │
+│       │        │  │ └───────────┘ │  │                         │
+│       │        │  └───────────────┘  │                         │
+│       │        └─────────┬───────────┘                         │
+│       └──────────────────┤                                     │
+│                          │                                     │
+│              ┌───────────▼──────────┐                          │
+│              │   ツールレジストリ    │                          │
+│              │ 組み込み, MCP, WASM  │                          │
+│              └──────────────────────┘                          │
+└────────────────────────────────────────────────────────────────┘
+```
+
+### コアコンポーネント
+
+| コンポーネント | 目的 |
+|---------------|------|
+| **エージェントループ** | メインのメッセージ処理とジョブの調整 |
+| **ルーター** | ユーザーの意図を分類（コマンド、クエリ、タスク） |
+| **スケジューラー** | 優先度付きの並列ジョブ実行を管理 |
+| **ワーカー** | LLM推論とツール呼び出しでジョブを実行 |
+| **オーケストレーター** | コンテナのライフサイクル、LLMプロキシ、ジョブごとの認証 |
+| **Webゲートウェイ** | チャット、メモリ、ジョブ、ログ、拡張機能、ルーティンのブラウザUI |
+| **ルーティンエンジン** | スケジュール（cron）とリアクティブ（イベント、ウェブフック）のバックグラウンドタスク |
+| **ワークスペース** | ハイブリッド検索付き永続メモリ |
+| **セーフティレイヤー** | プロンプトインジェクション防御とコンテンツサニタイズ |
+
+## 使い方
+
+```bash
+# 初回セットアップ（データベース、認証などを設定）
+ironclaw onboard
+
+# インタラクティブREPLを起動
+cargo run
+
+# デバッグログ付き
+RUST_LOG=ironclaw=debug cargo run
+```
+
+## 開発
+
+```bash
+# コードフォーマット
+cargo fmt
+
+# リント
+cargo clippy --all --benches --tests --examples --all-features
+
+# テスト実行
+createdb ironclaw_test
+cargo test
+
+# 特定のテストを実行
+cargo test test_name
+```
+
+- **Telegramチャネル**: セットアップとDMペアリングについては[docs/TELEGRAM_SETUP.md](docs/TELEGRAM_SETUP.md)を参照してください。
+- **チャネルソースの変更**: `cargo build`の前に`./channels-src/telegram/build.sh`を実行して、更新されたWASMをバンドルしてください。
+
+## OpenClawの系譜
+
+IronClawは[OpenClaw](https://github.com/openclaw/openclaw)にインスパイアされたRust再実装です。完全な対応表は[FEATURE_PARITY.md](FEATURE_PARITY.md)をご覧ください。
+
+主な違い：
+
+- **Rust vs TypeScript** - ネイティブパフォーマンス、メモリ安全性、シングルバイナリ
+- **WASMサンドボックス vs Docker** - 軽量、機能ベースのセキュリティ
+- **PostgreSQL vs SQLite** - 本番環境対応の永続化
+- **セキュリティファースト設計** - 複数の防御レイヤー、認証情報の保護
+
+## ライセンス
+
+以下のいずれかのライセンスの下で提供されています：
+
+- Apache License, Version 2.0 ([LICENSE-APACHE](LICENSE-APACHE))
+- MIT License ([LICENSE-MIT](LICENSE-MIT))
+
+お好みに応じて選択してください。
@@ -17,7 +17,8 @@
 <p align="center">
  <a href="README.md">English</a> |
  <a href="README.zh-CN.md">简体中文</a> |
-  <a href="README.ru.md">Русский</a>
+  <a href="README.ru.md">Русский</a> |
+  <a href="README.ja.md">日本語</a>
 </p>

 <p align="center">
@@ -17,7 +17,8 @@
 <p align="center">
  <a href="README.md">English</a> |
  <a href="README.zh-CN.md">简体中文</a> |
-  <a href="README.ru.md">Русский</a>
+  <a href="README.ru.md">Русский</a> |
+  <a href="README.ja.md">日本語</a>
 </p>

 <p align="center">
@@ -17,7 +17,8 @@
 <p align="center">
  <a href="README.md">English</a> |
  <a href="README.zh-CN.md">简体中文</a> |
-  <a href="README.ru.md">Русский</a>
+  <a href="README.ru.md">Русский</a> |
+  <a href="README.ja.md">日本語</a>
 </p>

 <p align="center">
@@ -61,7 +61,7 @@ fn bench_validate_tool_params(c: &mut Criterion) {
    let validator = Validator::new();

    let simple_params: serde_json::Value =
-        serde_json::from_str(r#"{"command": "echo hello"}"#).unwrap(); // safety: bench-only constant JSON
+        serde_json::from_str(r#"{"command": "echo hello"}"#).unwrap();

    let complex_params: serde_json::Value = serde_json::from_str(
        r#"{
@@ -73,7 +73,7 @@ fn bench_validate_tool_params(c: &mut Criterion) {
        "capture_output": true
    }"#,
    )
-    .unwrap(); // safety: bench-only constant JSON
+    .unwrap();

    // Deeply nested JSON to stress the recursive validation walk
    let nested_params: serde_json::Value = serde_json::from_str(
@@ -84,7 +84,7 @@ fn bench_validate_tool_params(c: &mut Criterion) {
        "env": {"KEY1": "val1", "KEY2": "val2", "KEY3": "val3", "KEY4": "val4"}
    }"#,
    )
-    .unwrap(); // safety: bench-only constant JSON
+    .unwrap();

    group.bench_function("simple", |b| {
        b.iter(|| validator.validate_tool_params(black_box(&simple_params)))
@@ -206,9 +206,17 @@ struct FeishuApiResponse<T> {
    data: Option<T>,
 }

-/// Tenant access token response.
-#[derive(Debug, Default, Deserialize)]
-struct TenantAccessTokenData {
+/// Tenant access token response (flat format).
+///
+/// Unlike most Feishu APIs that nest results under `data`, the
+/// `/auth/v3/tenant_access_token/internal` endpoint returns `code`, `msg`,
+/// `tenant_access_token`, and `expire` at the top level.
+#[derive(Debug, Deserialize)]
+struct TenantAccessTokenResponse {
+    #[serde(default)]
+    code: i32,
+    #[serde(default)]
+    msg: String,
    tenant_access_token: String,
    expire: i64,
 }
@@ -770,9 +778,8 @@ fn obtain_tenant_token(api_base: &str) -> Result<String, String> {
                ));
            }

-            let token_resp: FeishuApiResponse<TenantAccessTokenData> =
-                serde_json::from_slice(&response.body)
-                    .map_err(|e| format!("Failed to parse token response: {}", e))?;
+            let token_resp: TenantAccessTokenResponse = serde_json::from_slice(&response.body)
+                .map_err(|e| format!("Failed to parse token response: {}", e))?;

            if token_resp.code != 0 {
                return Err(format!(
@@ -781,23 +788,33 @@ fn obtain_tenant_token(api_base: &str) -> Result<String, String> {
                ));
            }

-            let data = token_resp
-                .data
-                .ok_or_else(|| "Token response missing data".to_string())?;
+            if token_resp.tenant_access_token.is_empty() {
+                return Err("Token response missing tenant_access_token".to_string());
+            }
+
+            if token_resp.expire <= 0 {
+                return Err(format!(
+                    "Token response has invalid expire value: {}",
+                    token_resp.expire
+                ));
+            }

            // Cache the token with expiry.
            let now = channel_host::now_millis();
-            let expiry = now + (data.expire as u64) * 1000;
+            let expiry = now.saturating_add((token_resp.expire as u64).saturating_mul(1000));

-            let _ = channel_host::workspace_write(TOKEN_PATH, &data.tenant_access_token);
+            let _ = channel_host::workspace_write(TOKEN_PATH, &token_resp.tenant_access_token);
            let _ = channel_host::workspace_write(TOKEN_EXPIRY_PATH, &expiry.to_string());

            channel_host::log(
                channel_host::LogLevel::Debug,
-                &format!("Tenant access token refreshed, expires in {}s", data.expire),
+                &format!(
+                    "Tenant access token refreshed, expires in {}s",
+                    token_resp.expire
+                ),
            );

-            Ok(data.tenant_access_token)
+            Ok(token_resp.tenant_access_token)
        }
        Err(e) => Err(format!("Token exchange request failed: {}", e)),
    }
@@ -819,3 +836,60 @@ fn json_response(status: u16, body: serde_json::Value) -> OutgoingHttpResponse {
        body: body_bytes,
    }
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn parse_flat_token_response() {
+        let json = r#"{
+            "code": 0,
+            "msg": "ok",
+            "tenant_access_token": "t-abc123",
+            "expire": 7200
+        }"#;
+        let resp: TenantAccessTokenResponse = serde_json::from_str(json).unwrap();
+        assert_eq!(resp.code, 0);
+        assert_eq!(resp.msg, "ok");
+        assert_eq!(resp.tenant_access_token, "t-abc123");
+        assert_eq!(resp.expire, 7200);
+    }
+
+    #[test]
+    fn parse_token_response_rejects_missing_token() {
+        let json = r#"{"code": 0, "msg": "ok", "expire": 7200}"#;
+        let result: Result<TenantAccessTokenResponse, _> = serde_json::from_str(json);
+        assert!(result.is_err(), "should fail when tenant_access_token is missing");
+    }
+
+    #[test]
+    fn parse_token_response_rejects_missing_expire() {
+        let json = r#"{"code": 0, "msg": "ok", "tenant_access_token": "t-abc"}"#;
+        let result: Result<TenantAccessTokenResponse, _> = serde_json::from_str(json);
+        assert!(result.is_err(), "should fail when expire is missing");
+    }
+
+    #[test]
+    fn parse_token_response_defaults_code_and_msg() {
+        let json = r#"{"tenant_access_token": "t-abc", "expire": 3600}"#;
+        let resp: TenantAccessTokenResponse = serde_json::from_str(json).unwrap();
+        assert_eq!(resp.code, 0);
+        assert_eq!(resp.msg, "");
+        assert_eq!(resp.tenant_access_token, "t-abc");
+        assert_eq!(resp.expire, 3600);
+    }
+
+    #[test]
+    fn parse_token_error_response() {
+        let json = r#"{
+            "code": 10003,
+            "msg": "invalid app_id",
+            "tenant_access_token": "",
+            "expire": 0
+        }"#;
+        let resp: TenantAccessTokenResponse = serde_json::from_str(json).unwrap();
+        assert_eq!(resp.code, 10003);
+        assert!(resp.tenant_access_token.is_empty());
+    }
+}
@@ -100,6 +100,14 @@ struct TelegramMessage {

    /// Sticker.
    sticker: Option<TelegramSticker>,
+
+    /// Forum topic ID. Present when the message is sent inside a forum topic.
+    #[serde(default)]
+    message_thread_id: Option<i64>,
+
+    /// True when this message is sent inside a forum topic.
+    #[serde(default)]
+    is_topic_message: Option<bool>,
 }

 /// Telegram PhotoSize object.
@@ -290,6 +298,10 @@ struct TelegramMessageMetadata {

    /// Whether this is a private (DM) chat.
    is_private: bool,
+
+    /// Forum topic thread ID (for routing replies back to the correct topic).
+    #[serde(default, skip_serializing_if = "Option::is_none")]
+    message_thread_id: Option<i64>,
 }

 /// Channel configuration injected by host.
@@ -348,6 +360,8 @@ enum TelegramStatusAction {
 }

 const TELEGRAM_STATUS_MAX_CHARS: usize = 600;
+/// Telegram's hard limit for message text length.
+const TELEGRAM_MAX_MESSAGE_LEN: usize = 4096;

 fn truncate_status_message(input: &str, max_chars: usize) -> String {
    let mut iter = input.chars();
@@ -359,6 +373,73 @@ fn truncate_status_message(input: &str, max_chars: usize) -> String {
    }
 }

+/// Split a long message into chunks that fit within Telegram's 4096-char limit.
+///
+/// Tries to split at the most natural boundary available (in priority order):
+/// 1. Double newline (paragraph break)
+/// 2. Single newline
+/// 3. Sentence end (`. `, `! `, `? `)
+/// 4. Word boundary (space)
+/// 5. Hard cut at the limit (last resort for pathological input)
+fn split_message(text: &str) -> Vec<String> {
+    if text.chars().count() <= TELEGRAM_MAX_MESSAGE_LEN {
+        return vec![text.to_string()];
+    }
+
+    let mut chunks: Vec<String> = Vec::new();
+    let mut remaining = text;
+
+    while !remaining.is_empty() {
+        // Count chars to find the byte offset for our window.
+        let window_bytes = remaining
+            .char_indices()
+            .take(TELEGRAM_MAX_MESSAGE_LEN)
+            .last()
+            .map(|(byte_idx, ch)| byte_idx + ch.len_utf8())
+            .unwrap_or(remaining.len());
+
+        if window_bytes >= remaining.len() {
+            // Remainder fits entirely.
+            chunks.push(remaining.to_string());
+            break;
+        }
+
+        let window = &remaining[..window_bytes];
+
+        // 1. Double newline — best paragraph boundary
+        let split_at = window.rfind("\n\n")
+            // 2. Single newline
+            .or_else(|| window.rfind('\n'))
+            // 3. Sentence-ending punctuation followed by space.
+            //    Note: this only detects ASCII punctuation (. ! ?), not CJK
+            //    sentence-ending marks (。！？). CJK text falls through to
+            //    word-boundary or hard-cut splitting.
+            .or_else(|| {
+                let bytes = window.as_bytes();
+                // Search backwards for '. ', '! ', '? '
+                (1..bytes.len()).rev().find(|&i| {
+                    matches!(bytes[i - 1], b'.' | b'!' | b'?') && bytes[i] == b' '
+                })
+            })
+            // 4. Word boundary (last space)
+            .or_else(|| window.rfind(' '))
+            // 5. Hard cut
+            .unwrap_or(window_bytes);
+
+        // Avoid empty chunks (e.g. text starting with \n\n).
+        let split_at = if split_at == 0 { window_bytes } else { split_at };
+
+        // Trim whitespace at chunk boundaries for clean Telegram display.
+        // Note: this drops leading/trailing spaces at split points, which is
+        // acceptable for chat messages but means the concatenation of chunks
+        // may not exactly equal the original text when split at spaces.
+        chunks.push(remaining[..split_at].trim_end().to_string());
+        remaining = remaining[split_at..].trim_start();
+    }
+
+    chunks
+}
+
 fn status_message_for_user(update: &StatusUpdate) -> Option<String> {
    let message = update.message.trim();
    if message.is_empty() {
@@ -491,8 +572,7 @@ impl Guest for TelegramChannel {

            // Delete any existing webhook before polling. Telegram returns success
            // when no webhook exists, so any error here (e.g. 401) means a bad token.
-            delete_webhook()
-                .map_err(|e| format!("Bot token validation failed: {}", e))?;
+            delete_webhook().map_err(|e| format!("Bot token validation failed: {}", e))?;
        }

        // Configure polling only if not in webhook mode
@@ -680,7 +760,12 @@ impl Guest for TelegramChannel {
        let metadata: TelegramMessageMetadata = serde_json::from_str(&response.metadata_json)
            .map_err(|e| format!("Failed to parse metadata: {}", e))?;

-        send_response(metadata.chat_id, &response, Some(metadata.message_id))
+        send_response(
+            metadata.chat_id,
+            &response,
+            Some(metadata.message_id),
+            metadata.message_thread_id,
+        )
    }

    fn on_broadcast(user_id: String, response: AgentResponse) -> Result<(), String> {
@@ -688,7 +773,7 @@ impl Guest for TelegramChannel {
            .parse()
            .map_err(|e| format!("Invalid chat_id '{}': {}", user_id, e))?;

-        send_response(chat_id, &response, None)
+        send_response(chat_id, &response, None, None)
    }

    fn on_status(update: StatusUpdate) {
@@ -712,11 +797,15 @@ impl Guest for TelegramChannel {
        match action {
            TelegramStatusAction::Typing => {
                // POST /sendChatAction with action "typing"
-                let payload = serde_json::json!({
+                let mut payload = serde_json::json!({
                    "chat_id": metadata.chat_id,
                    "action": "typing"
                });

+                if let Some(thread_id) = metadata.message_thread_id {
+                    payload["message_thread_id"] = serde_json::Value::Number(thread_id.into());
+                }
+
                let payload_bytes = match serde_json::to_vec(&payload) {
                    Ok(b) => b,
                    Err(_) => return,
@@ -743,9 +832,13 @@ impl Guest for TelegramChannel {
            }
            TelegramStatusAction::Notify(prompt) => {
                // Send user-visible status updates for actionable events.
-                if let Err(first_err) =
-                    send_message(metadata.chat_id, &prompt, Some(metadata.message_id), None)
-                {
+                if let Err(first_err) = send_message(
+                    metadata.chat_id,
+                    &prompt,
+                    Some(metadata.message_id),
+                    None,
+                    metadata.message_thread_id,
+                ) {
                    channel_host::log(
                        channel_host::LogLevel::Warn,
                        &format!(
@@ -754,7 +847,13 @@ impl Guest for TelegramChannel {
                        ),
                    );

-                    if let Err(retry_err) = send_message(metadata.chat_id, &prompt, None, None) {
+                    if let Err(retry_err) = send_message(
+                        metadata.chat_id,
+                        &prompt,
+                        None,
+                        None,
+                        metadata.message_thread_id,
+                    ) {
                        channel_host::log(
                            channel_host::LogLevel::Debug,
                            &format!(
@@ -797,6 +896,14 @@ impl std::fmt::Display for SendError {
    }
 }

+/// Normalize `message_thread_id` for outbound API calls.
+///
+/// Telegram rejects `sendMessage` and file-send methods when
+/// `message_thread_id = 1` (the "General" topic), so omit it in that case.
+fn normalize_thread_id(thread_id: Option<i64>) -> Option<i64> {
+    thread_id.filter(|&id| id != 1)
+}
+
 /// Send a message via the Telegram Bot API.
 ///
 /// Returns the sent message_id on success. When `parse_mode` is set and
@@ -807,7 +914,10 @@ fn send_message(
    text: &str,
    reply_to_message_id: Option<i64>,
    parse_mode: Option<&str>,
+    message_thread_id: Option<i64>,
 ) -> Result<i64, SendError> {
+    let message_thread_id = normalize_thread_id(message_thread_id);
+
    let mut payload = serde_json::json!({
        "chat_id": chat_id,
        "text": text,
@@ -821,6 +931,10 @@ fn send_message(
        payload["parse_mode"] = serde_json::Value::String(mode.to_string());
    }

+    if let Some(thread_id) = message_thread_id {
+        payload["message_thread_id"] = serde_json::Value::Number(thread_id.into());
+    }
+
    let payload_bytes = serde_json::to_vec(&payload)
        .map_err(|e| SendError::Other(format!("Failed to serialize payload: {}", e)))?;

@@ -911,19 +1025,20 @@ fn download_telegram_file(file_id: &str) -> Result<Vec<u8>, String> {
    );

    let headers = serde_json::json!({});
-    let result =
-        channel_host::http_request("GET", &get_file_url, &headers.to_string(), None, None);
+    let result = channel_host::http_request("GET", &get_file_url, &headers.to_string(), None, None);

    let response = result.map_err(|e| format!("getFile request failed: {}", e))?;

    if response.status != 200 {
        let body_str = String::from_utf8_lossy(&response.body);
-        return Err(format!("getFile returned {}: {}", response.status, body_str));
+        return Err(format!(
+            "getFile returned {}: {}",
+            response.status, body_str
+        ));
    }

-    let api_response: TelegramApiResponse<TelegramFile> =
-        serde_json::from_slice(&response.body)
-            .map_err(|e| format!("Failed to parse getFile response: {}", e))?;
+    let api_response: TelegramApiResponse<TelegramFile> = serde_json::from_slice(&response.body)
+        .map_err(|e| format!("Failed to parse getFile response: {}", e))?;

    if !api_response.ok {
        return Err(format!(
@@ -953,16 +1068,12 @@ fn download_telegram_file(file_id: &str) -> Result<Vec<u8>, String> {
        file_path
    );

-    let result =
-        channel_host::http_request("GET", &download_url, &headers.to_string(), None, None);
+    let result = channel_host::http_request("GET", &download_url, &headers.to_string(), None, None);

    let response = result.map_err(|e| format!("File download failed: {}", e))?;

    if response.status != 200 {
-        return Err(format!(
-            "File download returned status {}",
-            response.status
-        ));
+        return Err(format!("File download returned status {}", response.status));
    }

    // Post-download size guard: Telegram metadata file_size is optional,
@@ -1036,7 +1147,10 @@ fn send_photo(
    mime_type: &str,
    data: &[u8],
    reply_to_message_id: Option<i64>,
+    message_thread_id: Option<i64>,
 ) -> Result<(), String> {
+    let message_thread_id = normalize_thread_id(message_thread_id);
+
    if data.len() > MAX_PHOTO_SIZE {
        channel_host::log(
            channel_host::LogLevel::Info,
@@ -1046,7 +1160,14 @@ fn send_photo(
                data.len()
            ),
        );
-        return send_document(chat_id, filename, mime_type, data, reply_to_message_id);
+        return send_document(
+            chat_id,
+            filename,
+            mime_type,
+            data,
+            reply_to_message_id,
+            message_thread_id,
+        );
    }

    let boundary = format!("ironclaw-{}", channel_host::now_millis());
@@ -1054,7 +1175,20 @@ fn send_photo(

    write_multipart_field(&mut body, &boundary, "chat_id", &chat_id.to_string());
    if let Some(msg_id) = reply_to_message_id {
-        write_multipart_field(&mut body, &boundary, "reply_to_message_id", &msg_id.to_string());
+        write_multipart_field(
+            &mut body,
+            &boundary,
+            "reply_to_message_id",
+            &msg_id.to_string(),
+        );
+    }
+    if let Some(thread_id) = message_thread_id {
+        write_multipart_field(
+            &mut body,
+            &boundary,
+            "message_thread_id",
+            &thread_id.to_string(),
+        );
    }
    write_multipart_file(&mut body, &boundary, "photo", filename, mime_type, data);
    body.extend_from_slice(format!("--{}--\r\n", boundary).as_bytes());
@@ -1097,13 +1231,29 @@ fn send_document(
    mime_type: &str,
    data: &[u8],
    reply_to_message_id: Option<i64>,
+    message_thread_id: Option<i64>,
 ) -> Result<(), String> {
+    let message_thread_id = normalize_thread_id(message_thread_id);
+
    let boundary = format!("ironclaw-{}", channel_host::now_millis());
    let mut body = Vec::new();

    write_multipart_field(&mut body, &boundary, "chat_id", &chat_id.to_string());
    if let Some(msg_id) = reply_to_message_id {
-        write_multipart_field(&mut body, &boundary, "reply_to_message_id", &msg_id.to_string());
+        write_multipart_field(
+            &mut body,
+            &boundary,
+            "reply_to_message_id",
+            &msg_id.to_string(),
+        );
+    }
+    if let Some(thread_id) = message_thread_id {
+        write_multipart_field(
+            &mut body,
+            &boundary,
+            "message_thread_id",
+            &thread_id.to_string(),
+        );
    }
    write_multipart_file(&mut body, &boundary, "document", filename, mime_type, data);
    body.extend_from_slice(format!("--{}--\r\n", boundary).as_bytes());
@@ -1140,12 +1290,7 @@ fn send_document(
 }

 /// Image MIME types that Telegram's sendPhoto API supports.
-const PHOTO_MIME_TYPES: &[&str] = &[
-    "image/jpeg",
-    "image/png",
-    "image/gif",
-    "image/webp",
-];
+const PHOTO_MIME_TYPES: &[&str] = &["image/jpeg", "image/png", "image/gif", "image/webp"];

 /// Send a full agent response (attachments + text) to a chat.
 ///
@@ -1154,10 +1299,11 @@ fn send_response(
    chat_id: i64,
    response: &AgentResponse,
    reply_to_message_id: Option<i64>,
+    message_thread_id: Option<i64>,
 ) -> Result<(), String> {
    // Send attachments first (photos/documents)
    for attachment in &response.attachments {
-        send_attachment(chat_id, attachment, reply_to_message_id)?;
+        send_attachment(chat_id, attachment, reply_to_message_id, message_thread_id)?;
    }

    // Skip text if empty and we already sent attachments
@@ -1165,16 +1311,64 @@ fn send_response(
        return Ok(());
    }

-    // Try Markdown, fall back to plain text on parse errors
-    match send_message(chat_id, &response.content, reply_to_message_id, Some("Markdown")) {
-        Ok(_) => Ok(()),
-        Err(SendError::ParseEntities(_)) => {
-            send_message(chat_id, &response.content, reply_to_message_id, None)
-                .map(|_| ())
-                .map_err(|e| format!("Plain-text retry also failed: {}", e))
-        }
-        Err(e) => Err(e.to_string()),
+    // Split large messages into chunks that fit Telegram's limit.
+    let chunks = split_message(&response.content);
+    let total = chunks.len();
+
+    // The first chunk replies to the original message; subsequent chunks
+    // reply to the previously sent chunk so they form a visual thread.
+    let mut reply_to = reply_to_message_id;
+
+    for (i, chunk) in chunks.into_iter().enumerate() {
+        // Try Markdown, fall back to plain text on parse errors
+        let result = send_message(chat_id, &chunk, reply_to, Some("Markdown"), message_thread_id);
+
+        let msg_id = match result {
+            Ok(id) => {
+                channel_host::log(
+                    channel_host::LogLevel::Debug,
+                    &format!(
+                        "Sent message chunk {}/{} to chat {}: message_id={}",
+                        i + 1,
+                        total,
+                        chat_id,
+                        id,
+                    ),
+                );
+                id
+            }
+            Err(SendError::ParseEntities(detail)) => {
+                channel_host::log(
+                    channel_host::LogLevel::Warn,
+                    &format!(
+                        "Markdown parse failed on chunk {}/{} ({}), retrying as plain text",
+                        i + 1,
+                        total,
+                        detail
+                    ),
+                );
+                let id = send_message(chat_id, &chunk, reply_to, None, message_thread_id)
+                    .map_err(|e| format!("Plain-text retry also failed: {}", e))?;
+                channel_host::log(
+                    channel_host::LogLevel::Debug,
+                    &format!(
+                        "Sent plain-text chunk {}/{} to chat {}: message_id={}",
+                        i + 1,
+                        total,
+                        chat_id,
+                        id,
+                    ),
+                );
+                id
+            }
+            Err(e) => return Err(e.to_string()),
+        };
+
+        // Each subsequent chunk threads off the previous sent message.
+        reply_to = Some(msg_id);
    }
+
+    Ok(())
 }

 /// Send a single attachment, choosing sendPhoto or sendDocument based on MIME type.
@@ -1182,6 +1376,7 @@ fn send_attachment(
    chat_id: i64,
    attachment: &Attachment,
    reply_to_message_id: Option<i64>,
+    message_thread_id: Option<i64>,
 ) -> Result<(), String> {
    if PHOTO_MIME_TYPES.contains(&attachment.mime_type.as_str()) {
        send_photo(
@@ -1190,6 +1385,7 @@ fn send_attachment(
            &attachment.mime_type,
            &attachment.data,
            reply_to_message_id,
+            message_thread_id,
        )
    } else {
        send_document(
@@ -1198,6 +1394,7 @@ fn send_attachment(
            &attachment.mime_type,
            &attachment.data,
            reply_to_message_id,
+            message_thread_id,
        )
    }
 }
@@ -1337,7 +1534,10 @@ fn register_webhook(tunnel_url: &str, webhook_secret: Option<&str>) -> Result<()
    let context = if retried { " (after retry)" } else { "" };
    channel_host::log(
        channel_host::LogLevel::Info,
-        &format!("Webhook registered successfully{}: {}", context, webhook_url),
+        &format!(
+            "Webhook registered successfully{}: {}",
+            context, webhook_url
+        ),
    );

    Ok(())
@@ -1357,6 +1557,7 @@ fn send_pairing_reply(chat_id: i64, code: &str) -> Result<(), String> {
        ),
        None,
        Some("Markdown"),
+        None,
    )
    .map(|_| ())
    .map_err(|e| e.to_string())
@@ -1438,7 +1639,9 @@ fn extract_attachments(message: &TelegramMessage) -> Vec<InboundAttachment> {
    if let Some(ref doc) = message.document {
        attachments.push(make_inbound_attachment(
            doc.file_id.clone(),
-            doc.mime_type.clone().unwrap_or_else(|| "application/octet-stream".to_string()),
+            doc.mime_type
+                .clone()
+                .unwrap_or_else(|| "application/octet-stream".to_string()),
            doc.file_name.clone(),
            doc.file_size.map(|s| s as u64),
            Some(get_file_url(&doc.file_id)),
@@ -1451,7 +1654,10 @@ fn extract_attachments(message: &TelegramMessage) -> Vec<InboundAttachment> {
    if let Some(ref audio) = message.audio {
        attachments.push(make_inbound_attachment(
            audio.file_id.clone(),
-            audio.mime_type.clone().unwrap_or_else(|| "audio/mpeg".to_string()),
+            audio
+                .mime_type
+                .clone()
+                .unwrap_or_else(|| "audio/mpeg".to_string()),
            audio.file_name.clone(),
            audio.file_size.map(|s| s as u64),
            Some(get_file_url(&audio.file_id)),
@@ -1464,7 +1670,10 @@ fn extract_attachments(message: &TelegramMessage) -> Vec<InboundAttachment> {
    if let Some(ref video) = message.video {
        attachments.push(make_inbound_attachment(
            video.file_id.clone(),
-            video.mime_type.clone().unwrap_or_else(|| "video/mp4".to_string()),
+            video
+                .mime_type
+                .clone()
+                .unwrap_or_else(|| "video/mp4".to_string()),
            video.file_name.clone(),
            video.file_size.map(|s| s as u64),
            Some(get_file_url(&video.file_id)),
@@ -1689,25 +1898,14 @@ fn handle_message(message: TelegramMessage) {

    let is_private = message.chat.chat_type == "private";

-    // Owner validation: when owner_id is set, only that user can message
-    let owner_id_str = channel_host::workspace_read(OWNER_ID_PATH).filter(|s| !s.is_empty());
+    let owner_id = channel_host::workspace_read(OWNER_ID_PATH)
+        .filter(|s| !s.is_empty())
+        .and_then(|s| s.parse::<i64>().ok());
+    let is_owner = owner_id == Some(from.id);

-    if let Some(ref id_str) = owner_id_str {
-        if let Ok(owner_id) = id_str.parse::<i64>() {
-            if from.id != owner_id {
-                channel_host::log(
-                    channel_host::LogLevel::Debug,
-                    &format!(
-                        "Dropping message from non-owner user {} (owner: {})",
-                        from.id, owner_id
-                    ),
-                );
-                return;
-            }
-        }
-    } else {
-        // No owner_id: apply authorization based on dm_policy and allow_from
-        // This applies to both private and group chats when owner_id is null
+    if !is_owner {
+        // Non-owner senders remain guests. Apply authorization based on
+        // dm_policy / allow_from before letting them chat in their own scope.
        let dm_policy =
            channel_host::workspace_read(DM_POLICY_PATH).unwrap_or_else(|| "pairing".to_string());

@@ -1814,6 +2012,7 @@ fn handle_message(message: TelegramMessage) {
        message_id: message.message_id,
        user_id: from.id,
        is_private,
+        message_thread_id: message.message_thread_id,
    };

    let metadata_json = serde_json::to_string(&metadata).unwrap_or_else(|_| "{}".to_string());
@@ -1838,7 +2037,7 @@ fn handle_message(message: TelegramMessage) {
        user_id: from.id.to_string(),
        user_name: Some(user_name),
        content: content_to_emit,
-        thread_id: None, // Telegram doesn't have threads in the same way
+        thread_id: Some(message.chat.id.to_string()),
        metadata_json,
        attachments,
    });
@@ -1951,6 +2150,102 @@ export!(TelegramChannel);
 mod tests {
    use super::*;

+    #[test]
+    fn test_split_message_short() {
+        let text = "Hello, world!";
+        let chunks = split_message(text);
+        assert_eq!(chunks, vec![text]);
+    }
+
+    #[test]
+    fn test_split_message_paragraph_boundary() {
+        let para_a = "A".repeat(3000);
+        let para_b = "B".repeat(3000);
+        let text = format!("{}\n\n{}", para_a, para_b);
+        let chunks = split_message(&text);
+        assert_eq!(chunks.len(), 2);
+        assert_eq!(chunks[0], para_a);
+        assert_eq!(chunks[1], para_b);
+    }
+
+    #[test]
+    fn test_split_message_word_boundary() {
+        // Build a string well over the limit with no newlines.
+        let words: Vec<String> = (0..1000).map(|i| format!("word{:04}", i)).collect();
+        let text = words.join(" ");
+        assert!(text.len() > TELEGRAM_MAX_MESSAGE_LEN);
+        let chunks = split_message(&text);
+        assert!(chunks.len() > 1, "expected multiple chunks");
+        for chunk in &chunks {
+            assert!(chunk.chars().count() <= TELEGRAM_MAX_MESSAGE_LEN);
+        }
+        // Rejoined chunks must equal the original text exactly.
+        let rejoined = chunks.join(" ");
+        assert_eq!(rejoined, text);
+    }
+
+    #[test]
+    fn test_split_message_each_chunk_fits() {
+        // Stress-test: 20 000 chars of mixed text.
+        let text: String = (0..500)
+            .map(|i| format!("Sentence number {}. ", i))
+            .collect();
+        assert!(text.len() > TELEGRAM_MAX_MESSAGE_LEN);
+        let chunks = split_message(&text);
+        for chunk in &chunks {
+            assert!(chunk.chars().count() <= TELEGRAM_MAX_MESSAGE_LEN);
+        }
+    }
+
+    #[test]
+    fn test_split_message_sentence_boundary() {
+        // Build text that exceeds the limit, with sentence boundaries inside.
+        let sentence = "This is a test sentence. ";
+        let repeat_count = TELEGRAM_MAX_MESSAGE_LEN / sentence.len() + 5;
+        let text: String = sentence.repeat(repeat_count);
+        assert!(text.chars().count() > TELEGRAM_MAX_MESSAGE_LEN);
+
+        let chunks = split_message(&text);
+        assert!(chunks.len() > 1);
+        // First chunk should end at a sentence boundary (trimmed)
+        let first = &chunks[0];
+        assert!(
+            first.ends_with('.'),
+            "First chunk should end at a sentence boundary, got: ...{}",
+            &first[first.len().saturating_sub(20)..]
+        );
+    }
+
+    #[test]
+    fn test_split_message_hard_cut_no_spaces() {
+        // Pathological input: a single huge "word" with no spaces or newlines.
+        let text = "x".repeat(TELEGRAM_MAX_MESSAGE_LEN * 2 + 100);
+        let chunks = split_message(&text);
+        assert!(chunks.len() >= 2);
+        for chunk in &chunks {
+            assert!(chunk.chars().count() <= TELEGRAM_MAX_MESSAGE_LEN);
+        }
+        // Rejoined must preserve all characters
+        let rejoined: String = chunks.concat();
+        assert_eq!(rejoined, text);
+    }
+
+    #[test]
+    fn test_split_message_multibyte_chars() {
+        // Emoji are 4 bytes each. Ensure we don't panic or split mid-character.
+        let emoji = "\u{1F600}"; // 😀
+        let text: String = emoji.repeat(TELEGRAM_MAX_MESSAGE_LEN + 100);
+        assert!(text.chars().count() > TELEGRAM_MAX_MESSAGE_LEN);
+
+        let chunks = split_message(&text);
+        assert!(chunks.len() >= 2);
+        for chunk in &chunks {
+            assert!(chunk.chars().count() <= TELEGRAM_MAX_MESSAGE_LEN);
+            // Every char should be a complete emoji
+            assert!(chunk.chars().all(|c| c == '\u{1F600}'));
+        }
+    }
+
    #[test]
    fn test_clean_message_text() {
        // Without bot_username: strips any leading @mention
@@ -2438,7 +2733,11 @@ mod tests {
        assert_eq!(attachments[0].id, "large_id"); // Largest photo
        assert_eq!(attachments[0].mime_type, "image/jpeg");
        assert_eq!(attachments[0].size_bytes, Some(54321));
-        assert!(attachments[0].source_url.as_ref().unwrap().contains("large_id"));
+        assert!(attachments[0]
+            .source_url
+            .as_ref()
+            .unwrap()
+            .contains("large_id"));
    }

    #[test]
@@ -2490,9 +2789,7 @@ mod tests {
            attachments[0].filename.as_deref(),
            Some("voice_voice_xyz.ogg")
        );
-        assert!(attachments[0]
-            .extras_json
-            .contains("\"duration_secs\":5"));
+        assert!(attachments[0].extras_json.contains("\"duration_secs\":5"));
    }

    #[test]
@@ -2638,18 +2935,33 @@ mod tests {
        };

        // PDFs and Office docs should be downloaded
-        assert!(is_downloadable_document(&make("application/pdf", Some("report.pdf"))));
+        assert!(is_downloadable_document(&make(
+            "application/pdf",
+            Some("report.pdf")
+        )));
        assert!(is_downloadable_document(&make(
            "application/vnd.openxmlformats-officedocument.wordprocessingml.document",
            Some("doc.docx"),
        )));
-        assert!(is_downloadable_document(&make("text/plain", Some("notes.txt"))));
+        assert!(is_downloadable_document(&make(
+            "text/plain",
+            Some("notes.txt")
+        )));

        // Voice, image, audio, video should NOT be downloaded
-        assert!(!is_downloadable_document(&make("audio/ogg", Some("voice_123.ogg"))));
+        assert!(!is_downloadable_document(&make(
+            "audio/ogg",
+            Some("voice_123.ogg")
+        )));
        assert!(!is_downloadable_document(&make("image/jpeg", None)));
-        assert!(!is_downloadable_document(&make("audio/mpeg", Some("song.mp3"))));
-        assert!(!is_downloadable_document(&make("video/mp4", Some("clip.mp4"))));
+        assert!(!is_downloadable_document(&make(
+            "audio/mpeg",
+            Some("song.mp3")
+        )));
+        assert!(!is_downloadable_document(&make(
+            "video/mp4",
+            Some("clip.mp4")
+        )));
    }

    #[test]
@@ -2,9 +2,13 @@ coverage:
  status:
    project:
      default:
-        target: auto
-        threshold: 1%
+        target: 80%
+        threshold: 2%
    patch:
      default:
-        target: 80%
-        threshold: 5%
+        target: 90%
+
+comment:
+  layout: "reach,diff,flags"
+  behavior: default
+  require_changes: true
@@ -324,7 +324,7 @@ mod tests {
            let violations = policy.check(&payload);
            let elapsed = start.elapsed();
            assert!(
-                elapsed.as_millis() < 100,
+                elapsed.as_millis() < 500,
                "excessive_urls pattern took {}ms on 100KB near-miss",
                elapsed.as_millis()
            );
@@ -349,7 +349,7 @@ mod tests {
            let violations = policy.check(&payload);
            let elapsed = start.elapsed();
            assert!(
-                elapsed.as_millis() < 100,
+                elapsed.as_millis() < 500,
                "obfuscated_string pattern took {}ms on 100KB near-miss",
                elapsed.as_millis()
            );
@@ -370,7 +370,7 @@ mod tests {
            let _violations = policy.check(&payload);
            let elapsed = start.elapsed();
            assert!(
-                elapsed.as_millis() < 100,
+                elapsed.as_millis() < 500,
                "shell_injection pattern took {}ms on 100KB near-miss",
                elapsed.as_millis()
            );
@@ -387,7 +387,7 @@ mod tests {
            let _violations = policy.check(&payload);
            let elapsed = start.elapsed();
            assert!(
-                elapsed.as_millis() < 100,
+                elapsed.as_millis() < 500,
                "sql_pattern took {}ms on 100KB near-miss",
                elapsed.as_millis()
            );
@@ -405,7 +405,7 @@ mod tests {
            let _violations = policy.check(&payload);
            let elapsed = start.elapsed();
            assert!(
-                elapsed.as_millis() < 100,
+                elapsed.as_millis() < 500,
                "crypto_private_key pattern took {}ms on 100KB near-miss",
                elapsed.as_millis()
            );
@@ -423,7 +423,7 @@ mod tests {
            let _violations = policy.check(&payload);
            let elapsed = start.elapsed();
            assert!(
-                elapsed.as_millis() < 100,
+                elapsed.as_millis() < 500,
                "system_file_access pattern took {}ms on 100KB near-miss",
                elapsed.as_millis()
            );
@@ -441,7 +441,7 @@ mod tests {
            let _violations = policy.check(&payload);
            let elapsed = start.elapsed();
            assert!(
-                elapsed.as_millis() < 100,
+                elapsed.as_millis() < 500,
                "encoded_exploit pattern took {}ms on 100KB near-miss",
                elapsed.as_millis()
            );
@@ -623,7 +623,7 @@ mod tests {
            let combining_marks: Vec<char> =
                (0x0300u32..=0x0331).filter_map(char::from_u32).collect();
            assert!(combining_marks.len() >= 50);
-            let marks: String = combining_marks[..50].iter().collect(); // safety: Vec<char> slice, not byte slice
+            let marks: String = combining_marks[..50].iter().collect();
            let input = format!("prefix a{marks}suffix padding to reach minimum length for check");
            assert!(
                !has_excessive_repetition(&input),
@@ -15,7 +15,7 @@ configurations.
 | io.net | `ionet` | `IONET_API_KEY` | Intelligence API |
 | Mistral | `mistral` | `MISTRAL_API_KEY` | Mistral models |
 | Yandex AI Studio | `yandex` | `YANDEX_API_KEY` | YandexGPT models |
-| MiniMax | `minimax` | `MINIMAX_API_KEY` | MiniMax-M2.5 models |
+| MiniMax | `minimax` | `MINIMAX_API_KEY` | MiniMax-M2.7 models |
 | Cloudflare Workers AI | `cloudflare` | `CLOUDFLARE_API_KEY` | Access to Workers AI |
 | Ollama | `ollama` | No | Local inference |
 | AWS Bedrock | `bedrock` | AWS credentials | Native Converse API |
@@ -84,7 +84,7 @@ LLM_BACKEND=minimax
 MINIMAX_API_KEY=...
 ```

-Available models: `MiniMax-M2.5` (default), `MiniMax-M2.5-highspeed`
+Available models: `MiniMax-M2.7` (default), `MiniMax-M2.7-highspeed`, `MiniMax-M2.5`, `MiniMax-M2.5-highspeed`

 To use the China mainland endpoint, set:

@@ -1,24 +0,0 @@
-- Append-only audit log for security-relevant system events.
-- No UPDATE or DELETE should ever be issued on this table.
-
-CREATE TABLE IF NOT EXISTS audit_log (
-    id              BIGSERIAL PRIMARY KEY,
-    event_id        BIGINT NOT NULL,
-    event_type      VARCHAR(64) NOT NULL,
-    source_module   VARCHAR(64) NOT NULL,
-    source_component VARCHAR(64) NOT NULL,
-    category        VARCHAR(32) NOT NULL,
-    session_id      UUID,
-    thread_id       UUID,
-    job_id          UUID,
-    user_id         VARCHAR(255),
-    payload         JSONB NOT NULL DEFAULT '{}',
-    created_at      TIMESTAMPTZ NOT NULL DEFAULT NOW()
-);
-
-- Indexes for common query patterns
-CREATE INDEX IF NOT EXISTS idx_audit_log_created_at ON audit_log (created_at DESC);
-CREATE INDEX IF NOT EXISTS idx_audit_log_job_id ON audit_log (job_id) WHERE job_id IS NOT NULL;
-CREATE INDEX IF NOT EXISTS idx_audit_log_session_id ON audit_log (session_id) WHERE session_id IS NOT NULL;
-CREATE INDEX IF NOT EXISTS idx_audit_log_user_id ON audit_log (user_id) WHERE user_id IS NOT NULL;
-CREATE INDEX IF NOT EXISTS idx_audit_log_event_type ON audit_log (event_type);
@@ -0,0 +1,11 @@
+-- Remove the legacy 'default' sentinel from routine notifications.
+-- A NULL notify_user now means "resolve the configured owner's last-seen
+-- channel target at send time."
+
+ALTER TABLE routines
+    ALTER COLUMN notify_user DROP NOT NULL,
+    ALTER COLUMN notify_user DROP DEFAULT;
+
+UPDATE routines
+SET notify_user = NULL
+WHERE notify_user = 'default';
@@ -26,7 +26,7 @@ CREATE TABLE routines (

    -- Notification preferences
    notify_channel TEXT,                 -- NULL = use default
-    notify_user TEXT NOT NULL DEFAULT 'default',
+    notify_user TEXT,
    notify_on_success BOOLEAN NOT NULL DEFAULT false,
    notify_on_failure BOOLEAN NOT NULL DEFAULT true,
    notify_on_attention BOOLEAN NOT NULL DEFAULT true,
@@ -393,8 +393,8 @@
    "api_key_required": true,
    "base_url_env": "MINIMAX_BASE_URL",
    "model_env": "MINIMAX_MODEL",
-    "default_model": "MiniMax-M2.5",
-    "description": "MiniMax API (MiniMax-M2.5 and MiniMax-M2.5-highspeed models)",
+    "default_model": "MiniMax-M2.7",
+    "description": "MiniMax API (MiniMax-M2.7, MiniMax-M2.7-highspeed, MiniMax-M2.5 and MiniMax-M2.5-highspeed models)",
    "setup": {
      "kind": "api_key",
      "secret_name": "llm_minimax_api_key",
@@ -2,7 +2,7 @@
  "name": "discord",
  "display_name": "Discord Channel",
  "kind": "channel",
-  "version": "0.2.0",
+  "version": "0.2.1",
  "wit_version": "0.3.0",
  "description": "Talk to your agent in Discord",
  "keywords": [
@@ -18,8 +18,8 @@
  },
  "artifacts": {
    "wasm32-wasip2": {
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.18.0/discord-0.2.0-wasm32-wasip2.tar.gz",
-      "sha256": "efa1b9019fa33e243f8db1e1fcc732731d45836336bdd26ca19b6fe227ca8b69"
+      "url": "https://github.com/nearai/ironclaw/releases/download/v0.19.0/channel-discord-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "6159cb54aa44a9d8219e29bf0aea9404213b20ff567506fe75f23d4698d6ec18"
    }
  },
  "auth_summary": {
@@ -2,7 +2,7 @@
  "name": "feishu",
  "display_name": "Feishu / Lark Channel",
  "kind": "channel",
-  "version": "0.1.0",
+  "version": "0.1.2",
  "wit_version": "0.3.0",
  "description": "Talk to your agent through a Feishu or Lark bot",
  "keywords": [
@@ -17,7 +17,12 @@
    "capabilities": "feishu.capabilities.json",
    "crate_name": "feishu-channel"
  },
-  "artifacts": {},
+  "artifacts": {
+    "wasm32-wasip2": {
+      "sha256": "5fca74022264d1c8e78a0853766276f7ffa3cf0d8065b2f51ca10985acad4714",
+      "url": "https://github.com/nearai/ironclaw/releases/download/v0.19.0/channel-feishu-0.1.1-wasm32-wasip2.tar.gz"
+    }
+  },
  "auth_summary": {
    "method": "manual",
    "provider": "Feishu / Lark",
@@ -2,7 +2,7 @@
  "name": "telegram",
  "display_name": "Telegram Channel",
  "kind": "channel",
-  "version": "0.2.3",
+  "version": "0.2.5",
  "wit_version": "0.3.0",
  "description": "Talk to your agent through a Telegram bot",
  "keywords": [
@@ -18,8 +18,8 @@
  },
  "artifacts": {
    "wasm32-wasip2": {
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.18.0/telegram-0.2.3-wasm32-wasip2.tar.gz",
-      "sha256": "b9a83d5a2d1285ce0ec116b354336a1f245f893291ccb01dffbcaccf89d72aed"
+      "url": "https://github.com/nearai/ironclaw/releases/download/v0.20.0/channel-telegram-0.2.5-wasm32-wasip2.tar.gz",
+      "sha256": "1ef20a538f55b379e049356e4d6758006251846bc3365ceaa1c87eba8379a329"
    }
  },
  "auth_summary": {
@@ -2,7 +2,7 @@
  "name": "github",
  "display_name": "GitHub",
  "kind": "tool",
-  "version": "0.2.0",
+  "version": "0.2.1",
  "wit_version": "0.3.0",
  "description": "GitHub integration for issues, PRs, repos, and code search",
  "keywords": [
@@ -19,8 +19,8 @@
  },
  "artifacts": {
    "wasm32-wasip2": {
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.18.0/github-0.2.0-wasm32-wasip2.tar.gz",
-      "sha256": "da9fac56b6f20197a415489bbaec9fefb085a5cf6324cab79ea48a47eb19c13b"
+      "url": "https://github.com/nearai/ironclaw/releases/download/v0.19.0/tool-github-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "92c530b3ad172e2372d819744b5233f1d8f65768e26eb5a6c213eba3ce1de758"
    }
  },
  "auth_summary": {
@@ -21,8 +21,8 @@
  },
  "artifacts": {
    "wasm32-wasip2": {
-      "url": "https://github.com/nearai/ironclaw/releases/latest/download/llm-context-wasm32-wasip2.tar.gz",
-      "sha256": "581cc5867ef3b75116b7ddc8161e63dd92befe2b53e6ad8213c007639aa243c3"
+      "url": "https://github.com/nearai/ironclaw/releases/download/v0.19.0/tool-llm-context-0.1.0-wasm32-wasip2.tar.gz",
+      "sha256": "d9ced2b1226b879135891e0ee40e072c7c95412e1b2462925a23853e1f92497e"
    }
  },
  "auth_summary": {
@@ -17,8 +17,8 @@
  },
  "artifacts": {
    "wasm32-wasip2": {
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.18.0/slack-0.2.1-wasm32-wasip2.tar.gz",
-      "sha256": "d4667e35126986509d862bc3a0088777305d8f41c75de83c1e223b42312ede48"
+      "url": "https://github.com/nearai/ironclaw/releases/download/v0.19.0/tool-slack-0.2.0-wasm32-wasip2.tar.gz",
+      "sha256": "ccfb0415d7a04f9497726c712d15216de36e86f498b849101283c017f5ab4efb"
    }
  },
  "auth_summary": {
@@ -18,8 +18,8 @@
  },
  "artifacts": {
    "wasm32-wasip2": {
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.18.0/telegram-0.2.2-wasm32-wasip2.tar.gz",
-      "sha256": "b9a83d5a2d1285ce0ec116b354336a1f245f893291ccb01dffbcaccf89d72aed"
+      "url": "https://github.com/nearai/ironclaw/releases/download/v0.19.0/tool-telegram-0.2.0-wasm32-wasip2.tar.gz",
+      "sha256": "c17065ca41fae5f2a7c43b36144686718cd310a2f22442313bb1aa82bbad0ae4"
    }
  },
  "auth_summary": {
@@ -2,7 +2,7 @@
  "name": "web-search",
  "display_name": "Web Search",
  "kind": "tool",
-  "version": "0.2.0",
+  "version": "0.2.1",
  "wit_version": "0.3.0",
  "description": "Search the web using Brave Search API",
  "keywords": [
@@ -18,8 +18,8 @@
  },
  "artifacts": {
    "wasm32-wasip2": {
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.18.0/web-search-0.2.0-wasm32-wasip2.tar.gz",
-      "sha256": "56834573c54ea2a33cea1eb0f04bbdf59f1ef8d8702995cf431b0921302eeccc"
+      "url": "https://github.com/nearai/ironclaw/releases/download/v0.19.0/tool-web-search-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "bad275ca4ec314adea5241d6b92c44ccf9cebcbca8e30ba2493cc0bcb4b57218"
    }
  },
  "auth_summary": {
@@ -3,4 +3,5 @@ git_release_enable = false

 [[package]]
 name = "ironclaw_safety"
+publish = false
 release = false
@@ -134,11 +134,8 @@ fi
 #    Excludes test files, test modules, and debug_assert (compiled out in release).
 #    Suppress with "// safety: <reason>".
 PROD_DIFF="$DIFF_OUTPUT"
-# Strip all hunks from test-only files (tests/ directory, *_test.rs, test_*.rs, benches/)
-PROD_DIFF=$(echo "$PROD_DIFF" | awk '
-    /^diff --git/ { in_test_file = ($0 ~ /tests\/|_test\.rs|test_.*\.rs|benches\//) }
-    !in_test_file { print }
-' || true)
+# Strip hunks from test-only files (tests/ directory, *_test.rs, test_*.rs)
+PROD_DIFF=$(echo "$PROD_DIFF" | grep -v '^+++ b/tests/' || true)
 # Strip hunks whose @@ context line indicates a test module.
 # git diff includes the enclosing function/module name after @@.
 # Only match `mod tests` (the conventional #[cfg(test)] module) — do NOT
@@ -8,15 +8,21 @@ Replace `{{...}}` placeholders before use.
 {
  "name": "wf-issue-plan",
  "description": "Create implementation plan when a new issue arrives",
-  "trigger_type": "system_event",
-  "event_source": "github",
-  "event_type": "issue.opened",
-  "event_filters": {
-    "repository_name": "{{repository}}"
-  },
-  "action_type": "full_job",
  "prompt": "For issue #{{issue_number}} in {{repository}}, produce a concrete implementation plan with milestones, edge cases, and tests. Post/update an issue comment with the plan.",
-  "cooldown_secs": 30
+  "request": {
+    "kind": "system_event",
+    "source": "github",
+    "event_type": "issue.opened",
+    "filters": {
+      "repository_name": "{{repository}}"
+    }
+  },
+  "execution": {
+    "mode": "full_job"
+  },
+  "advanced": {
+    "cooldown_secs": 30
+  }
 }
 ```

@@ -28,16 +34,22 @@ Trigger per-maintainer by creating one routine per handle, or maintain a shared
 {
  "name": "wf-maintainer-comment-gate-{{maintainer}}",
  "description": "React to maintainer guidance comments on issues/PRs",
-  "trigger_type": "system_event",
-  "event_source": "github",
-  "event_type": "pr.comment.created",
-  "event_filters": {
-    "repository_name": "{{repository}}",
-    "comment_author": "{{maintainer}}"
-  },
-  "action_type": "full_job",
  "prompt": "Read the maintainer comment and decide: update plan or start/continue implementation. If plan changes are requested, edit the plan artifact first. If implementation is requested, continue on the feature branch and update PR status/comment.",
-  "cooldown_secs": 20
+  "request": {
+    "kind": "system_event",
+    "source": "github",
+    "event_type": "pr.comment.created",
+    "filters": {
+      "repository_name": "{{repository}}",
+      "comment_author": "{{maintainer}}"
+    }
+  },
+  "execution": {
+    "mode": "full_job"
+  },
+  "advanced": {
+    "cooldown_secs": 20
+  }
 }
 ```

@@ -47,15 +59,21 @@ Trigger per-maintainer by creating one routine per handle, or maintain a shared
 {
  "name": "wf-pr-monitor-loop",
  "description": "Keep PR healthy: address review comments and refresh branch",
-  "trigger_type": "system_event",
-  "event_source": "github",
-  "event_type": "pr.synchronize",
-  "event_filters": {
-    "repository_name": "{{repository}}"
-  },
-  "action_type": "full_job",
  "prompt": "For PR #{{pr_number}}, collect open review comments and unresolved threads, apply fixes, push branch updates, and summarize remaining blockers. If conflict with {{main_branch}}, rebase/merge from origin/{{main_branch}} and resolve safely.",
-  "cooldown_secs": 20
+  "request": {
+    "kind": "system_event",
+    "source": "github",
+    "event_type": "pr.synchronize",
+    "filters": {
+      "repository_name": "{{repository}}"
+    }
+  },
+  "execution": {
+    "mode": "full_job"
+  },
+  "advanced": {
+    "cooldown_secs": 20
+  }
 }
 ```

@@ -65,16 +83,22 @@ Trigger per-maintainer by creating one routine per handle, or maintain a shared
 {
  "name": "wf-ci-fix-loop",
  "description": "Fix failing CI checks on active PRs",
-  "trigger_type": "system_event",
-  "event_source": "github",
-  "event_type": "ci.check_run.completed",
-  "event_filters": {
-    "repository_name": "{{repository}}",
-    "ci_conclusion": "failure"
-  },
-  "action_type": "full_job",
  "prompt": "Find failing check details for PR #{{pr_number}}, implement minimal safe fixes, rerun or await CI, and post concise status updates. Prioritize deterministic and test-backed fixes.",
-  "cooldown_secs": 20
+  "request": {
+    "kind": "system_event",
+    "source": "github",
+    "event_type": "ci.check_run.completed",
+    "filters": {
+      "repository_name": "{{repository}}",
+      "ci_conclusion": "failure"
+    }
+  },
+  "execution": {
+    "mode": "full_job"
+  },
+  "advanced": {
+    "cooldown_secs": 20
+  }
 }
 ```

@@ -84,11 +108,17 @@ Trigger per-maintainer by creating one routine per handle, or maintain a shared
 {
  "name": "wf-staging-batch-review",
  "description": "Batch correctness review through staging, then merge to main",
-  "trigger_type": "cron",
-  "schedule": "0 0 */{{batch_interval_hours}} * * *",
-  "action_type": "full_job",
  "prompt": "Every cycle: list ready PRs, merge ready ones into {{staging_branch}}, run deep correctness analysis in batch, fix discovered issues on affected branches, ensure CI green, then merge {{staging_branch}} into {{main_branch}} if clean.",
-  "cooldown_secs": 120
+  "request": {
+    "kind": "cron",
+    "schedule": "0 0 */{{batch_interval_hours}} * * *"
+  },
+  "execution": {
+    "mode": "full_job"
+  },
+  "advanced": {
+    "cooldown_secs": 120
+  }
 }
 ```

@@ -98,16 +128,22 @@ Trigger per-maintainer by creating one routine per handle, or maintain a shared
 {
  "name": "wf-learning-memory",
  "description": "Capture merge learnings into shared memory",
-  "trigger_type": "system_event",
-  "event_source": "github",
-  "event_type": "pr.closed",
-  "event_filters": {
-    "repository_name": "{{repository}}",
-    "pr_merged": "true"
-  },
-  "action_type": "full_job",
  "prompt": "From merged PR #{{pr_number}}, extract preventable mistakes, reviewer themes, CI failure causes, and successful patterns. Write/update a shared memory doc with actionable rules to reduce cycle time and regressions.",
-  "cooldown_secs": 30
+  "request": {
+    "kind": "system_event",
+    "source": "github",
+    "event_type": "pr.closed",
+    "filters": {
+      "repository_name": "{{repository}}",
+      "pr_merged": "true"
+    }
+  },
+  "execution": {
+    "mode": "full_job"
+  },
+  "advanced": {
+    "cooldown_secs": 30
+  }
 }
 ```

@@ -115,7 +151,7 @@ Trigger per-maintainer by creating one routine per handle, or maintain a shared

 ```json
 {
-  "source": "github",
+  "event_source": "github",
  "event_type": "issue.opened",
  "payload": {
    "repository_name": "{{repository}}",
@@ -22,7 +22,7 @@ use crate::channels::{ChannelManager, IncomingMessage, OutgoingResponse};
 use crate::config::{AgentConfig, HeartbeatConfig, RoutineConfig, SkillsConfig};
 use crate::context::ContextManager;
 use crate::db::Database;
-use crate::error::Error;
+use crate::error::{ChannelError, Error};
 use crate::extensions::ExtensionManager;
 use crate::hooks::HookRegistry;
 use crate::llm::LlmProvider;
@@ -54,10 +54,75 @@ pub(crate) fn truncate_for_preview(output: &str, max_chars: usize) -> String {
    }
 }

+#[cfg(test)]
+fn resolve_routine_notification_user(metadata: &serde_json::Value) -> Option<String> {
+    resolve_owner_scope_notification_user(
+        metadata.get("notify_user").and_then(|value| value.as_str()),
+        metadata.get("owner_id").and_then(|value| value.as_str()),
+    )
+}
+
+fn trimmed_option(value: Option<&str>) -> Option<String> {
+    value
+        .map(str::trim)
+        .filter(|value| !value.is_empty())
+        .map(ToOwned::to_owned)
+}
+
+fn resolve_owner_scope_notification_user(
+    explicit_user: Option<&str>,
+    owner_fallback: Option<&str>,
+) -> Option<String> {
+    trimmed_option(explicit_user).or_else(|| trimmed_option(owner_fallback))
+}
+
+async fn resolve_channel_notification_user(
+    extension_manager: Option<&Arc<ExtensionManager>>,
+    channel: Option<&str>,
+    explicit_user: Option<&str>,
+    owner_fallback: Option<&str>,
+) -> Option<String> {
+    if let Some(user) = trimmed_option(explicit_user) {
+        return Some(user);
+    }
+
+    if let Some(channel_name) = trimmed_option(channel)
+        && let Some(extension_manager) = extension_manager
+        && let Some(target) = extension_manager
+            .notification_target_for_channel(&channel_name)
+            .await
+    {
+        return Some(target);
+    }
+
+    resolve_owner_scope_notification_user(explicit_user, owner_fallback)
+}
+
+async fn resolve_routine_notification_target(
+    extension_manager: Option<&Arc<ExtensionManager>>,
+    metadata: &serde_json::Value,
+) -> Option<String> {
+    resolve_channel_notification_user(
+        extension_manager,
+        metadata
+            .get("notify_channel")
+            .and_then(|value| value.as_str()),
+        metadata.get("notify_user").and_then(|value| value.as_str()),
+        metadata.get("owner_id").and_then(|value| value.as_str()),
+    )
+    .await
+}
+
+fn should_fallback_routine_notification(error: &ChannelError) -> bool {
+    !matches!(error, ChannelError::MissingRoutingTarget { .. })
+}
+
 /// Core dependencies for the agent.
 ///
 /// Bundles the shared components to reduce argument count.
 pub struct AgentDeps {
+    /// Resolved durable owner scope for the instance.
+    pub owner_id: String,
    pub store: Option<Arc<dyn Database>>,
    pub llm: Arc<dyn LlmProvider>,
    /// Cheap/fast LLM for lightweight tasks (heartbeat, routing, evaluation).
@@ -74,15 +139,15 @@ pub struct AgentDeps {
    /// Cost enforcement guardrails (daily budget, hourly rate limits).
    pub cost_guard: Arc<crate::agent::cost_guard::CostGuard>,
    /// SSE broadcast sender for live job event streaming to the web gateway.
-    pub sse_tx: Option<tokio::sync::broadcast::Sender<crate::events::DomainEvent>>,
-    /// Unified event bus. Optional for backward compatibility with tests.
-    pub event_bus: Option<crate::event_bus::EventBus>,
+    pub sse_tx: Option<tokio::sync::broadcast::Sender<crate::channels::web::types::SseEvent>>,
    /// HTTP interceptor for trace recording/replay.
    pub http_interceptor: Option<Arc<dyn crate::llm::recording::HttpInterceptor>>,
    /// Audio transcription middleware for voice messages.
    pub transcription: Option<Arc<crate::transcription::TranscriptionMiddleware>>,
    /// Document text extraction middleware for PDF, DOCX, PPTX, etc.
    pub document_extraction: Option<Arc<crate::document_extraction::DocumentExtractionMiddleware>>,
+    /// Software builder for self-repair tool rebuilding.
+    pub builder: Option<Arc<dyn crate::tools::SoftwareBuilder>>,
 }

 /// The main agent that coordinates all components.
@@ -98,12 +163,25 @@ pub struct Agent {
    pub(super) heartbeat_config: Option<HeartbeatConfig>,
    pub(super) hygiene_config: Option<crate::config::HygieneConfig>,
    pub(super) routine_config: Option<RoutineConfig>,
-    /// Optional slot to expose the routine engine to the gateway for manual triggering.
+    /// Shared routine-engine slot used for internal event matching and for exposing
+    /// the engine to gateway/manual trigger entry points.
    pub(super) routine_engine_slot:
-        Option<Arc<tokio::sync::RwLock<Option<Arc<crate::agent::routine_engine::RoutineEngine>>>>>,
+        Arc<tokio::sync::RwLock<Option<Arc<crate::agent::routine_engine::RoutineEngine>>>>,
 }

 impl Agent {
+    pub(super) fn owner_id(&self) -> &str {
+        if let Some(workspace) = self.deps.workspace.as_ref() {
+            debug_assert_eq!(
+                workspace.user_id(),
+                self.deps.owner_id,
+                "workspace.user_id() must stay aligned with deps.owner_id"
+            );
+        }
+
+        &self.deps.owner_id
+    }
+
    /// Create a new agent.
    ///
    /// Optionally accepts pre-created `ContextManager` and `SessionManager` for sharing
@@ -153,16 +231,21 @@ impl Agent {
            heartbeat_config,
            hygiene_config,
            routine_config,
-            routine_engine_slot: None,
+            routine_engine_slot: Arc::new(tokio::sync::RwLock::new(None)),
        }
    }

-    /// Set the routine engine slot for exposing the engine to the gateway.
+    /// Replace the routine-engine slot with a shared one so the gateway and
+    /// agent reference the same engine.
    pub fn set_routine_engine_slot(
        &mut self,
        slot: Arc<tokio::sync::RwLock<Option<Arc<crate::agent::routine_engine::RoutineEngine>>>>,
    ) {
-        self.routine_engine_slot = Some(slot);
+        self.routine_engine_slot = slot;
+    }
+
+    async fn routine_engine(&self) -> Option<Arc<crate::agent::routine_engine::RoutineEngine>> {
+        self.routine_engine_slot.read().await.clone()
    }

    // Convenience accessors
@@ -259,13 +342,21 @@ impl Agent {
        let mut message_stream = self.channels.start_all().await?;

        // Start self-repair task with notification forwarding
-        let repair = Arc::new(DefaultSelfRepair::new(
+        let mut self_repair = DefaultSelfRepair::new(
            self.context_manager.clone(),
            self.config.stuck_threshold,
            self.config.max_repair_attempts,
-        ));
+        );
+        if let Some(ref store) = self.deps.store {
+            self_repair = self_repair.with_store(Arc::clone(store));
+        }
+        if let Some(ref builder) = self.deps.builder {
+            self_repair = self_repair.with_builder(Arc::clone(builder), Arc::clone(self.tools()));
+        }
+        let repair = Arc::new(self_repair);
        let repair_interval = self.config.repair_check_interval;
        let repair_channels = self.channels.clone();
+        let repair_owner_id = self.owner_id().to_string();
        let repair_handle = tokio::spawn(async move {
            loop {
                tokio::time::sleep(repair_interval).await;
@@ -313,7 +404,9 @@ impl Agent {

                    if let Some(msg) = notification {
                        let response = OutgoingResponse::text(format!("Self-Repair: {}", msg));
-                        let _ = repair_channels.broadcast_all("default", response).await;
+                        let _ = repair_channels
+                            .broadcast_all(&repair_owner_id, response)
+                            .await;
                    }
                }

@@ -327,7 +420,9 @@ impl Agent {
                                "Self-Repair: Tool '{}' repaired: {}",
                                tool.name, message
                            ));
-                            let _ = repair_channels.broadcast_all("default", response).await;
+                            let _ = repair_channels
+                                .broadcast_all(&repair_owner_id, response)
+                                .await;
                        }
                        Ok(result) => {
                            tracing::info!("Tool repair result: {:?}", result);
@@ -364,8 +459,12 @@ impl Agent {
                        .timezone
                        .clone()
                        .or_else(|| Some(self.config.default_timezone.clone()));
-                    if let (Some(user), Some(channel)) =
-                        (&hb_config.notify_user, &hb_config.notify_channel)
+                    let heartbeat_notify_user = resolve_owner_scope_notification_user(
+                        hb_config.notify_user.as_deref(),
+                        Some(self.owner_id()),
+                    );
+                    if let Some(channel) = &hb_config.notify_channel
+                        && let Some(user) = heartbeat_notify_user.as_deref()
                    {
                        config = config.with_notify(user, channel);
                    }
@@ -376,15 +475,22 @@ impl Agent {

                    // Spawn notification forwarder that routes through channel manager
                    let notify_channel = hb_config.notify_channel.clone();
-                    let notify_user = hb_config.notify_user.clone();
+                    let notify_target = resolve_channel_notification_user(
+                        self.deps.extension_manager.as_ref(),
+                        hb_config.notify_channel.as_deref(),
+                        hb_config.notify_user.as_deref(),
+                        Some(self.owner_id()),
+                    )
+                    .await;
+                    let notify_user = heartbeat_notify_user;
                    let channels = self.channels.clone();
                    tokio::spawn(async move {
                        while let Some(response) = notify_rx.recv().await {
-                            let user = notify_user.as_deref().unwrap_or("default");
-
                            // Try the configured channel first, fall back to
                            // broadcasting on all channels.
-                            let targeted_ok = if let Some(ref channel) = notify_channel {
+                            let targeted_ok = if let Some(ref channel) = notify_channel
+                                && let Some(ref user) = notify_target
+                            {
                                channels
                                    .broadcast(channel, user, response.clone())
                                    .await
@@ -393,7 +499,7 @@ impl Agent {
                                false
                            };

-                            if !targeted_ok {
+                            if !targeted_ok && let Some(ref user) = notify_user {
                                let results = channels.broadcast_all(user, response).await;
                                for (ch, result) in results {
                                    if let Err(e) = result {
@@ -462,32 +568,60 @@ impl Agent {

                    // Spawn notification forwarder (mirrors heartbeat pattern)
                    let channels = self.channels.clone();
+                    let extension_manager = self.deps.extension_manager.clone();
                    tokio::spawn(async move {
                        while let Some(response) = notify_rx.recv().await {
-                            let user = response
-                                .metadata
-                                .get("notify_user")
-                                .and_then(|v| v.as_str())
-                                .unwrap_or("default")
-                                .to_string();
                            let notify_channel = response
                                .metadata
                                .get("notify_channel")
                                .and_then(|v| v.as_str())
                                .map(|s| s.to_string());
+                            let fallback_user = resolve_owner_scope_notification_user(
+                                response
+                                    .metadata
+                                    .get("notify_user")
+                                    .and_then(|v| v.as_str()),
+                                response.metadata.get("owner_id").and_then(|v| v.as_str()),
+                            );
+                            let Some(user) = resolve_routine_notification_target(
+                                extension_manager.as_ref(),
+                                &response.metadata,
+                            )
+                            .await
+                            else {
+                                tracing::warn!(
+                                    notify_channel = ?notify_channel,
+                                    "Skipping routine notification with no explicit target or owner scope"
+                                );
+                                continue;
+                            };

                            // Try the configured channel first, fall back to
                            // broadcasting on all channels.
                            let targeted_ok = if let Some(ref channel) = notify_channel {
-                                channels
-                                    .broadcast(channel, &user, response.clone())
-                                    .await
-                                    .is_ok()
+                                match channels.broadcast(channel, &user, response.clone()).await {
+                                    Ok(()) => true,
+                                    Err(e) => {
+                                        let should_fallback =
+                                            should_fallback_routine_notification(&e);
+                                        tracing::warn!(
+                                            channel = %channel,
+                                            user = %user,
+                                            error = %e,
+                                            should_fallback,
+                                            "Failed to send routine notification to configured channel"
+                                        );
+                                        if !should_fallback {
+                                            continue;
+                                        }
+                                        false
+                                    }
+                                }
                            } else {
                                false
                            };

-                            if !targeted_ok {
+                            if !targeted_ok && let Some(user) = fallback_user {
                                let results = channels.broadcast_all(&user, response).await;
                                for (ch, result) in results {
                                    if let Err(e) = result {
@@ -514,9 +648,7 @@ impl Agent {
                    // via a local to use in the message loop below.

                    // Expose engine to gateway for manual triggering
-                    if let Some(ref slot) = self.routine_engine_slot {
-                        *slot.write().await = Some(Arc::clone(&engine));
-                    }
+                    *self.routine_engine_slot.write().await = Some(Arc::clone(&engine));

                    tracing::debug!(
                        "Routines enabled: cron ticker every {}s, max {} concurrent",
@@ -536,9 +668,6 @@ impl Agent {
            None
        };

-        // Extract engine ref for use in message loop
-        let routine_engine_for_loop = routine_handle.as_ref().map(|(_, e)| Arc::clone(e));
-
        // Main message loop
        tracing::debug!("Agent {} ready and listening", self.config.name);

@@ -646,14 +775,6 @@ impl Agent {
                    }
                }
            }
-
-            // Check event triggers (cheap in-memory regex, fires async if matched)
-            if let Some(ref engine) = routine_engine_for_loop {
-                let fired = engine.check_event_triggers(&message).await;
-                if fired > 0 {
-                    tracing::debug!("Fired {} event-triggered routines", fired);
-                }
-            }
        }

        // Cleanup
@@ -770,10 +891,7 @@ impl Agent {
        // For Signal, use signal_target from metadata (group:ID or phone number),
        // otherwise fall back to user_id
        let target = message
-            .metadata
-            .get("signal_target")
-            .and_then(|v| v.as_str())
-            .map(|s| s.to_string())
+            .routing_target()
            .unwrap_or_else(|| message.user_id.clone());
        self.tools()
            .set_message_tool_context(Some(message.channel.clone()), Some(target))
@@ -813,7 +931,7 @@ impl Agent {
        }

        // Hydrate thread from DB if it's a historical thread not in memory
-        if let Some(ref external_thread_id) = message.thread_id {
+        if let Some(external_thread_id) = message.conversation_scope() {
            tracing::trace!(
                message_id = %message.id,
                thread_id = %external_thread_id,
@@ -834,7 +952,7 @@ impl Agent {
            .resolve_thread(
                &message.user_id,
                &message.channel,
-                message.thread_id.as_deref(),
+                message.conversation_scope(),
            )
            .await;
        tracing::debug!(
@@ -901,6 +1019,24 @@ impl Agent {
            message.content.len()
        );

+        if !message.is_internal
+            && let Submission::UserInput { ref content } = submission
+            && let Some(engine) = self.routine_engine().await
+        {
+            let fired = engine
+                .check_event_triggers(&message.user_id, &message.channel, content)
+                .await;
+            if fired > 0 {
+                tracing::debug!(
+                    channel = %message.channel,
+                    user = %message.user_id,
+                    fired,
+                    "Consumed inbound user message with matching event-triggered routine(s)"
+                );
+                return Ok(Some(String::new()));
+            }
+        }
+
        // Process based on submission type
        let result = match submission {
            Submission::UserInput { content } => {
@@ -987,7 +1123,11 @@ impl Agent {

 #[cfg(test)]
 mod tests {
-    use super::truncate_for_preview;
+    use super::{
+        resolve_routine_notification_user, should_fallback_routine_notification,
+        truncate_for_preview,
+    };
+    use crate::error::ChannelError;

    #[test]
    fn test_truncate_short_input() {
@@ -1050,4 +1190,55 @@ mod tests {
        // 'h','e','l','l','o',' ','世','界' = 8 chars
        assert_eq!(result, "hello 世界...");
    }
+
+    #[test]
+    fn resolve_routine_notification_user_prefers_explicit_target() {
+        let metadata = serde_json::json!({
+            "notify_user": "12345",
+            "owner_id": "owner-scope",
+        });
+
+        let resolved = resolve_routine_notification_user(&metadata);
+        assert_eq!(resolved.as_deref(), Some("12345")); // safety: test-only assertion
+    }
+
+    #[test]
+    fn resolve_routine_notification_user_falls_back_to_owner_scope() {
+        let metadata = serde_json::json!({
+            "notify_user": null,
+            "owner_id": "owner-scope",
+        });
+
+        let resolved = resolve_routine_notification_user(&metadata);
+        assert_eq!(resolved.as_deref(), Some("owner-scope")); // safety: test-only assertion
+    }
+
+    #[test]
+    fn resolve_routine_notification_user_rejects_missing_values() {
+        let metadata = serde_json::json!({
+            "notify_user": "   ",
+        });
+
+        assert_eq!(resolve_routine_notification_user(&metadata), None); // safety: test-only assertion
+    }
+
+    #[test]
+    fn targeted_routine_notifications_do_not_fallback_without_owner_route() {
+        let error = ChannelError::MissingRoutingTarget {
+            name: "telegram".to_string(),
+            reason: "No stored owner routing target for channel 'telegram'.".to_string(),
+        };
+
+        assert!(!should_fallback_routine_notification(&error)); // safety: test-only assertion
+    }
+
+    #[test]
+    fn targeted_routine_notifications_may_fallback_for_other_errors() {
+        let error = ChannelError::SendFailed {
+            name: "telegram".to_string(),
+            reason: "timeout talking to channel".to_string(),
+        };
+
+        assert!(should_fallback_routine_notification(&error)); // safety: test-only assertion
+    }
 }
@@ -836,7 +836,10 @@ impl Agent {
        // 1. Persist to DB if available.
        if let Some(store) = self.store() {
            let value = serde_json::Value::String(model.to_string());
-            if let Err(e) = store.set_setting("default", "selected_model", &value).await {
+            if let Err(e) = store
+                .set_setting(self.owner_id(), "selected_model", &value)
+                .await
+            {
                tracing::warn!("Failed to persist model to DB: {}", e);
            }
        }
@@ -29,7 +29,7 @@ pub(super) enum AgenticLoopResult {
    /// A tool requires approval before continuing.
    NeedApproval {
        /// The pending approval request to store.
-        pending: PendingApproval,
+        pending: Box<PendingApproval>,
    },
 }

@@ -140,13 +140,15 @@ impl Agent {

        // Create a JobContext for tool execution (chat doesn't have a real job)
        let mut job_ctx =
-            JobContext::with_user(&message.user_id, "chat", "Interactive chat session");
+            JobContext::with_user(&message.user_id, "chat", "Interactive chat session")
+                .with_requester_id(&message.sender_id);
        job_ctx.http_interceptor = self.deps.http_interceptor.clone();
        job_ctx.user_timezone = user_tz.name().to_string();
        job_ctx.metadata = serde_json::json!({
            "notify_channel": message.channel,
            "notify_user": message.user_id,
            "notify_thread_id": message.thread_id,
+            "notify_metadata": message.metadata,
        });

        // Build system prompts once for this turn. Two variants: with tools
@@ -215,9 +217,7 @@ impl Agent {
                reason: format!("Exceeded maximum tool iterations ({max_tool_iterations})"),
            }
            .into()),
-            LoopOutcome::NeedApproval(pending) => {
-                Ok(AgenticLoopResult::NeedApproval { pending: *pending })
-            }
+            LoopOutcome::NeedApproval(pending) => Ok(AgenticLoopResult::NeedApproval { pending }),
        }
    }

@@ -257,7 +257,7 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
    async fn check_signals(&self) -> LoopSignal {
        let sess = self.session.lock().await;
        if let Some(thread) = sess.threads.get(&self.thread_id)
-            && thread.state() == ThreadState::Interrupted
+            && thread.state == ThreadState::Interrupted
        {
            return LoopSignal::Stop;
        }
@@ -480,6 +480,7 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
            usize,
            crate::llm::ToolCall,
            Arc<dyn crate::tools::Tool>,
+            bool, // allow_always
        )> = None;

        for (idx, original_tc) in tool_calls.iter().enumerate() {
@@ -549,7 +550,8 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
                && let Some(tool) = tool_opt
            {
                use crate::tools::ApprovalRequirement;
-                let needs_approval = match tool.requires_approval(&tc.arguments) {
+                let requirement = tool.requires_approval(&tc.arguments);
+                let needs_approval = match requirement {
                    ApprovalRequirement::Never => false,
                    ApprovalRequirement::UnlessAutoApproved => {
                        let sess = self.session.lock().await;
@@ -584,7 +586,8 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
                        continue;
                    }

-                    approval_needed = Some((idx, tc, tool));
+                    let allow_always = !matches!(requirement, ApprovalRequirement::Always);
+                    approval_needed = Some((idx, tc, tool, allow_always));
                    break;
                }
            }
@@ -885,7 +888,7 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
        }

        // Handle approval if a tool needed it
-        if let Some((approval_idx, tc, tool)) = approval_needed {
+        if let Some((approval_idx, tc, tool, allow_always)) = approval_needed {
            let display_params = redact_params(&tc.arguments, tool.sensitive_params());
            let pending = PendingApproval {
                request_id: Uuid::new_v4(),
@@ -897,6 +900,7 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
                context_messages: reason_ctx.messages.clone(),
                deferred_tool_calls: tool_calls[approval_idx + 1..].to_vec(),
                user_timezone: Some(self.user_tz.name().to_string()),
+                allow_always,
            };

            return Ok(Some(LoopOutcome::NeedApproval(Box::new(pending))));
@@ -1175,6 +1179,7 @@ mod tests {
    /// Build a minimal `Agent` for unit testing (no DB, no workspace, no extensions).
    fn make_test_agent() -> Agent {
        let deps = AgentDeps {
+            owner_id: "default".to_string(),
            store: None,
            llm: Arc::new(StaticLlmProvider),
            cheap_llm: None,
@@ -1194,7 +1199,7 @@ mod tests {
            http_interceptor: None,
            transcription: None,
            document_extraction: None,
-            event_bus: None,
+            builder: None,
        };

        Agent::new(
@@ -1362,6 +1367,35 @@ mod tests {
        assert!(always_needs, "Always must always require approval");
    }

+    /// Regression test: `allow_always` must be `false` for `Always` and
+    /// `true` for `UnlessAutoApproved`, so the UI hides the "always" button
+    /// for tools that truly cannot be auto-approved.
+    #[test]
+    fn test_allow_always_matches_approval_requirement() {
+        use crate::tools::ApprovalRequirement;
+
+        // Mirrors the expression used in dispatcher.rs and thread_ops.rs:
+        //   let allow_always = !matches!(requirement, ApprovalRequirement::Always);
+
+        // UnlessAutoApproved → allow_always = true
+        let req = ApprovalRequirement::UnlessAutoApproved;
+        let allow_always = !matches!(req, ApprovalRequirement::Always);
+        assert!(
+            allow_always,
+            "UnlessAutoApproved should set allow_always = true"
+        );
+
+        // Always → allow_always = false
+        let req = ApprovalRequirement::Always;
+        let allow_always = !matches!(req, ApprovalRequirement::Always);
+        assert!(!allow_always, "Always should set allow_always = false");
+
+        // Never → allow_always = true (approval is never needed, but if it were, always would be ok)
+        let req = ApprovalRequirement::Never;
+        let allow_always = !matches!(req, ApprovalRequirement::Always);
+        assert!(allow_always, "Never should set allow_always = true");
+    }
+
    #[test]
    fn test_pending_approval_serialization_backcompat_without_deferred_calls() {
        // PendingApproval from before the deferred_tool_calls field was added
@@ -1407,6 +1441,7 @@ mod tests {
                },
            ],
            user_timezone: None,
+            allow_always: true,
        };

        let json = serde_json::to_string(&pending).expect("serialize");
@@ -2015,6 +2050,7 @@ mod tests {
    /// `max_tool_iterations` override.
    fn make_test_agent_with_llm(llm: Arc<dyn LlmProvider>, max_tool_iterations: usize) -> Agent {
        let deps = AgentDeps {
+            owner_id: "default".to_string(),
            store: None,
            llm,
            cheap_llm: None,
@@ -2034,7 +2070,7 @@ mod tests {
            http_interceptor: None,
            transcription: None,
            document_extraction: None,
-            event_bus: None,
+            builder: None,
        };

        Agent::new(
@@ -2129,6 +2165,7 @@ mod tests {
        let max_iter = 3;
        let agent = {
            let deps = AgentDeps {
+                owner_id: "default".to_string(),
                store: None,
                llm,
                cheap_llm: None,
@@ -2152,7 +2189,7 @@ mod tests {
                http_interceptor: None,
                transcription: None,
                document_extraction: None,
-                event_bus: None,
+                builder: None,
            };

            Agent::new(
@@ -26,6 +26,8 @@
 use std::sync::Arc;
 use std::time::Duration;

+use chrono::TimeZone as _;
+use chrono_tz::Tz;
 use tokio::sync::mpsc;

 use crate::channels::OutgoingResponse;
@@ -37,7 +39,7 @@ use crate::workspace::hygiene::HygieneConfig;
 /// Configuration for the heartbeat runner.
 #[derive(Debug, Clone)]
 pub struct HeartbeatConfig {
-    /// Interval between heartbeat checks.
+    /// Interval between heartbeat checks (used when fire_at is not set).
    pub interval: Duration,
    /// Whether heartbeat is enabled.
    pub enabled: bool,
@@ -47,11 +49,13 @@ pub struct HeartbeatConfig {
    pub notify_user_id: Option<String>,
    /// Channel to notify on heartbeat findings.
    pub notify_channel: Option<String>,
+    /// Fixed time-of-day to fire (24h). When set, interval is ignored.
+    pub fire_at: Option<chrono::NaiveTime>,
    /// Hour (0-23) when quiet hours start.
    pub quiet_hours_start: Option<u32>,
    /// Hour (0-23) when quiet hours end.
    pub quiet_hours_end: Option<u32>,
-    /// Timezone for quiet hours evaluation (IANA name).
+    /// Timezone for fire_at and quiet hours evaluation (IANA name).
    pub timezone: Option<String>,
 }

@@ -63,6 +67,7 @@ impl Default for HeartbeatConfig {
            max_failures: 3,
            notify_user_id: None,
            notify_channel: None,
+            fire_at: None,
            quiet_hours_start: None,
            quiet_hours_end: None,
            timezone: None,
@@ -109,6 +114,21 @@ impl HeartbeatConfig {
        self.notify_channel = Some(channel.into());
        self
    }
+
+    /// Set a fixed time-of-day to fire (overrides interval).
+    pub fn with_fire_at(mut self, time: chrono::NaiveTime, tz: Option<String>) -> Self {
+        self.fire_at = Some(time);
+        self.timezone = tz;
+        self
+    }
+
+    /// Resolve timezone string to chrono_tz::Tz (defaults to UTC).
+    fn resolved_tz(&self) -> Tz {
+        self.timezone
+            .as_deref()
+            .and_then(crate::timezone::parse_timezone)
+            .unwrap_or(chrono_tz::UTC)
+    }
 }

 /// Result of a heartbeat check.
@@ -124,6 +144,33 @@ pub enum HeartbeatResult {
    Failed(String),
 }

+/// Compute how long to sleep until the next occurrence of `fire_at` in `tz`.
+///
+/// If the target time today is still in the future, sleep until then.
+/// Otherwise sleep until the same time tomorrow.
+fn duration_until_next_fire(fire_at: chrono::NaiveTime, tz: Tz) -> Duration {
+    let now = chrono::Utc::now().with_timezone(&tz);
+    let today = now.date_naive();
+
+    // Try to build today's target datetime in the given timezone.
+    // `.earliest()` picks the first occurrence if DST creates ambiguity.
+    let candidate = tz.from_local_datetime(&today.and_time(fire_at)).earliest();
+
+    let target = match candidate {
+        Some(t) if t > now => t,
+        _ => {
+            // Already past (or ambiguous) — schedule for tomorrow
+            let tomorrow = today + chrono::Duration::days(1);
+            tz.from_local_datetime(&tomorrow.and_time(fire_at))
+                .earliest()
+                .unwrap_or_else(|| now + chrono::Duration::days(1))
+        }
+    };
+
+    let secs = (target - now).num_seconds().max(1) as u64;
+    Duration::from_secs(secs)
+}
+
 /// Heartbeat runner for proactive periodic execution.
 pub struct HeartbeatRunner {
    config: HeartbeatConfig,
@@ -175,17 +222,39 @@ impl HeartbeatRunner {
            return;
        }

-        tracing::info!(
-            "Starting heartbeat loop with interval {:?}",
-            self.config.interval
-        );
+        // Two scheduling modes:
+        //   fire_at → sleep until the next occurrence (recalculated each iteration)
+        //   interval → tokio::time::interval (drift-free, accounts for loop body time)
+        let mut tick_interval = if self.config.fire_at.is_none() {
+            let mut iv = tokio::time::interval(self.config.interval);
+            // Don't fire immediately on startup.
+            iv.tick().await;
+            Some(iv)
+        } else {
+            None
+        };

-        let mut interval = tokio::time::interval(self.config.interval);
-        // Don't run immediately on startup
-        interval.tick().await;
+        if let Some(fire_at) = self.config.fire_at {
+            tracing::info!(
+                "Starting heartbeat loop: fire daily at {:?} {:?}",
+                fire_at,
+                self.config.timezone
+            );
+        } else {
+            tracing::info!(
+                "Starting heartbeat loop with interval {:?}",
+                self.config.interval
+            );
+        }

        loop {
-            interval.tick().await;
+            if let Some(fire_at) = self.config.fire_at {
+                let sleep_dur = duration_until_next_fire(fire_at, self.config.resolved_tz());
+                tracing::info!("Next heartbeat in {:.1}h", sleep_dur.as_secs_f64() / 3600.0);
+                tokio::time::sleep(sleep_dur).await;
+            } else if let Some(ref mut iv) = tick_interval {
+                iv.tick().await;
+            }

            // Skip during quiet hours
            if self.config.is_quiet_hours() {
@@ -333,7 +402,11 @@ impl HeartbeatRunner {
            return;
        };

-        let user_id = self.config.notify_user_id.as_deref().unwrap_or("default");
+        let user_id = self
+            .config
+            .notify_user_id
+            .as_deref()
+            .unwrap_or_else(|| self.workspace.user_id());

        // Persist to heartbeat conversation and get thread_id
        let thread_id = if let Some(ref store) = self.store {
@@ -362,6 +435,7 @@ impl HeartbeatRunner {
            attachments: Vec::new(),
            metadata: serde_json::json!({
                "source": "heartbeat",
+                "owner_id": self.workspace.user_id(),
            }),
        };

@@ -656,4 +730,63 @@ mod tests {
        ) -> tokio::task::JoinHandle<()> = spawn_heartbeat;
        let _ = _fn_ptr;
    }
+
+    // ==================== fire_at scheduling ====================
+
+    #[test]
+    fn test_default_config_has_no_fire_at() {
+        let config = HeartbeatConfig::default();
+        assert!(config.fire_at.is_none());
+        // Interval-based scheduling should be the default
+        assert_eq!(config.interval, Duration::from_secs(30 * 60));
+    }
+
+    #[test]
+    fn test_with_fire_at_builder() {
+        let time = chrono::NaiveTime::from_hms_opt(9, 0, 0).unwrap();
+        let config =
+            HeartbeatConfig::default().with_fire_at(time, Some("Pacific/Auckland".to_string()));
+        assert_eq!(config.fire_at, Some(time));
+        assert_eq!(config.timezone, Some("Pacific/Auckland".to_string()));
+    }
+
+    #[test]
+    fn test_duration_until_next_fire_is_bounded() {
+        // Result must always be between 1 second and ~24 hours
+        let time = chrono::NaiveTime::from_hms_opt(14, 0, 0).unwrap();
+        let dur = duration_until_next_fire(time, chrono_tz::UTC);
+        assert!(dur.as_secs() >= 1, "duration must be at least 1 second");
+        assert!(
+            dur.as_secs() <= 86_401,
+            "duration must be at most ~24 hours, got {}s",
+            dur.as_secs()
+        );
+    }
+
+    #[test]
+    fn test_duration_until_next_fire_dst_timezone_no_panic() {
+        // Use a timezone with DST (US Eastern) — should never panic
+        let tz: Tz = "America/New_York".parse().unwrap();
+        // Test a range of times including midnight boundaries
+        for hour in [0, 2, 3, 12, 23] {
+            let time = chrono::NaiveTime::from_hms_opt(hour, 30, 0).unwrap();
+            let dur = duration_until_next_fire(time, tz);
+            assert!(dur.as_secs() >= 1);
+            assert!(dur.as_secs() <= 86_401);
+        }
+    }
+
+    #[test]
+    fn test_resolved_tz_defaults_to_utc() {
+        let config = HeartbeatConfig::default();
+        assert_eq!(config.resolved_tz(), chrono_tz::UTC);
+    }
+
+    #[test]
+    fn test_resolved_tz_parses_iana() {
+        let time = chrono::NaiveTime::from_hms_opt(9, 0, 0).unwrap();
+        let config =
+            HeartbeatConfig::default().with_fire_at(time, Some("Europe/London".to_string()));
+        assert_eq!(config.resolved_tz(), chrono_tz::Europe::London);
+    }
 }
@@ -19,7 +19,7 @@ use tokio::task::JoinHandle;
 use uuid::Uuid;

 use crate::channels::IncomingMessage;
-use crate::events::DomainEvent as SseEvent;
+use crate::channels::web::types::SseEvent;

 /// Route context for forwarding job monitor events back to the user's channel.
 #[derive(Debug, Clone)]
@@ -211,6 +211,7 @@ mod tests {
                    job_id: job_id.to_string(),
                    status: "completed".to_string(),
                    session_id: None,
+                    fallback_deliverable: None,
                },
            ))
            .unwrap();
@@ -10,6 +10,7 @@
 //! Lightweight routines execute inline (single LLM call, no scheduler slot).
 //! Full-job routines are delegated to the existing `Scheduler`.

+use std::collections::HashMap;
 use std::sync::Arc;
 use std::sync::atomic::{AtomicUsize, Ordering};
 use std::time::Duration;
@@ -23,19 +24,19 @@ use crate::agent::Scheduler;
 use crate::agent::routine::{
    NotifyConfig, Routine, RoutineAction, RoutineRun, RunStatus, Trigger, next_cron_fire,
 };
-use crate::channels::{IncomingMessage, OutgoingResponse};
+use crate::channels::OutgoingResponse;
 use crate::config::RoutineConfig;
-use crate::context::JobContext;
+use crate::context::{JobContext, JobState};
 use crate::db::Database;
 use crate::error::RoutineError;
 use crate::llm::{
    ChatMessage, CompletionRequest, FinishReason, LlmProvider, ToolCall, ToolCompletionRequest,
 };
-use crate::safety::SafetyLayer;
 use crate::tools::{
    ApprovalContext, ApprovalRequirement, ToolError, ToolRegistry, prepare_tool_params,
 };
 use crate::workspace::Workspace;
+use ironclaw_safety::SafetyLayer;

 enum EventMatcher {
    Message { routine: Routine, regex: Regex },
@@ -60,6 +61,10 @@ pub struct RoutineEngine {
    tools: Arc<ToolRegistry>,
    /// Safety layer for tool output sanitization.
    safety: Arc<SafetyLayer>,
+    /// Timestamp when this engine instance was created. Used by
+    /// `sync_dispatched_runs` to distinguish orphaned runs (from a previous
+    /// process) from actively-watched runs (from this process).
+    boot_time: chrono::DateTime<Utc>,
 }

 impl RoutineEngine {
@@ -85,9 +90,16 @@ impl RoutineEngine {
            scheduler,
            tools,
            safety,
+            boot_time: Utc::now(),
        }
    }

+    /// Expose the running count for integration tests.
+    #[doc(hidden)]
+    pub fn running_count_for_test(&self) -> &Arc<AtomicUsize> {
+        &self.running_count
+    }
+
    /// Refresh the in-memory event trigger cache from DB.
    pub async fn refresh_event_cache(&self) {
        match self.store.list_event_routines().await {
@@ -135,10 +147,19 @@ impl RoutineEngine {

    /// Check incoming message against event triggers. Returns number of routines fired.
    ///
-    /// Called synchronously from the main loop after handle_message(). The actual
-    /// execution is spawned async so this returns quickly.
-    pub async fn check_event_triggers(&self, message: &IncomingMessage) -> usize {
+    /// Accepts only the three fields needed for matching (user scope, channel,
+    /// message content) so callers never need to clone a full `IncomingMessage`.
+    pub async fn check_event_triggers(&self, user_id: &str, channel: &str, content: &str) -> usize {
        let cache = self.event_cache.read().await;
+
+        // Early return if there are no message matchers at all.
+        if !cache
+            .iter()
+            .any(|m| matches!(m, EventMatcher::Message { .. }))
+        {
+            return 0;
+        }
+
        let mut fired = 0;

        // Collect routine IDs for batch query
@@ -155,16 +176,9 @@ impl RoutineEngine {
        }

        // Single batch query instead of N queries
-        let concurrent_counts = match self
-            .store
-            .count_running_routine_runs_batch(&routine_ids)
-            .await
-        {
-            Ok(counts) => counts,
-            Err(e) => {
-                tracing::error!("Failed to batch-load concurrent counts: {}", e);
-                return 0;
-            }
+        let concurrent_counts = match self.batch_concurrent_counts(&routine_ids).await {
+            Some(counts) => counts,
+            None => return 0,
        };

        for matcher in cache.iter() {
@@ -172,17 +186,22 @@ impl RoutineEngine {
                EventMatcher::Message { routine, regex } => (routine, regex),
                EventMatcher::System { .. } => continue,
            };
+
+            if routine.user_id != user_id {
+                continue;
+            }
+
            // Channel filter
            if let Trigger::Event {
                channel: Some(ch), ..
            } = &routine.trigger
-                && ch != &message.channel
+                && ch != channel
            {
                continue;
            }

            // Regex match
-            if !re.is_match(&message.content) {
+            if !re.is_match(content) {
                continue;
            }

@@ -205,7 +224,7 @@ impl RoutineEngine {
                continue;
            }

-            let detail = truncate(&message.content, 200);
+            let detail = truncate(content, 200);
            self.spawn_fire(routine.clone(), "event", Some(detail));
            fired += 1;
        }
@@ -224,6 +243,15 @@ impl RoutineEngine {
        user_id: Option<&str>,
    ) -> usize {
        let cache = self.event_cache.read().await;
+
+        // Early return if there are no system-event matchers at all.
+        if !cache
+            .iter()
+            .any(|m| matches!(m, EventMatcher::System { .. }))
+        {
+            return 0;
+        }
+
        let mut fired = 0;

        // Collect routine IDs for batch query
@@ -240,19 +268,9 @@ impl RoutineEngine {
        }

        // Single batch query instead of N queries
-        let concurrent_counts = match self
-            .store
-            .count_running_routine_runs_batch(&routine_ids)
-            .await
-        {
-            Ok(counts) => counts,
-            Err(e) => {
-                tracing::error!(
-                    "Failed to batch-load concurrent counts for system events: {}",
-                    e
-                );
-                return 0;
-            }
+        let concurrent_counts = match self.batch_concurrent_counts(&routine_ids).await {
+            Some(counts) => counts,
+            None => return 0,
        };

        for matcher in cache.iter() {
@@ -326,6 +344,23 @@ impl RoutineEngine {
        fired
    }

+    /// Batch-load concurrent run counts for a set of routine IDs.
+    ///
+    /// Returns `None` on database error (already logged).
+    async fn batch_concurrent_counts(&self, routine_ids: &[Uuid]) -> Option<HashMap<Uuid, i64>> {
+        match self
+            .store
+            .count_running_routine_runs_batch(routine_ids)
+            .await
+        {
+            Ok(counts) => Some(counts),
+            Err(e) => {
+                tracing::error!("Failed to batch-load concurrent counts: {}", e);
+                None
+            }
+        }
+    }
+
    /// Check all due cron routines and fire them. Called by the cron ticker.
    pub async fn check_cron_triggers(&self) {
        let routines = match self.store.list_due_cron_routines().await {
@@ -360,6 +395,230 @@ impl RoutineEngine {
        }
    }

+    /// Reconcile orphaned full_job routine runs with their linked job outcomes.
+    ///
+    /// Called on each cron tick. Finds routine runs that are still `running`
+    /// with a linked `job_id`, checks the job state, and finalizes the run
+    /// when the job reaches a completed or terminal state.
+    ///
+    /// Only processes runs started **before** this engine's boot time, so it
+    /// never races with `FullJobWatcher` instances from the current process.
+    /// This makes it safe to call on every tick as a crash-recovery mechanism.
+    pub async fn sync_dispatched_runs(&self) {
+        let runs = match self.store.list_dispatched_routine_runs().await {
+            Ok(r) => r,
+            Err(e) => {
+                tracing::error!("Failed to list dispatched routine runs: {}", e);
+                return;
+            }
+        };
+
+        // Only process runs from a previous process instance. Runs started
+        // after boot_time are actively watched by a FullJobWatcher in this
+        // process and should not be finalized here.
+        let orphaned: Vec<_> = runs
+            .into_iter()
+            .filter(|r| r.started_at < self.boot_time)
+            .collect();
+
+        if orphaned.is_empty() {
+            return;
+        }
+
+        tracing::info!(
+            "Recovering {} orphaned dispatched routine runs",
+            orphaned.len()
+        );
+
+        for run in orphaned {
+            let job_id = match run.job_id {
+                Some(id) => id,
+                None => continue, // Should not happen (query filters), but guard anyway
+            };
+
+            // Fetch the linked job
+            let job = match self.store.get_job(job_id).await {
+                Ok(Some(j)) => j,
+                Ok(None) => {
+                    // Orphaned: job record was deleted or never persisted
+                    tracing::warn!(
+                        run_id = %run.id,
+                        job_id = %job_id,
+                        "Linked job not found, marking routine run as failed"
+                    );
+                    self.complete_dispatched_run(
+                        &run,
+                        RunStatus::Failed,
+                        &format!("Linked job {job_id} not found (orphaned)"),
+                    )
+                    .await;
+                    continue;
+                }
+                Err(e) => {
+                    tracing::error!(
+                        run_id = %run.id,
+                        job_id = %job_id,
+                        "Failed to fetch linked job: {}", e
+                    );
+                    continue;
+                }
+            };
+
+            // Map job state to final run status
+            let final_status = match job.state {
+                JobState::Completed | JobState::Submitted | JobState::Accepted => {
+                    Some(RunStatus::Ok)
+                }
+                JobState::Failed | JobState::Cancelled => Some(RunStatus::Failed),
+                // Pending, InProgress, Stuck — still running
+                _ => None,
+            };
+
+            let status = match final_status {
+                Some(s) => s,
+                None => continue, // Job still active, check again next tick
+            };
+
+            // Build summary
+            let summary = if status == RunStatus::Failed {
+                match self.store.get_agent_job_failure_reason(job_id).await {
+                    Ok(Some(reason)) => format!("Job {job_id} failed: {reason}"),
+                    _ => format!("Job {job_id} {}", job.state),
+                }
+            } else {
+                format!("Job {job_id} completed successfully")
+            };
+
+            self.complete_dispatched_run(&run, status, &summary).await;
+        }
+    }
+
+    /// Finalize a dispatched routine run: update DB, update routine runtime,
+    /// persist to conversation thread, and send notification.
+    async fn complete_dispatched_run(&self, run: &RoutineRun, status: RunStatus, summary: &str) {
+        // Complete the run record in DB
+        if let Err(e) = self
+            .store
+            .complete_routine_run(run.id, status, Some(summary), None)
+            .await
+        {
+            tracing::error!(
+                run_id = %run.id,
+                "Failed to complete dispatched routine run: {}", e
+            );
+            return;
+        }
+
+        tracing::info!(
+            run_id = %run.id,
+            status = %status,
+            "Finalized dispatched routine run"
+        );
+
+        // Load the routine to update consecutive_failures and send notification
+        let routine = match self.store.get_routine(run.routine_id).await {
+            Ok(Some(r)) => r,
+            Ok(None) => {
+                tracing::warn!(
+                    run_id = %run.id,
+                    routine_id = %run.routine_id,
+                    "Routine not found for dispatched run finalization"
+                );
+                return;
+            }
+            Err(e) => {
+                tracing::error!(
+                    run_id = %run.id,
+                    "Failed to load routine for dispatched run: {}", e
+                );
+                return;
+            }
+        };
+
+        // Update runtime fields. In crash recovery, execute_routine() never
+        // reached its normal runtime update, so we must advance all fields here.
+        let new_failures = if status == RunStatus::Failed {
+            routine.consecutive_failures + 1
+        } else {
+            0
+        };
+
+        let now = Utc::now();
+        let next_fire = if let Trigger::Cron {
+            ref schedule,
+            ref timezone,
+        } = routine.trigger
+        {
+            next_cron_fire(schedule, timezone.as_deref()).unwrap_or(None)
+        } else {
+            None
+        };
+
+        if let Err(e) = self
+            .store
+            .update_routine_runtime(
+                routine.id,
+                now,
+                next_fire,
+                routine.run_count + 1,
+                new_failures,
+                &routine.state,
+            )
+            .await
+        {
+            tracing::error!(
+                routine = %routine.name,
+                "Failed to update routine runtime after dispatched run: {}", e
+            );
+        }
+
+        // Persist result to the routine's conversation thread
+        let thread_id = match self
+            .store
+            .get_or_create_routine_conversation(routine.id, &routine.name, &routine.user_id)
+            .await
+        {
+            Ok(conv_id) => {
+                let msg = format!("[dispatched] {}: {}", status, summary);
+                if let Err(e) = self
+                    .store
+                    .add_conversation_message(conv_id, "assistant", &msg)
+                    .await
+                {
+                    tracing::error!(
+                        routine = %routine.name,
+                        "Failed to persist dispatched run message: {}", e
+                    );
+                }
+                Some(conv_id.to_string())
+            }
+            Err(e) => {
+                tracing::error!(
+                    routine = %routine.name,
+                    "Failed to get routine conversation: {}", e
+                );
+                None
+            }
+        };
+
+        // Send notification
+        send_notification(
+            &self.notify_tx,
+            &routine.notify,
+            &routine.user_id,
+            &routine.name,
+            status,
+            Some(summary),
+            thread_id.as_deref(),
+        )
+        .await;
+
+        // Note: we do NOT decrement running_count here. In normal flow,
+        // execute_routine() handles that after FullJobWatcher returns.
+        // This sync path only runs for crash recovery (process restarted),
+        // where running_count was already reset to 0.
+    }
+
    /// Fire a routine manually (from tool call or CLI).
    ///
    /// Bypasses cooldown checks (those only apply to cron/event triggers).
@@ -503,6 +762,92 @@ impl RoutineEngine {
    }
 }

+/// Watches a dispatched full_job until the linked scheduler job completes.
+///
+/// Polls `store.get_job(job_id)` at a fixed interval until the job leaves
+/// an active state (Pending/InProgress/Stuck). Maps the final `JobState` to
+/// a `RunStatus` for the routine run.
+struct FullJobWatcher {
+    store: Arc<dyn Database>,
+    job_id: Uuid,
+    routine_name: String,
+}
+
+impl FullJobWatcher {
+    /// Poll interval between DB checks.
+    const POLL_INTERVAL: Duration = Duration::from_secs(5);
+    /// Safety ceiling: 24 hours, derived from POLL_INTERVAL.
+    const MAX_POLLS: u32 = (24 * 60 * 60) / Self::POLL_INTERVAL.as_secs() as u32;
+
+    fn new(store: Arc<dyn Database>, job_id: Uuid, routine_name: String) -> Self {
+        Self {
+            store,
+            job_id,
+            routine_name,
+        }
+    }
+
+    /// Block until the linked job finishes and return the mapped status + summary.
+    async fn wait_for_completion(&self) -> (RunStatus, Option<String>) {
+        let mut polls = 0u32;
+
+        let final_status = loop {
+            // Check job state before sleeping so we finalize promptly
+            // if the job is already done (e.g. fast-failing jobs).
+            match self.store.get_job(self.job_id).await {
+                Ok(Some(job_ctx)) => {
+                    // Use is_parallel_blocking (Pending/InProgress/Stuck) instead
+                    // of is_active (!is_terminal) because routine jobs typically
+                    // stop at Completed — which is NOT terminal but IS finished
+                    // from an execution standpoint.
+                    if !job_ctx.state.is_parallel_blocking() {
+                        break Self::map_job_state(&job_ctx.state);
+                    }
+                }
+                Ok(None) => {
+                    tracing::warn!(
+                        routine = %self.routine_name,
+                        job_id = %self.job_id,
+                        "full_job disappeared from DB while polling"
+                    );
+                    break RunStatus::Failed;
+                }
+                Err(e) => {
+                    tracing::error!(
+                        routine = %self.routine_name,
+                        job_id = %self.job_id,
+                        "Error polling full_job state: {}", e
+                    );
+                    break RunStatus::Failed;
+                }
+            }
+
+            polls += 1;
+            if polls >= Self::MAX_POLLS {
+                tracing::error!(
+                    routine = %self.routine_name,
+                    job_id = %self.job_id,
+                    "full_job timed out after 24 hours, treating as failed"
+                );
+                break RunStatus::Failed;
+            }
+
+            tokio::time::sleep(Self::POLL_INTERVAL).await;
+        };
+
+        let summary = format!("Job {} finished ({})", self.job_id, final_status);
+        (final_status, Some(summary))
+    }
+
+    fn map_job_state(state: &crate::context::JobState) -> RunStatus {
+        use crate::context::JobState;
+        match state {
+            JobState::Failed | JobState::Cancelled => RunStatus::Failed,
+            _ => RunStatus::Ok, // Completed / Submitted / Accepted
+        }
+    }
+}
+
 /// Shared context passed to the execution function.
 struct EngineContext {
    config: RoutineConfig,
@@ -650,6 +995,7 @@ async fn execute_routine(ctx: EngineContext, routine: Routine, run: RoutineRun)
    send_notification(
        &ctx.notify_tx,
        &routine.notify,
+        &routine.user_id,
        &routine.name,
        status,
        summary.as_deref(),
@@ -676,8 +1022,10 @@ fn sanitize_routine_name(name: &str) -> String {
 ///
 /// Fire-and-forget: creates a job via `Scheduler::dispatch_job` (which handles
 /// creation, metadata, persistence, and scheduling), links the routine run to
-/// the job, and returns immediately. The job runs independently via the
-/// existing Worker/Scheduler with full tool access.
+/// the job, then watches it via `FullJobWatcher` until it reaches a
+/// non-active state (not Pending/InProgress/Stuck). Returns the final
+/// `RunStatus` mapped from the job outcome. This keeps the routine run
+/// active for the full job lifetime so concurrency guardrails apply.
 async fn execute_full_job(
    ctx: &EngineContext,
    routine: &Routine,
@@ -694,7 +1042,8 @@ async fn execute_full_job(
            reason: "scheduler not available".to_string(),
        })?;

-    let mut metadata = serde_json::json!({ "max_iterations": max_iterations });
+    let mut metadata =
+        serde_json::json!({ "max_iterations": max_iterations, "owner_id": routine.user_id });
    // Carry the routine's notify config in job metadata so the message tool
    // can resolve channel/target per-job without global state mutation.
    if let Some(channel) = &routine.notify.channel {
@@ -719,25 +1068,30 @@ async fn execute_full_job(
            reason: format!("failed to dispatch job: {e}"),
        })?;

-    // Link the routine run to the dispatched job
-    if let Err(e) = ctx.store.link_routine_run_to_job(run.id, job_id).await {
-        tracing::error!(
-            routine = %routine.name,
-            "Failed to link run to job: {}", e
-        );
-    }
+    // Link the routine run to the dispatched job.
+    // This MUST succeed — if it fails, sync_dispatched_runs() will never find
+    // this run (it filters on job_id IS NOT NULL), leaving it stuck as 'running'
+    // with running_count permanently elevated.
+    ctx.store
+        .link_routine_run_to_job(run.id, job_id)
+        .await
+        .map_err(|e| RoutineError::Database {
+            reason: format!("failed to link run to job: {e}"),
+        })?;

    tracing::info!(
        routine = %routine.name,
        job_id = %job_id,
        max_iterations = max_iterations,
-        "Dispatched full job for routine"
+        "Dispatched full job for routine, watching for completion"
    );

-    let summary = format!(
-        "Dispatched job {job_id} for full execution with tool access (max_iterations: {max_iterations})"
-    );
-    Ok((RunStatus::Ok, Some(summary), None))
+    // Watch the job until it finishes — keeps the routine run active
+    // so concurrency guardrails (running_count, routine_runs status)
+    // remain enforced for the full job lifetime.
+    let watcher = FullJobWatcher::new(ctx.store.clone(), job_id, routine.name.clone());
+    let (status, summary) = watcher.wait_for_completion().await;
+    Ok((status, summary, None))
 }

 /// Execute a lightweight routine with optional tool support.
@@ -777,23 +1131,12 @@ async fn execute_lightweight(
        Err(_) => None,
    };

-    // Build the user-facing prompt
-    let mut full_prompt = String::new();
-    full_prompt.push_str(prompt);
-
-    if !context_parts.is_empty() {
-        full_prompt.push_str("\n\n---\n\n# Context\n\n");
-        full_prompt.push_str(&context_parts.join("\n\n"));
-    }
-
-    if let Some(state) = &state_content {
-        full_prompt.push_str("\n\n---\n\n# Previous State\n\n");
-        full_prompt.push_str(state);
-    }
-
-    full_prompt.push_str(
-        "\n\n---\n\nIf nothing needs attention, reply EXACTLY with: ROUTINE_OK\n\
-         If something needs attention, provide a concise summary.",
+    let full_prompt = build_lightweight_prompt(
+        prompt,
+        &context_parts,
+        state_content.as_deref(),
+        &routine.notify,
+        use_tools,
    );

    // Get system prompt
@@ -837,6 +1180,65 @@ async fn execute_lightweight(
    }
 }

+fn build_lightweight_prompt(
+    prompt: &str,
+    context_parts: &[String],
+    state_content: Option<&str>,
+    notify: &NotifyConfig,
+    use_tools: bool,
+) -> String {
+    let mut full_prompt = String::new();
+    full_prompt.push_str(prompt);
+
+    if notify.on_attention {
+        full_prompt.push_str("\n\n---\n\n# Delivery\n\n");
+        full_prompt.push_str(
+            "If you reply with anything other than ROUTINE_OK, the host will deliver your \
+             reply as the routine notification. Return the message exactly as it should be sent.\n",
+        );
+
+        if let Some(channel) = notify.channel.as_deref() {
+            full_prompt.push_str(&format!(
+                "The configured delivery channel for this routine is `{channel}`.\n"
+            ));
+        }
+
+        if let Some(user) = notify.user.as_deref() {
+            full_prompt.push_str(&format!(
+                "The configured delivery target for this routine is `{user}`.\n"
+            ));
+        }
+
+        full_prompt.push_str(
+            "Do not claim you lack messaging integrations or ask the user to set one up when \
+             a plain reply is sufficient.\n",
+        );
+    }
+
+    if !use_tools {
+        full_prompt.push_str(
+            "\nTools are disabled for this routine run. Do not ask to call tools or describe tool limitations unless they prevent a necessary external action.\n",
+        );
+    }
+
+    if !context_parts.is_empty() {
+        full_prompt.push_str("\n\n---\n\n# Context\n\n");
+        full_prompt.push_str(&context_parts.join("\n\n"));
+    }
+
+    if let Some(state) = state_content {
+        full_prompt.push_str("\n\n---\n\n# Previous State\n\n");
+        full_prompt.push_str(state);
+    }
+
+    full_prompt.push_str(
+        "\n\n---\n\nIf nothing needs attention, reply EXACTLY with: ROUTINE_OK\n\
+         If something needs attention, provide a concise summary.",
+    );
+
+    full_prompt
+}
+
 /// Execute a lightweight routine without tool support (original single-call behavior).
 async fn execute_lightweight_no_tools(
    ctx: &EngineContext,
@@ -894,8 +1296,8 @@ fn handle_text_response(
        };
    }

-    // Check for the "nothing to do" sentinel
-    if content == "ROUTINE_OK" || content.contains("ROUTINE_OK") {
+    // Check for the "nothing to do" sentinel (exact match on trimmed content).
+    if content == "ROUTINE_OK" {
        let total_tokens = Some((total_input_tokens + total_output_tokens) as i32);
        return Ok((RunStatus::Ok, None, total_tokens));
    }
@@ -1207,6 +1609,7 @@ async fn execute_routine_tool(
 async fn send_notification(
    tx: &mpsc::Sender<OutgoingResponse>,
    notify: &NotifyConfig,
+    owner_id: &str,
    routine_name: &str,
    status: RunStatus,
    summary: Option<&str>,
@@ -1243,6 +1646,7 @@ async fn send_notification(
            "source": "routine",
            "routine_name": routine_name,
            "status": status.to_string(),
+            "owner_id": owner_id,
            "notify_user": notify.user,
            "notify_channel": notify.channel,
        }),
@@ -1259,14 +1663,22 @@ pub fn spawn_cron_ticker(
    interval: Duration,
 ) -> tokio::task::JoinHandle<()> {
    tokio::spawn(async move {
-        // Run one check immediately so routines due at startup don't wait
-        // an extra full polling interval.
+        // Recover orphaned runs from a previous process crash before
+        // dispatching any new work, so we don't confuse fresh dispatches
+        // with crash orphans.
+        engine.sync_dispatched_runs().await;
+
+        // Run one cron check immediately so routines due at startup don't
+        // wait an extra full polling interval.
        engine.check_cron_triggers().await;

        let mut ticker = tokio::time::interval(interval);

        loop {
            ticker.tick().await;
+            // Sync first: only processes runs from before boot_time, so it
+            // never races with FullJobWatcher instances from this process.
+            engine.sync_dispatched_runs().await;
            engine.check_cron_triggers().await;
        }
    })
@@ -1376,22 +1788,78 @@ mod tests {
        }
    }

+    #[test]
+    fn test_build_lightweight_prompt_explains_delivery_and_disabled_tools() {
+        let notify = NotifyConfig {
+            channel: Some("telegram".to_string()),
+            user: Some("default".to_string()),
+            on_attention: true,
+            on_failure: true,
+            on_success: false,
+        };
+
+        let prompt = super::build_lightweight_prompt(
+            "Send a Telegram reminder message to the user.",
+            &[],
+            None,
+            &notify,
+            false,
+        );
+
+        assert!(
+            prompt.contains("the host will deliver your reply as the routine notification"),
+            "delivery guidance should explain host delivery: {prompt}",
+        );
+        assert!(
+            prompt.contains("configured delivery channel for this routine is `telegram`"),
+            "delivery guidance should mention telegram channel: {prompt}",
+        );
+        assert!(
+            prompt.contains("Do not claim you lack messaging integrations"),
+            "delivery guidance should suppress fake setup chatter: {prompt}",
+        );
+        assert!(
+            prompt.contains("Tools are disabled for this routine run"),
+            "prompt should explain that tools are disabled: {prompt}",
+        );
+    }
+
+    #[test]
+    fn test_build_lightweight_prompt_skips_delivery_block_when_attention_notifications_disabled() {
+        let notify = NotifyConfig {
+            on_attention: false,
+            ..NotifyConfig::default()
+        };
+
+        let prompt = super::build_lightweight_prompt("Check inbox.", &[], None, &notify, true);
+
+        assert!(
+            !prompt.contains("# Delivery"),
+            "prompt should not include delivery guidance when attention notifications are off: {prompt}",
+        );
+        assert!(
+            !prompt.contains("Tools are disabled for this routine run"),
+            "prompt should not claim tools are disabled when they are enabled: {prompt}",
+        );
+    }
+
    #[test]
    fn test_routine_sentinel_detection_exact_match() {
-        // The execute_lightweight_no_tools checks: content == "ROUTINE_OK" || content.contains("ROUTINE_OK")
-        // After trim(), whitespace is removed
+        // Sentinel detection uses exact match on trimmed content to avoid
+        // false positives from substrings like "NOT_ROUTINE_OK".
        let test_cases = vec![
            ("ROUTINE_OK", true),
            ("  ROUTINE_OK  ", true), // After trim, whitespace is removed so matches
-            ("something ROUTINE_OK something", true),
-            ("ROUTINE_OK is done", true),
-            ("done ROUTINE_OK", true),
+            ("something ROUTINE_OK something", false), // substring no longer matches
+            ("ROUTINE_OK is done", false), // substring no longer matches
+            ("done ROUTINE_OK", false), // substring no longer matches
+            ("NOT_ROUTINE_OK", false), // exact match prevents this
            ("no sentinel here", false),
        ];

        for (content, should_match) in test_cases {
            let trimmed = content.trim();
-            let matches = trimmed == "ROUTINE_OK" || trimmed.contains("ROUTINE_OK");
+            let matches = trimmed == "ROUTINE_OK";
            assert_eq!(
                matches, should_match,
                "Content '{}' sentinel detection should be {}, got {}",
@@ -1505,4 +1973,86 @@ mod tests {
        assert_eq!(snapshot[1].content, "a"); // safety: test-only no-panics CI false positive
        assert_eq!(snapshot[2].content, "b"); // safety: test-only no-panics CI false positive
    }
+
+    /// Regression test for #1317: FullJobWatcher maps terminal job states correctly.
+    #[test]
+    fn test_full_job_watcher_state_mapping() {
+        use crate::context::JobState;
+
+        // Failed/Cancelled → RunStatus::Failed
+        assert_eq!(
+            super::FullJobWatcher::map_job_state(&JobState::Failed),
+            RunStatus::Failed
+        );
+        assert_eq!(
+            super::FullJobWatcher::map_job_state(&JobState::Cancelled),
+            RunStatus::Failed
+        );
+
+        // All other non-active states → RunStatus::Ok
+        assert_eq!(
+            super::FullJobWatcher::map_job_state(&JobState::Completed),
+            RunStatus::Ok
+        );
+        assert_eq!(
+            super::FullJobWatcher::map_job_state(&JobState::Accepted),
+            RunStatus::Ok
+        );
+    }
+
+    /// Verify that job state to run status mapping covers all expected cases.
+    #[test]
+    fn test_job_state_to_run_status_mapping() {
+        use crate::context::JobState;
+
+        // Success states
+        for state in [JobState::Completed, JobState::Submitted, JobState::Accepted] {
+            let status = match state {
+                JobState::Completed | JobState::Submitted | JobState::Accepted => {
+                    Some(RunStatus::Ok)
+                }
+                JobState::Failed | JobState::Cancelled => Some(RunStatus::Failed),
+                _ => None,
+            };
+            assert_eq!(
+                status,
+                Some(RunStatus::Ok),
+                "{:?} should map to RunStatus::Ok",
+                state
+            );
+        }
+
+        // Failure states
+        for state in [JobState::Failed, JobState::Cancelled] {
+            let status = match state {
+                JobState::Completed | JobState::Submitted | JobState::Accepted => {
+                    Some(RunStatus::Ok)
+                }
+                JobState::Failed | JobState::Cancelled => Some(RunStatus::Failed),
+                _ => None,
+            };
+            assert_eq!(
+                status,
+                Some(RunStatus::Failed),
+                "{:?} should map to RunStatus::Failed",
+                state
+            );
+        }
+
+        // Active states (should not finalize)
+        for state in [JobState::Pending, JobState::InProgress, JobState::Stuck] {
+            let status = match state {
+                JobState::Completed | JobState::Submitted | JobState::Accepted => {
+                    Some(RunStatus::Ok)
+                }
+                JobState::Failed | JobState::Cancelled => Some(RunStatus::Failed),
+                _ => None,
+            };
+            assert_eq!(
+                status, None,
+                "{:?} should not finalize the routine run",
+                state
+            );
+        }
+    }
 }
@@ -9,11 +9,11 @@ use tokio::task::JoinHandle;
 use uuid::Uuid;

 use crate::agent::task::{Task, TaskContext, TaskOutput};
+use crate::channels::web::types::SseEvent;
 use crate::config::AgentConfig;
 use crate::context::{ContextManager, JobContext, JobState};
 use crate::db::Database;
 use crate::error::{Error, JobError};
-use crate::events::DomainEvent as SseEvent;
 use crate::hooks::HookRegistry;
 use crate::llm::LlmProvider;
 use crate::safety::SafetyLayer;
@@ -272,7 +272,6 @@ impl Scheduler {
                sse_tx: self.sse_tx.clone(),
                approval_context,
                http_interceptor: self.http_interceptor.clone(),
-                event_bus: None,
            };
            let worker = Worker::new(job_id, deps);

@@ -22,11 +22,17 @@ pub struct StuckJob {
    pub repair_attempts: u32,
 }

-/// Backward-compatible alias for `ToolFailureRecord`.
-///
-/// The canonical type now lives in `crate::models::tool_failure` to break
-/// the circular dependency between `db` and `agent`.
-pub type BrokenTool = crate::models::tool_failure::ToolFailureRecord;
+/// A tool that has been detected as broken.
+#[derive(Debug, Clone)]
+pub struct BrokenTool {
+    pub name: String,
+    pub failure_count: u32,
+    pub last_error: Option<String>,
+    pub first_failure: DateTime<Utc>,
+    pub last_failure: DateTime<Utc>,
+    pub last_build_result: Option<serde_json::Value>,
+    pub repair_attempts: u32,
+}

 /// Result of a repair attempt.
 #[derive(Debug)]
@@ -60,14 +66,10 @@ pub trait SelfRepair: Send + Sync {
 /// Default self-repair implementation.
 pub struct DefaultSelfRepair {
    context_manager: Arc<ContextManager>,
-    // TODO: use for time-based stuck detection (currently only max_repair_attempts is checked)
-    #[allow(dead_code)]
    stuck_threshold: Duration,
    max_repair_attempts: u32,
    store: Option<Arc<dyn Database>>,
    builder: Option<Arc<dyn SoftwareBuilder>>,
-    // TODO: use for tool hot-reload after repair
-    #[allow(dead_code)]
    tools: Option<Arc<ToolRegistry>>,
 }

@@ -89,15 +91,13 @@ impl DefaultSelfRepair {
    }

    /// Add a Store for tool failure tracking.
-    #[allow(dead_code)] // TODO: wire up in main.rs when persistence is needed
-    pub(crate) fn with_store(mut self, store: Arc<dyn Database>) -> Self {
+    pub fn with_store(mut self, store: Arc<dyn Database>) -> Self {
        self.store = Some(store);
        self
    }

    /// Add a Builder and ToolRegistry for automatic tool repair.
-    #[allow(dead_code)] // TODO: wire up in main.rs when auto-repair is needed
-    pub(crate) fn with_builder(
+    pub fn with_builder(
        mut self,
        builder: Arc<dyn SoftwareBuilder>,
        tools: Arc<ToolRegistry>,
@@ -118,18 +118,30 @@ impl SelfRepair for DefaultSelfRepair {
            if let Ok(ctx) = self.context_manager.get_context(job_id).await
                && ctx.state == JobState::Stuck
            {
-                let stuck_duration = ctx
-                    .started_at
-                    .map(|start| {
-                        let now = Utc::now();
-                        let duration = now.signed_duration_since(start);
+                // Measure stuck_duration from the most recent Stuck transition,
+                // not from started_at (which reflects when the job first ran).
+                let stuck_since = ctx
+                    .transitions
+                    .iter()
+                    .rev()
+                    .find(|t| t.to == JobState::Stuck)
+                    .map(|t| t.timestamp);
+
+                let stuck_duration = stuck_since
+                    .map(|ts| {
+                        let duration = Utc::now().signed_duration_since(ts);
                        Duration::from_secs(duration.num_seconds().max(0) as u64)
                    })
                    .unwrap_or_default();

+                // Only report jobs that have been stuck long enough
+                if stuck_duration < self.stuck_threshold {
+                    continue;
+                }
+
                stuck_jobs.push(StuckJob {
                    job_id,
-                    last_activity: ctx.started_at.unwrap_or(ctx.created_at),
+                    last_activity: stuck_since.unwrap_or(ctx.created_at),
                    stuck_duration,
                    last_error: None,
                    repair_attempts: ctx.repair_attempts,
@@ -267,9 +279,8 @@ impl SelfRepair for DefaultSelfRepair {
                    tracing::warn!("Failed to mark tool as repaired: {}", e);
                }

-                // Log if the tool was auto-registered
                if result.registered {
-                    tracing::info!("Repaired tool '{}' auto-registered", tool.name);
+                    tracing::info!("Repaired tool '{}' auto-registered by builder", tool.name);
                }

                Ok(RepairResult::Success {
@@ -411,7 +422,8 @@ mod tests {
        .unwrap()
        .unwrap();

-        let repair = DefaultSelfRepair::new(cm, Duration::from_secs(60), 3);
+        // Use zero threshold so the just-stuck job is detected immediately.
+        let repair = DefaultSelfRepair::new(cm, Duration::from_secs(0), 3);
        let stuck = repair.detect_stuck_jobs().await;
        assert_eq!(stuck.len(), 1);
        assert_eq!(stuck[0].job_id, job_id);
@@ -477,6 +489,98 @@ mod tests {
        );
    }

+    #[tokio::test]
+    async fn detect_stuck_jobs_filters_by_threshold() {
+        let cm = Arc::new(ContextManager::new(10));
+        let job_id = cm.create_job("Stuck job", "desc").await.unwrap();
+
+        // Transition to InProgress, then to Stuck.
+        cm.update_context(job_id, |ctx| ctx.transition_to(JobState::InProgress, None))
+            .await
+            .unwrap()
+            .unwrap();
+        cm.update_context(job_id, |ctx| {
+            ctx.transition_to(JobState::Stuck, Some("timed out".to_string()))
+        })
+        .await
+        .unwrap()
+        .unwrap();
+
+        // Use a very large threshold (1 hour). Job just became stuck, so
+        // stuck_duration < threshold. It should be filtered out.
+        let repair = DefaultSelfRepair::new(cm, Duration::from_secs(3600), 3);
+        let stuck = repair.detect_stuck_jobs().await;
+        assert!(
+            stuck.is_empty(),
+            "Job stuck for <1s should be filtered by 1h threshold"
+        );
+    }
+
+    #[tokio::test]
+    async fn detect_stuck_jobs_includes_when_over_threshold() {
+        let cm = Arc::new(ContextManager::new(10));
+        let job_id = cm.create_job("Stuck job", "desc").await.unwrap();
+
+        // Transition to InProgress, then to Stuck.
+        cm.update_context(job_id, |ctx| ctx.transition_to(JobState::InProgress, None))
+            .await
+            .unwrap()
+            .unwrap();
+        cm.update_context(job_id, |ctx| {
+            ctx.transition_to(JobState::Stuck, Some("timed out".to_string()))
+        })
+        .await
+        .unwrap()
+        .unwrap();
+
+        // Use a zero threshold -- any stuck duration should be included.
+        let repair = DefaultSelfRepair::new(cm, Duration::from_secs(0), 3);
+        let stuck = repair.detect_stuck_jobs().await;
+        assert_eq!(stuck.len(), 1, "Job should be detected with zero threshold");
+        assert_eq!(stuck[0].job_id, job_id);
+    }
+
+    /// Regression: stuck_duration must be measured from the Stuck transition,
+    /// not from started_at. A job that ran for 2 hours before becoming stuck
+    /// should NOT immediately exceed a 5-minute threshold.
+    #[tokio::test]
+    async fn stuck_duration_measured_from_stuck_transition_not_started_at() {
+        let cm = Arc::new(ContextManager::new(10));
+        let job_id = cm.create_job("Long runner", "desc").await.unwrap();
+
+        // Transition to InProgress (sets started_at to now).
+        cm.update_context(job_id, |ctx| ctx.transition_to(JobState::InProgress, None))
+            .await
+            .unwrap()
+            .unwrap();
+
+        // Backdate started_at to 2 hours ago to simulate a long-running job.
+        cm.update_context(job_id, |ctx| {
+            ctx.started_at = Some(Utc::now() - chrono::Duration::hours(2));
+            Ok::<(), crate::error::Error>(())
+        })
+        .await
+        .unwrap()
+        .unwrap();
+
+        // Now transition to Stuck (stuck transition timestamp is ~now).
+        cm.update_context(job_id, |ctx| {
+            ctx.transition_to(JobState::Stuck, Some("wedged".into()))
+        })
+        .await
+        .unwrap()
+        .unwrap();
+
+        // With a 5-minute threshold, the job JUST became stuck — should NOT be detected.
+        let repair = DefaultSelfRepair::new(cm, Duration::from_secs(300), 3);
+        let stuck = repair.detect_stuck_jobs().await;
+        assert!(
+            stuck.is_empty(),
+            "Job stuck for <1s should not exceed 5min threshold, \
+             but stuck_duration was computed from started_at (2h ago)"
+        );
+    }
+
    #[tokio::test]
    async fn detect_broken_tools_returns_empty_without_store() {
        let cm = Arc::new(ContextManager::new(10));
@@ -509,4 +613,148 @@ mod tests {
            result
        );
    }
+
+    /// Mock SoftwareBuilder that returns a successful build result.
+    struct MockBuilder {
+        build_count: std::sync::atomic::AtomicU32,
+    }
+
+    impl MockBuilder {
+        fn new() -> Self {
+            Self {
+                build_count: std::sync::atomic::AtomicU32::new(0),
+            }
+        }
+
+        fn builds(&self) -> u32 {
+            self.build_count.load(std::sync::atomic::Ordering::Relaxed)
+        }
+    }
+
+    #[async_trait]
+    impl crate::tools::SoftwareBuilder for MockBuilder {
+        async fn analyze(
+            &self,
+            _description: &str,
+        ) -> Result<crate::tools::BuildRequirement, crate::error::ToolError> {
+            Ok(crate::tools::BuildRequirement {
+                name: "mock-tool".to_string(),
+                description: "mock".to_string(),
+                software_type: crate::tools::SoftwareType::WasmTool,
+                language: crate::tools::Language::Rust,
+                input_spec: None,
+                output_spec: None,
+                dependencies: vec![],
+                capabilities: vec![],
+            })
+        }
+
+        async fn build(
+            &self,
+            requirement: &crate::tools::BuildRequirement,
+        ) -> Result<crate::tools::BuildResult, crate::error::ToolError> {
+            self.build_count
+                .fetch_add(1, std::sync::atomic::Ordering::Relaxed);
+            Ok(crate::tools::BuildResult {
+                build_id: Uuid::new_v4(),
+                requirement: requirement.clone(),
+                artifact_path: std::path::PathBuf::from("/tmp/mock.wasm"),
+                logs: vec![],
+                success: true,
+                error: None,
+                started_at: Utc::now(),
+                completed_at: Utc::now(),
+                iterations: 1,
+                validation_warnings: vec![],
+                tests_passed: 1,
+                tests_failed: 0,
+                registered: true,
+            })
+        }
+
+        async fn repair(
+            &self,
+            _result: &crate::tools::BuildResult,
+            _error: &str,
+        ) -> Result<crate::tools::BuildResult, crate::error::ToolError> {
+            unimplemented!("not needed for this test")
+        }
+    }
+
+    /// E2E test: stuck job detected -> repaired -> transitions back to InProgress,
+    /// and broken tool detected -> builder invoked -> tool marked repaired.
+    #[cfg(feature = "libsql")]
+    #[tokio::test]
+    async fn e2e_stuck_job_repair_and_tool_rebuild() {
+        // --- Setup ---
+        let cm = Arc::new(ContextManager::new(10));
+        let job_id = cm.create_job("E2E stuck job", "desc").await.unwrap();
+
+        // Transition job: Pending -> InProgress -> Stuck
+        cm.update_context(job_id, |ctx| ctx.transition_to(JobState::InProgress, None))
+            .await
+            .unwrap()
+            .unwrap();
+        cm.update_context(job_id, |ctx| {
+            ctx.transition_to(JobState::Stuck, Some("deadlocked".to_string()))
+        })
+        .await
+        .unwrap()
+        .unwrap();
+
+        // Create a mock builder and a real test database (for store)
+        let builder = Arc::new(MockBuilder::new());
+        let tools = Arc::new(ToolRegistry::new());
+        let (db, _tmp_dir) = crate::testing::test_db().await;
+
+        // Create self-repair with zero threshold (detect immediately),
+        // wired with store, builder, and tools.
+        let repair = DefaultSelfRepair::new(Arc::clone(&cm), Duration::from_secs(0), 3)
+            .with_store(Arc::clone(&db))
+            .with_builder(
+                Arc::clone(&builder) as Arc<dyn crate::tools::SoftwareBuilder>,
+                tools,
+            );
+
+        // --- Phase 1: Detect and repair stuck job ---
+        let stuck_jobs = repair.detect_stuck_jobs().await;
+        assert_eq!(stuck_jobs.len(), 1, "Should detect the stuck job");
+        assert_eq!(stuck_jobs[0].job_id, job_id);
+
+        let result = repair.repair_stuck_job(&stuck_jobs[0]).await.unwrap();
+        assert!(
+            matches!(result, RepairResult::Success { .. }),
+            "Job repair should succeed: {:?}",
+            result
+        );
+
+        // Verify job transitioned back to InProgress
+        let ctx = cm.get_context(job_id).await.unwrap();
+        assert_eq!(
+            ctx.state,
+            JobState::InProgress,
+            "Job should be back to InProgress after repair"
+        );
+
+        // --- Phase 2: Repair a broken tool via builder ---
+        let broken = BrokenTool {
+            name: "broken-wasm-tool".to_string(),
+            failure_count: 10,
+            last_error: Some("panic in tool execution".to_string()),
+            first_failure: Utc::now() - chrono::Duration::hours(1),
+            last_failure: Utc::now(),
+            last_build_result: None,
+            repair_attempts: 0,
+        };
+
+        let tool_result = repair.repair_broken_tool(&broken).await.unwrap();
+        assert!(
+            matches!(tool_result, RepairResult::Success { .. }),
+            "Tool repair should succeed with mock builder: {:?}",
+            tool_result
+        );
+
+        // Verify builder was actually invoked
+        assert_eq!(builder.builds(), 1, "Builder should have been called once");
+    }
 }
@@ -16,8 +16,8 @@ use chrono::{DateTime, TimeDelta, Utc};
 use serde::{Deserialize, Serialize};
 use uuid::Uuid;

+use crate::channels::web::util::truncate_preview;
 use crate::llm::{ChatMessage, ToolCall};
-use crate::util::truncate_preview;

 /// A session containing one or more threads.
 #[derive(Debug, Clone, Serialize, Deserialize)]
@@ -133,28 +133,6 @@ pub enum ThreadState {
    Interrupted,
 }

-impl ThreadState {
-    /// Check whether a transition from this state to `target` is valid.
-    pub fn can_transition_to(self, target: ThreadState) -> bool {
-        use ThreadState::*;
-        matches!(
-            (self, target),
-            // From Idle
-            (Idle, Processing) |
-            // From Processing
-            (Processing, Idle) |
-            (Processing, AwaitingApproval) |
-            (Processing, Interrupted) |
-            // From AwaitingApproval
-            (AwaitingApproval, Idle) |
-            (AwaitingApproval, Processing) |
-            (AwaitingApproval, Interrupted) |
-            // From Interrupted
-            (Interrupted, Idle)
-        )
-    }
-}
-
 /// Pending auth token request.
 ///
 /// Auth mode TTL — must stay in sync with
@@ -210,6 +188,15 @@ pub struct PendingApproval {
    /// through the approval flow even if the approval message lacks timezone.
    #[serde(default)]
    pub user_timezone: Option<String>,
+    /// Whether the "always" auto-approve option should be offered to the user.
+    /// `false` when the tool returned `ApprovalRequirement::Always` (e.g.
+    /// destructive shell commands), meaning every invocation must be confirmed.
+    #[serde(default = "default_true")]
+    pub allow_always: bool,
+}
+
+fn default_true() -> bool {
+    true
 }

 /// A conversation thread within a session.
@@ -219,8 +206,8 @@ pub struct Thread {
    pub id: Uuid,
    /// Parent session ID.
    pub session_id: Uuid,
-    /// Current state. Private — use `state()` to read, transition methods to mutate.
-    state: ThreadState,
+    /// Current state.
+    pub state: ThreadState,
    /// Turns in this thread.
    pub turns: Vec<Turn>,
    /// When the thread was created.
@@ -270,33 +257,6 @@ impl Thread {
        }
    }

-    /// Get the current thread state.
-    pub fn state(&self) -> ThreadState {
-        self.state
-    }
-
-    /// Force-reset the state to Idle (for clear/restore operations that
-    /// bypass normal transitions). Prefer the transition methods for
-    /// normal state changes.
-    pub fn reset_to_idle(&mut self) {
-        self.state = ThreadState::Idle;
-        self.updated_at = Utc::now();
-    }
-
-    /// Force-set state to Processing (for approval flow resumption where
-    /// state was AwaitingApproval → Processing). Validates the transition.
-    pub fn set_processing(&mut self) -> Result<(), String> {
-        if !self.state.can_transition_to(ThreadState::Processing) {
-            return Err(format!(
-                "Cannot transition from {:?} to Processing",
-                self.state
-            ));
-        }
-        self.state = ThreadState::Processing;
-        self.updated_at = Utc::now();
-        Ok(())
-    }
-
    /// Get the current turn number (1-indexed for display).
    pub fn turn_number(&self) -> usize {
        self.turns.len() + 1
@@ -567,8 +527,8 @@ pub struct Turn {
    pub response: Option<String>,
    /// Tool calls made during this turn.
    pub tool_calls: Vec<TurnToolCall>,
-    /// Turn state. Private — use `state()` to read, transition methods to mutate.
-    state: TurnState,
+    /// Turn state.
+    pub state: TurnState,
    /// When the turn started.
    pub started_at: DateTime<Utc>,
    /// When the turn completed.
@@ -598,11 +558,6 @@ impl Turn {
        }
    }

-    /// Get the current turn state.
-    pub fn state(&self) -> TurnState {
-        self.state
-    }
-
    /// Complete this turn.
    pub fn complete(&mut self, response: impl Into<String>) {
        self.response = Some(response.into());
@@ -683,11 +638,11 @@ mod tests {
        let mut thread = Thread::new(Uuid::new_v4());

        thread.start_turn("Hello");
-        assert_eq!(thread.state(), ThreadState::Processing);
+        assert_eq!(thread.state, ThreadState::Processing);
        assert_eq!(thread.turns.len(), 1);

        thread.complete_turn("Hi there!");
-        assert_eq!(thread.state(), ThreadState::Idle);
+        assert_eq!(thread.state, ThreadState::Idle);
        assert_eq!(thread.turns[0].response, Some("Hi there!".to_string()));
    }

@@ -737,7 +692,7 @@ mod tests {
        assert_eq!(thread.turns[0].response, Some("Hi there!".to_string()));
        assert_eq!(thread.turns[1].user_input, "How are you?");
        assert_eq!(thread.turns[1].response, Some("I'm good!".to_string()));
-        assert_eq!(thread.state(), ThreadState::Idle);
+        assert_eq!(thread.state, ThreadState::Idle);
    }

    #[test]
@@ -837,7 +792,7 @@ mod tests {

        assert_eq!(thread.id, specific_id);
        assert_eq!(thread.session_id, session_id);
-        assert_eq!(thread.state(), ThreadState::Idle);
+        assert_eq!(thread.state, ThreadState::Idle);
        assert!(thread.turns.is_empty());
    }

@@ -875,7 +830,7 @@ mod tests {

        // Should clear all turns and stay idle
        assert!(thread.turns.is_empty());
-        assert_eq!(thread.state(), ThreadState::Idle);
+        assert_eq!(thread.state, ThreadState::Idle);
    }

    #[test]
@@ -994,17 +949,17 @@ mod tests {
        let mut thread = Thread::new(Uuid::new_v4());

        thread.start_turn("do something");
-        assert_eq!(thread.state(), ThreadState::Processing);
+        assert_eq!(thread.state, ThreadState::Processing);

        thread.interrupt();
-        assert_eq!(thread.state(), ThreadState::Interrupted);
+        assert_eq!(thread.state, ThreadState::Interrupted);

        let last_turn = thread.last_turn().unwrap();
-        assert_eq!(last_turn.state(), TurnState::Interrupted);
+        assert_eq!(last_turn.state, TurnState::Interrupted);
        assert!(last_turn.completed_at.is_some());

        thread.resume();
-        assert_eq!(thread.state(), ThreadState::Idle);
+        assert_eq!(thread.state, ThreadState::Idle);
    }

    #[test]
@@ -1012,15 +967,15 @@ mod tests {
        let mut thread = Thread::new(Uuid::new_v4());

        // Idle thread: resume should be a no-op
-        assert_eq!(thread.state(), ThreadState::Idle);
+        assert_eq!(thread.state, ThreadState::Idle);
        thread.resume();
-        assert_eq!(thread.state(), ThreadState::Idle);
+        assert_eq!(thread.state, ThreadState::Idle);

        // Processing thread: resume should not change state
        thread.start_turn("work");
-        assert_eq!(thread.state(), ThreadState::Processing);
+        assert_eq!(thread.state, ThreadState::Processing);
        thread.resume();
-        assert_eq!(thread.state(), ThreadState::Processing);
+        assert_eq!(thread.state, ThreadState::Processing);
    }

    #[test]
@@ -1030,10 +985,10 @@ mod tests {
        thread.start_turn("risky operation");
        thread.fail_turn("connection timed out");

-        assert_eq!(thread.state(), ThreadState::Idle);
+        assert_eq!(thread.state, ThreadState::Idle);

        let turn = thread.last_turn().unwrap();
-        assert_eq!(turn.state(), TurnState::Failed);
+        assert_eq!(turn.state, TurnState::Failed);
        assert_eq!(turn.error, Some("connection timed out".to_string()));
        assert!(turn.response.is_none());
        assert!(turn.completed_at.is_some());
@@ -1132,7 +1087,7 @@ mod tests {

        // Completing a turn when there are no turns should be a safe no-op
        thread.complete_turn("phantom response");
-        assert_eq!(thread.state(), ThreadState::Idle);
+        assert_eq!(thread.state, ThreadState::Idle);
        assert!(thread.turns.is_empty());
    }

@@ -1142,7 +1097,7 @@ mod tests {

        // Failing a turn when there are no turns should be a safe no-op
        thread.fail_turn("phantom error");
-        assert_eq!(thread.state(), ThreadState::Idle);
+        assert_eq!(thread.state, ThreadState::Idle);
        assert!(thread.turns.is_empty());
    }

@@ -1160,10 +1115,11 @@ mod tests {
            context_messages: vec![ChatMessage::user("do it")],
            deferred_tool_calls: vec![],
            user_timezone: None,
+            allow_always: false,
        };

        thread.await_approval(approval);
-        assert_eq!(thread.state(), ThreadState::AwaitingApproval);
+        assert_eq!(thread.state, ThreadState::AwaitingApproval);
        assert!(thread.pending_approval.is_some());

        let taken = thread.take_pending_approval();
@@ -1186,12 +1142,13 @@ mod tests {
            context_messages: vec![],
            deferred_tool_calls: vec![],
            user_timezone: None,
+            allow_always: true,
        };

        thread.await_approval(approval);
        thread.clear_pending_approval();

-        assert_eq!(thread.state(), ThreadState::Idle);
+        assert_eq!(thread.state, ThreadState::Idle);
        assert!(thread.pending_approval.is_none());
    }

@@ -1210,7 +1167,7 @@ mod tests {
        // Mutably modify through accessor
        session.active_thread_mut().unwrap().start_turn("test");
        assert_eq!(
-            session.active_thread().unwrap().state(),
+            session.active_thread().unwrap().state,
            ThreadState::Processing
        );
    }
@@ -1435,71 +1392,4 @@ mod tests {
        );
        assert!(tool_result_content.ends_with("..."));
    }
-
-    #[test]
-    fn thread_state_transition_table() {
-        use ThreadState::*;
-
-        // Valid transitions
-        assert!(Idle.can_transition_to(Processing));
-        assert!(Processing.can_transition_to(Idle));
-        assert!(Processing.can_transition_to(AwaitingApproval));
-        assert!(Processing.can_transition_to(Interrupted));
-        assert!(AwaitingApproval.can_transition_to(Idle));
-        assert!(AwaitingApproval.can_transition_to(Processing));
-        assert!(AwaitingApproval.can_transition_to(Interrupted));
-        assert!(Interrupted.can_transition_to(Idle));
-
-        // Invalid transitions
-        assert!(!Idle.can_transition_to(Idle));
-        assert!(!Idle.can_transition_to(AwaitingApproval));
-        assert!(!Idle.can_transition_to(Interrupted));
-        assert!(!Idle.can_transition_to(Completed));
-        assert!(!Processing.can_transition_to(Processing));
-        assert!(!Processing.can_transition_to(Completed));
-        assert!(!AwaitingApproval.can_transition_to(AwaitingApproval));
-        assert!(!Interrupted.can_transition_to(Processing));
-        assert!(!Interrupted.can_transition_to(Interrupted));
-        assert!(!Completed.can_transition_to(Idle));
-        assert!(!Completed.can_transition_to(Processing));
-    }
-
-    #[test]
-    fn thread_state_is_private() {
-        let thread = Thread::new(Uuid::new_v4());
-        // Can read via accessor
-        assert_eq!(thread.state(), ThreadState::Idle);
-    }
-
-    #[test]
-    fn set_processing_validates_transition() {
-        let mut thread = Thread::new(Uuid::new_v4());
-
-        // Idle → Processing: valid
-        assert!(thread.set_processing().is_ok());
-        assert_eq!(thread.state(), ThreadState::Processing);
-
-        // Processing → Processing: invalid
-        assert!(thread.set_processing().is_err());
-
-        // Complete the turn so we can test from AwaitingApproval
-        thread.complete_turn("done");
-
-        // AwaitingApproval → Processing: valid
-        thread.start_turn("test");
-        thread.await_approval(PendingApproval {
-            request_id: Uuid::new_v4(),
-            tool_name: "echo".into(),
-            parameters: serde_json::json!({}),
-            display_parameters: serde_json::json!({}),
-            description: "test".into(),
-            tool_call_id: "tc1".into(),
-            context_messages: vec![],
-            deferred_tool_calls: vec![],
-            user_timezone: None,
-        });
-        assert_eq!(thread.state(), ThreadState::AwaitingApproval);
-        assert!(thread.set_processing().is_ok());
-        assert_eq!(thread.state(), ThreadState::Processing);
-    }
 }
@@ -136,26 +136,30 @@ impl SessionManager {
        if let Some(ext_tid) = external_thread_id
            && let Ok(ext_uuid) = Uuid::parse_str(ext_tid)
        {
-            // Atomic check-and-insert: acquire write lock for the entire
-            // sequence to prevent TOCTOU races where another task could map
-            // this UUID between our check and insert.
-            let mut thread_map = self.thread_map.write().await;
+            let thread_map = self.thread_map.read().await;
            let mapped_elsewhere = thread_map.values().any(|&v| v == ext_uuid);
+            drop(thread_map);

            if !mapped_elsewhere {
                let sess = session.lock().await;
-                let exists_in_session = sess.threads.contains_key(&ext_uuid);
-                drop(sess);
+                if sess.threads.contains_key(&ext_uuid) {
+                    drop(sess);

-                if exists_in_session {
-                    thread_map.insert(key, ext_uuid);
-                    drop(thread_map);
-                    // Ensure undo manager exists
-                    let mut undo_managers = self.undo_managers.write().await;
-                    undo_managers
-                        .entry(ext_uuid)
-                        .or_insert_with(|| Arc::new(Mutex::new(UndoManager::new())));
-                    return (session, ext_uuid);
+                    let mut thread_map = self.thread_map.write().await;
+                    // Re-check after acquiring write lock to prevent race condition
+                    // where another task mapped this UUID between our read and write.
+                    if !thread_map.values().any(|&v| v == ext_uuid) {
+                        thread_map.insert(key, ext_uuid);
+                        drop(thread_map);
+                        // Ensure undo manager exists
+                        let mut undo_managers = self.undo_managers.write().await;
+                        undo_managers
+                            .entry(ext_uuid)
+                            .or_insert_with(|| Arc::new(Mutex::new(UndoManager::new())));
+                        return (session, ext_uuid);
+                    }
+                    // If it was mapped elsewhere while we were unlocked, fall through
+                    // to create a new thread, preserving channel isolation.
                }
            }
        }
@@ -382,6 +382,8 @@ pub enum SubmissionResult {
        description: String,
        /// Parameters being passed.
        parameters: serde_json::Value,
+        /// Whether "always" auto-approve should be offered to the user.
+        allow_always: bool,
    },

    /// Successfully processed (for control commands).
@@ -427,6 +429,14 @@ impl SubmissionResult {
            message: message.into(),
        }
    }
+
+    /// Create a non-error status message (e.g., for blocking states like approval waiting).
+    /// Uses Ok variant to avoid "Error:" prefix in rendering.
+    pub fn pending(message: impl Into<String>) -> Self {
+        Self::Ok {
+            message: Some(message.into()),
+        }
+    }
 }

 #[cfg(test)]
@@ -16,12 +16,12 @@ use crate::agent::dispatcher::{
 };
 use crate::agent::session::{PendingApproval, Session, ThreadState};
 use crate::agent::submission::SubmissionResult;
+use crate::channels::web::util::truncate_preview;
 use crate::channels::{IncomingMessage, StatusUpdate};
 use crate::context::JobContext;
 use crate::error::Error;
 use crate::llm::{ChatMessage, ToolCall};
 use crate::tools::redact_params;
-use crate::util::truncate_preview;

 const FORGED_THREAD_ID_ERROR: &str = "Invalid or unauthorized thread ID.";

@@ -186,9 +186,70 @@ impl Agent {
            "Processing user input"
        );

-        // Safety validation BEFORE state check — these don't need the session
-        // lock and are the slowest part, so run them first. Then we can do the
-        // state check + start_turn atomically under one lock (TOCTOU fix).
+        // First check thread state without holding lock during I/O
+        let (thread_state, approval_context) = {
+            let sess = session.lock().await;
+            let thread = sess
+                .threads
+                .get(&thread_id)
+                .ok_or_else(|| Error::from(crate::error::JobError::NotFound { id: thread_id }))?;
+            let approval_context = thread.pending_approval.as_ref().map(|a| {
+                let desc_preview =
+                    crate::agent::agent_loop::truncate_for_preview(&a.description, 80);
+                (a.tool_name.clone(), desc_preview)
+            });
+            (thread.state, approval_context)
+        };
+
+        tracing::debug!(
+            message_id = %message.id,
+            thread_id = %thread_id,
+            thread_state = ?thread_state,
+            "Checked thread state"
+        );
+
+        // Check thread state
+        match thread_state {
+            ThreadState::Processing => {
+                tracing::warn!(
+                    message_id = %message.id,
+                    thread_id = %thread_id,
+                    "Thread is processing, rejecting new input"
+                );
+                return Ok(SubmissionResult::error(
+                    "Turn in progress. Use /interrupt to cancel.",
+                ));
+            }
+            ThreadState::AwaitingApproval => {
+                tracing::warn!(
+                    message_id = %message.id,
+                    thread_id = %thread_id,
+                    "Thread awaiting approval, rejecting new input"
+                );
+                let msg = match approval_context {
+                    Some((tool_name, desc_preview)) => format!(
+                        "Waiting for approval: {tool_name} — {desc_preview}. Use /interrupt to cancel."
+                    ),
+                    None => "Waiting for approval. Use /interrupt to cancel.".to_string(),
+                };
+                return Ok(SubmissionResult::pending(msg));
+            }
+            ThreadState::Completed => {
+                tracing::warn!(
+                    message_id = %message.id,
+                    thread_id = %thread_id,
+                    "Thread completed, rejecting new input"
+                );
+                return Ok(SubmissionResult::error(
+                    "Thread completed. Use /thread new.",
+                ));
+            }
+            ThreadState::Idle | ThreadState::Interrupted => {
+                // Can proceed
+            }
+        }
+
+        // Safety validation for user input
        let validation = self.safety().validate_input(content);
        if !validation.is_valid {
            let details = validation
@@ -238,10 +299,7 @@ impl Agent {
        // Natural language goes through the agentic loop
        // Job tools (create_job, list_jobs, etc.) are in the tool registry

-        // Check thread state and auto-compact under a single lock acquisition.
-        // The state check must happen under the lock to prevent TOCTOU races
-        // where another task could change the state between our check and
-        // the start_turn call.
+        // Auto-compact if needed BEFORE adding new turn
        {
            let mut sess = session.lock().await;
            let thread = sess
@@ -249,35 +307,6 @@ impl Agent {
                .get_mut(&thread_id)
                .ok_or_else(|| Error::from(crate::error::JobError::NotFound { id: thread_id }))?;

-            let thread_state = thread.state();
-            tracing::debug!(
-                message_id = %message.id,
-                thread_id = %thread_id,
-                thread_state = ?thread_state,
-                "Checked thread state"
-            );
-
-            match thread_state {
-                ThreadState::Processing => {
-                    return Ok(SubmissionResult::error(
-                        "Turn in progress. Use /interrupt to cancel.",
-                    ));
-                }
-                ThreadState::AwaitingApproval => {
-                    return Ok(SubmissionResult::error(
-                        "Waiting for approval. Use /interrupt to cancel.",
-                    ));
-                }
-                ThreadState::Completed => {
-                    return Ok(SubmissionResult::error(
-                        "Thread completed. Use /thread new.",
-                    ));
-                }
-                ThreadState::Idle | ThreadState::Interrupted => {
-                    // Can proceed
-                }
-            }
-
            let messages = thread.messages();
            if let Some(strategy) = self.context_monitor.suggest_compaction(&messages) {
                let pct = self.context_monitor.usage_percent(&messages);
@@ -385,7 +414,7 @@ impl Agent {
            .get_mut(&thread_id)
            .ok_or_else(|| Error::from(crate::error::JobError::NotFound { id: thread_id }))?;

-        if thread.state() == ThreadState::Interrupted {
+        if thread.state == ThreadState::Interrupted {
            let _ = self
                .channels
                .send_status(
@@ -477,7 +506,8 @@ impl Agent {
                let tool_name = pending.tool_name.clone();
                let description = pending.description.clone();
                let parameters = pending.display_parameters.clone();
-                thread.await_approval(pending);
+                let allow_always = pending.allow_always;
+                thread.await_approval(*pending);
                let _ = self
                    .channels
                    .send_status(
@@ -487,6 +517,7 @@ impl Agent {
                            tool_name: tool_name.clone(),
                            description: description.clone(),
                            parameters: parameters.clone(),
+                            allow_always,
                        },
                        &message.metadata,
                    )
@@ -496,6 +527,7 @@ impl Agent {
                    tool_name,
                    description,
                    parameters,
+                    allow_always,
                })
            }
            Err(e) => {
@@ -758,7 +790,7 @@ impl Agent {
            .get_mut(&thread_id)
            .ok_or_else(|| Error::from(crate::error::JobError::NotFound { id: thread_id }))?;

-        match thread.state() {
+        match thread.state {
            ThreadState::Processing | ThreadState::AwaitingApproval => {
                thread.interrupt();
                Ok(SubmissionResult::ok_with_message("Interrupted."))
@@ -817,7 +849,7 @@ impl Agent {
            .get_mut(&thread_id)
            .ok_or_else(|| Error::from(crate::error::JobError::NotFound { id: thread_id }))?;
        thread.turns.clear();
-        thread.reset_to_idle();
+        thread.state = ThreadState::Idle;

        // Clear undo history too
        let undo_mgr = self.session_manager.get_undo_manager(thread_id).await;
@@ -844,11 +876,11 @@ impl Agent {
                .get_mut(&thread_id)
                .ok_or_else(|| Error::from(crate::error::JobError::NotFound { id: thread_id }))?;

-            if thread.state() != ThreadState::AwaitingApproval {
+            if thread.state != ThreadState::AwaitingApproval {
                // Stale or duplicate approval (tool already executed) — silently ignore.
                tracing::debug!(
                    %thread_id,
-                    state = ?thread.state(),
+                    state = ?thread.state,
                    "Ignoring stale approval: thread not in AwaitingApproval state"
                );
                return Ok(SubmissionResult::ok_with_message(""));
@@ -894,19 +926,18 @@ impl Agent {
                );
            }

-            // Reset thread state to processing (AwaitingApproval → Processing)
+            // Reset thread state to processing
            {
                let mut sess = session.lock().await;
-                if let Some(thread) = sess.threads.get_mut(&thread_id)
-                    && let Err(e) = thread.set_processing()
-                {
-                    tracing::warn!(%thread_id, "Invalid approval state transition: {}", e);
+                if let Some(thread) = sess.threads.get_mut(&thread_id) {
+                    thread.state = ThreadState::Processing;
                }
            }

            // Execute the approved tool and continue the loop
            let mut job_ctx =
-                JobContext::with_user(&message.user_id, "chat", "Interactive chat session");
+                JobContext::with_user(&message.user_id, "chat", "Interactive chat session")
+                    .with_requester_id(&message.sender_id);
            job_ctx.http_interceptor = self.deps.http_interceptor.clone();
            // Prefer a valid timezone from the approval message, fall back to the
            // resolved timezone stored when the approval was originally requested.
@@ -1041,28 +1072,31 @@ impl Agent {
                usize,
                crate::llm::ToolCall,
                Arc<dyn crate::tools::Tool>,
+                bool, // allow_always
            )> = None;

            for (idx, tc) in deferred_tool_calls.iter().enumerate() {
                if let Some(tool) = self.tools().get(&tc.name).await {
                    // Match dispatcher.rs: when auto_approve_tools is true, skip
                    // all approval checks (including ApprovalRequirement::Always).
-                    let needs_approval = if self.config.auto_approve_tools {
-                        false
+                    let (needs_approval, allow_always) = if self.config.auto_approve_tools {
+                        (false, true)
                    } else {
                        use crate::tools::ApprovalRequirement;
-                        match tool.requires_approval(&tc.arguments) {
+                        let requirement = tool.requires_approval(&tc.arguments);
+                        let needs = match requirement {
                            ApprovalRequirement::Never => false,
                            ApprovalRequirement::UnlessAutoApproved => {
                                let sess = session.lock().await;
                                !sess.is_tool_auto_approved(&tc.name)
                            }
                            ApprovalRequirement::Always => true,
-                        }
+                        };
+                        (needs, !matches!(requirement, ApprovalRequirement::Always))
                    };

                    if needs_approval {
-                        approval_needed = Some((idx, tc.clone(), tool));
+                        approval_needed = Some((idx, tc.clone(), tool, allow_always));
                        break; // remaining tools stay deferred
                    }
                }
@@ -1270,7 +1304,7 @@ impl Agent {
            }

            // Handle approval if a tool needed it
-            if let Some((approval_idx, tc, tool)) = approval_needed {
+            if let Some((approval_idx, tc, tool, allow_always)) = approval_needed {
                let new_pending = PendingApproval {
                    request_id: Uuid::new_v4(),
                    tool_name: tc.name.clone(),
@@ -1282,6 +1316,7 @@ impl Agent {
                    deferred_tool_calls: deferred_tool_calls[approval_idx + 1..].to_vec(),
                    // Carry forward the resolved timezone from the original pending approval
                    user_timezone: pending.user_timezone.clone(),
+                    allow_always,
                };

                let request_id = new_pending.request_id;
@@ -1305,6 +1340,7 @@ impl Agent {
                            tool_name: tool_name.clone(),
                            description: description.clone(),
                            parameters: parameters.clone(),
+                            allow_always,
                        },
                        &message.metadata,
                    )
@@ -1315,6 +1351,7 @@ impl Agent {
                    tool_name,
                    description,
                    parameters,
+                    allow_always,
                });
            }

@@ -1383,7 +1420,8 @@ impl Agent {
                    let tool_name = new_pending.tool_name.clone();
                    let description = new_pending.description.clone();
                    let parameters = new_pending.display_parameters.clone();
-                    thread.await_approval(new_pending);
+                    let allow_always = new_pending.allow_always;
+                    thread.await_approval(*new_pending);
                    let _ = self
                        .channels
                        .send_status(
@@ -1393,6 +1431,7 @@ impl Agent {
                                tool_name: tool_name.clone(),
                                description: description.clone(),
                                parameters: parameters.clone(),
+                                allow_always,
                            },
                            &message.metadata,
                        )
@@ -1402,6 +1441,7 @@ impl Agent {
                        tool_name,
                        description,
                        parameters,
+                        allow_always,
                    })
                }
                Err(e) => {
@@ -1898,4 +1938,104 @@ mod tests {
            created_at: chrono::Utc::now(),
        }
    }
+
+    #[tokio::test]
+    async fn test_awaiting_approval_rejection_includes_tool_context() {
+        // Test that when a thread is in AwaitingApproval state and receives a new message,
+        // process_user_input rejects it with a non-error status that includes tool context.
+        use crate::agent::session::{PendingApproval, Session, Thread, ThreadState};
+        use uuid::Uuid;
+
+        let session_id = Uuid::new_v4();
+        let thread_id = Uuid::new_v4();
+        let mut thread = Thread::with_id(thread_id, session_id);
+
+        // Set thread to AwaitingApproval with a pending tool approval
+        let pending = PendingApproval {
+            request_id: Uuid::new_v4(),
+            tool_name: "shell".to_string(),
+            parameters: serde_json::json!({"command": "echo hello"}),
+            display_parameters: serde_json::json!({"command": "[REDACTED]"}),
+            description: "Execute: echo hello".to_string(),
+            tool_call_id: "call_0".to_string(),
+            context_messages: vec![],
+            deferred_tool_calls: vec![],
+            user_timezone: None,
+            allow_always: false,
+        };
+        thread.await_approval(pending);
+
+        let mut session = Session::new("test-user");
+        session.threads.insert(thread_id, thread);
+
+        // Verify thread is in AwaitingApproval state
+        assert_eq!(
+            session.threads[&thread_id].state,
+            ThreadState::AwaitingApproval
+        );
+
+        let result = extract_approval_message(&session, thread_id);
+
+        // Verify result is an Ok with a message (not an Error)
+        match result {
+            Ok(Some(msg)) => {
+                // Should NOT start with "Error:"
+                assert!(
+                    !msg.to_lowercase().starts_with("error:"),
+                    "Approval rejection should not have 'Error:' prefix. Got: {}",
+                    msg
+                );
+
+                // Should contain "waiting for approval"
+                assert!(
+                    msg.to_lowercase().contains("waiting for approval"),
+                    "Should contain 'waiting for approval'. Got: {}",
+                    msg
+                );
+
+                // Should contain the tool name
+                assert!(
+                    msg.contains("shell"),
+                    "Should contain tool name 'shell'. Got: {}",
+                    msg
+                );
+
+                // Should contain the description (or truncated version)
+                assert!(
+                    msg.contains("echo hello"),
+                    "Should contain description 'echo hello'. Got: {}",
+                    msg
+                );
+            }
+            _ => panic!("Expected approval rejection message"),
+        }
+    }
+
+    // Helper function to extract the approval message without needing a full Agent instance
+    fn extract_approval_message(
+        session: &crate::agent::session::Session,
+        thread_id: Uuid,
+    ) -> Result<Option<String>, crate::error::Error> {
+        let thread = session.threads.get(&thread_id).ok_or_else(|| {
+            crate::error::Error::from(crate::error::JobError::NotFound { id: thread_id })
+        })?;
+
+        if thread.state == ThreadState::AwaitingApproval {
+            let approval_context = thread.pending_approval.as_ref().map(|a| {
+                let desc_preview =
+                    crate::agent::agent_loop::truncate_for_preview(&a.description, 80);
+                (a.tool_name.clone(), desc_preview)
+            });
+
+            let msg = match approval_context {
+                Some((tool_name, desc_preview)) => format!(
+                    "Waiting for approval: {tool_name} — {desc_preview}. Use /interrupt to cancel."
+                ),
+                None => "Waiting for approval. Use /interrupt to cancel.".to_string(),
+            };
+            Ok(Some(msg))
+        } else {
+            Ok(None)
+        }
+    }
 }
@@ -14,7 +14,6 @@ use crate::channels::web::log_layer::LogBroadcaster;
 use crate::config::Config;
 use crate::context::ContextManager;
 use crate::db::Database;
-use crate::event_bus::EventBus;
 use crate::extensions::ExtensionManager;
 use crate::hooks::HookRegistry;
 use crate::llm::{LlmProvider, RecordingLlm, SessionManager};
@@ -26,7 +25,7 @@ use crate::tools::ToolRegistry;
 use crate::tools::mcp::{McpProcessManager, McpSessionManager};
 use crate::tools::wasm::SharedCredentialRegistry;
 use crate::tools::wasm::WasmToolRuntime;
-use crate::workspace::{EmbeddingProvider, Workspace};
+use crate::workspace::{EmbeddingCacheConfig, EmbeddingProvider, Workspace};

 /// Fully initialized application components, ready for channel wiring
 /// and agent construction.
@@ -57,62 +56,7 @@ pub struct AppComponents {
    pub session: Arc<SessionManager>,
    pub catalog_entries: Vec<crate::extensions::RegistryEntry>,
    pub dev_loaded_tool_names: Vec<String>,
-    /// Unified event bus for all system events.
-    pub event_bus: EventBus,
-}
-
-impl AppComponents {
-    /// Verify that all components expected by the config are actually present.
-    ///
-    /// Logs warnings for any missing components. Called at end of `build_all()`
-    /// to catch wiring bugs early.
-    pub fn verify_readiness(&self) {
-        let mut warnings = Vec::new();
-
-        // Config cross-field validation
-        for issue in self.config.validate() {
-            warnings.push("config validation issue");
-            tracing::warn!(component = "startup_verification", "{}", issue);
-        }
-
-        // Note: db can legitimately be None if --no-db was passed.
-        // We only warn if workspace is expected but missing.
-
-        if self.workspace.is_none() && self.db.is_some() {
-            warnings.push("Workspace is None but database is available");
-        }
-
-        if self.wasm_tool_runtime.is_none() && self.config.wasm.enabled {
-            warnings.push("WASM runtime is None but config.wasm.enabled=true");
-        }
-
-        if self.extension_manager.is_none() {
-            warnings.push("Extension manager is None");
-        }
-
-        if self.skill_registry.is_none() && self.config.skills.enabled {
-            warnings.push("Skill registry is None but config.skills.enabled=true");
-        }
-
-        // Check tool registration
-        let missing_tools = self.tools.verify_expected_tools(&self.config);
-        for tool_name in &missing_tools {
-            warnings.push("missing expected tool");
-            tracing::warn!(
-                component = "startup_verification",
-                tool = tool_name,
-                "Expected tool not registered"
-            );
-        }
-
-        for warning in &warnings {
-            tracing::warn!(component = "startup_verification", "{}", warning);
-        }
-
-        if warnings.is_empty() {
-            tracing::debug!("All expected components initialized successfully");
-        }
-    }
+    pub builder: Option<Arc<dyn crate::tools::SoftwareBuilder>>,
 }

 /// Options that control optional init phases.
@@ -197,12 +141,14 @@ impl AppBuilder {
        self.handles = Some(handles);

        // Post-init: migrate disk config, reload config from DB, attach session, cleanup
-        if let Err(e) = crate::bootstrap::migrate_disk_to_db(db.as_ref(), "default").await {
+        if let Err(e) =
+            crate::bootstrap::migrate_disk_to_db(db.as_ref(), &self.config.owner_id).await
+        {
            tracing::warn!("Disk-to-DB settings migration failed: {}", e);
        }

        let toml_path = self.toml_path.as_deref();
-        match Config::from_db_with_toml(db.as_ref(), "default", toml_path).await {
+        match Config::from_db_with_toml(db.as_ref(), &self.config.owner_id, toml_path).await {
            Ok(db_config) => {
                self.config = db_config;
                tracing::debug!("Configuration reloaded from database");
@@ -215,7 +161,9 @@ impl AppBuilder {
            }
        }

-        self.session.attach_store(db.clone(), "default").await;
+        self.session
+            .attach_store(db.clone(), &self.config.owner_id)
+            .await;

        // Fire-and-forget housekeeping — no need to block startup.
        let db_cleanup = db.clone();
@@ -250,9 +198,10 @@ impl AppBuilder {
                let store: Option<&(dyn crate::db::SettingsStore + Sync)> =
                    self.db.as_ref().map(|db| db.as_ref() as _);
                let toml_path = self.toml_path.as_deref();
+                let owner_id = self.config.owner_id.clone();
                if let Err(e) = self
                    .config
-                    .re_resolve_llm(store, "default", toml_path)
+                    .re_resolve_llm(store, &owner_id, toml_path)
                    .await
                {
                    tracing::warn!(
@@ -281,15 +230,17 @@ impl AppBuilder {

        if let Some(ref secrets) = store {
            // Inject LLM API keys from encrypted storage
-            crate::config::inject_llm_keys_from_secrets(secrets.as_ref(), "default").await;
+            crate::config::inject_llm_keys_from_secrets(secrets.as_ref(), &self.config.owner_id)
+                .await;

            // Re-resolve only the LLM config with newly available keys.
            let store: Option<&(dyn crate::db::SettingsStore + Sync)> =
                self.db.as_ref().map(|db| db.as_ref() as _);
            let toml_path = self.toml_path.as_deref();
+            let owner_id = self.config.owner_id.clone();
            if let Err(e) = self
                .config
-                .re_resolve_llm(store, "default", toml_path)
+                .re_resolve_llm(store, &owner_id, toml_path)
                .await
            {
                tracing::warn!("Failed to re-resolve LLM config after secret injection: {e}");
@@ -330,6 +281,7 @@ impl AppBuilder {
            Arc<ToolRegistry>,
            Option<Arc<dyn EmbeddingProvider>>,
            Option<Arc<Workspace>>,
+            Option<Arc<dyn crate::tools::SoftwareBuilder>>,
        ),
        anyhow::Error,
    > {
@@ -361,10 +313,13 @@ impl AppBuilder {

        // Register memory tools if database is available
        let workspace = if let Some(ref db) = self.db {
-            let mut ws = Workspace::new_with_db("default", db.clone())
+            let emb_cache_config = EmbeddingCacheConfig {
+                max_entries: self.config.embeddings.cache_size,
+            };
+            let mut ws = Workspace::new_with_db(&self.config.owner_id, db.clone())
                .with_search_config(&self.config.search);
            if let Some(ref emb) = embeddings {
-                ws = ws.with_embeddings(emb.clone());
+                ws = ws.with_embeddings_cached(emb.clone(), emb_cache_config);
            }
            let ws = Arc::new(ws);
            tools.register_memory_tools(Arc::clone(&ws));
@@ -417,16 +372,19 @@ impl AppBuilder {
        }

        // Register builder tool if enabled
-        if self.config.builder.enabled
+        let builder = if self.config.builder.enabled
            && (self.config.agent.allow_local_tools || !self.config.sandbox.enabled)
        {
-            tools
+            let b = tools
                .register_builder_tool(llm.clone(), Some(self.config.builder.to_builder_config()))
                .await;
-            tracing::debug!("Builder mode enabled");
-        }
+            tracing::info!("Builder mode enabled");
+            Some(b)
+        } else {
+            None
+        };

-        Ok((safety, tools, embeddings, workspace))
+        Ok((safety, tools, embeddings, workspace, builder))
    }

    /// Phase 5: Load WASM tools, MCP servers, and create extension manager.
@@ -526,9 +484,10 @@ impl AppBuilder {
            let tools = Arc::clone(tools);
            let mcp_sm = Arc::clone(&mcp_session_manager);
            let pm = Arc::clone(&mcp_process_manager);
+            let owner_id = self.config.owner_id.clone();
            async move {
                let servers_result = if let Some(ref d) = db {
-                    load_mcp_servers_from_db(d.as_ref(), "default").await
+                    load_mcp_servers_from_db(d.as_ref(), &owner_id).await
                } else {
                    crate::tools::mcp::config::load_mcp_servers().await
                };
@@ -548,6 +507,7 @@ impl AppBuilder {
                            let secrets = secrets_store.clone();
                            let tools = Arc::clone(&tools);
                            let pm = Arc::clone(&pm);
+                            let owner_id = owner_id.clone();

                            join_set.spawn(async move {
                                let server_name = server.name.clone();
@@ -557,7 +517,7 @@ impl AppBuilder {
                                    &mcp_sm,
                                    &pm,
                                    secrets,
-                                    "default",
+                                    &owner_id,
                                )
                                .await
                                {
@@ -699,7 +659,7 @@ impl AppBuilder {
                self.config.wasm.tools_dir.clone(),
                self.config.channels.wasm_channels_dir.clone(),
                self.config.tunnel.public_url.clone(),
-                "default".to_string(),
+                self.config.owner_id.clone(),
                self.db.clone(),
                catalog_entries.clone(),
            ));
@@ -747,7 +707,7 @@ impl AppBuilder {
        } else {
            self.init_llm().await?
        };
-        let (safety, tools, embeddings, workspace) = self.init_tools(&llm).await?;
+        let (safety, tools, embeddings, workspace, builder) = self.init_tools(&llm).await?;

        // Create hook registry early so runtime extension activation can register hooks.
        let hooks = Arc::new(HookRegistry::new());
@@ -829,9 +789,6 @@ impl AppBuilder {
            (None, None)
        };

-        // Create unified event bus
-        let event_bus = EventBus::new();
-
        let context_manager = Arc::new(ContextManager::new(self.config.agent.max_parallel_jobs));
        let cost_guard = Arc::new(crate::agent::cost_guard::CostGuard::new(
            crate::agent::cost_guard::CostGuardConfig {
@@ -845,7 +802,7 @@ impl AppBuilder {
            tools.count()
        );

-        let components = AppComponents {
+        Ok(AppComponents {
            config: self.config,
            db: self.db,
            secrets_store: self.secrets_store,
@@ -870,12 +827,8 @@ impl AppBuilder {
            session: self.session,
            catalog_entries,
            dev_loaded_tool_names,
-            event_bus,
-        };
-
-        components.verify_readiness();
-
-        Ok(components)
+            builder,
+        })
    }
 }

@@ -67,14 +67,24 @@ pub struct IncomingMessage {
    pub id: Uuid,
    /// Channel this message came from.
    pub channel: String,
-    /// User identifier within the channel.
+    /// Storage/persistence scope for this interaction.
+    ///
+    /// For owner-capable channels this is the stable instance owner ID when the
+    /// configured owner is speaking; otherwise it can be a guest/sender-scoped
+    /// identifier to preserve isolation.
    pub user_id: String,
+    /// Stable instance owner scope for this IronClaw deployment.
+    pub owner_id: String,
+    /// Channel-specific sender/actor identifier.
+    pub sender_id: String,
    /// Optional display name.
    pub user_name: Option<String>,
    /// Message content.
    pub content: String,
    /// Thread/conversation ID for threaded conversations.
    pub thread_id: Option<String>,
+    /// Stable channel/chat/thread scope for this conversation.
+    pub conversation_scope_id: Option<String>,
    /// When the message was received.
    pub received_at: DateTime<Utc>,
    /// Channel-specific metadata.
@@ -84,9 +94,8 @@ pub struct IncomingMessage {
    /// File or media attachments on this message.
    pub attachments: Vec<IncomingAttachment>,
    /// Internal-only flag: message was generated inside the process (e.g. job
-    /// monitor) and must bypass the normal user-input pipeline.  This field is
-    /// **not** settable via `with_metadata()` — only trusted code paths inside
-    /// the binary can set it, preventing external channels from spoofing it.
+    /// monitor) and must bypass the normal user-input pipeline. This field is
+    /// not settable via metadata, so external channels cannot spoof it.
    pub(crate) is_internal: bool,
 }

@@ -97,13 +106,17 @@ impl IncomingMessage {
        user_id: impl Into<String>,
        content: impl Into<String>,
    ) -> Self {
+        let user_id = user_id.into();
        Self {
            id: Uuid::new_v4(),
            channel: channel.into(),
-            user_id: user_id.into(),
+            owner_id: user_id.clone(),
+            sender_id: user_id.clone(),
+            user_id,
            user_name: None,
            content: content.into(),
            thread_id: None,
+            conversation_scope_id: None,
            received_at: Utc::now(),
            metadata: serde_json::Value::Null,
            timezone: None,
@@ -114,7 +127,27 @@ impl IncomingMessage {

    /// Set the thread ID.
    pub fn with_thread(mut self, thread_id: impl Into<String>) -> Self {
-        self.thread_id = Some(thread_id.into());
+        let thread_id = thread_id.into();
+        self.conversation_scope_id = Some(thread_id.clone());
+        self.thread_id = Some(thread_id);
+        self
+    }
+
+    /// Set the stable owner scope for this message.
+    pub fn with_owner_id(mut self, owner_id: impl Into<String>) -> Self {
+        self.owner_id = owner_id.into();
+        self
+    }
+
+    /// Set the channel-specific sender/actor identifier.
+    pub fn with_sender_id(mut self, sender_id: impl Into<String>) -> Self {
+        self.sender_id = sender_id.into();
+        self
+    }
+
+    /// Set the conversation scope for this message.
+    pub fn with_conversation_scope(mut self, scope_id: impl Into<String>) -> Self {
+        self.conversation_scope_id = Some(scope_id.into());
        self
    }

@@ -147,6 +180,49 @@ impl IncomingMessage {
        self.is_internal = true;
        self
    }
+
+    /// Effective conversation scope, falling back to thread_id for legacy callers.
+    pub fn conversation_scope(&self) -> Option<&str> {
+        self.conversation_scope_id
+            .as_deref()
+            .or(self.thread_id.as_deref())
+    }
+
+    /// Best-effort routing target for proactive replies on the current channel.
+    pub fn routing_target(&self) -> Option<String> {
+        routing_target_from_metadata(&self.metadata).or_else(|| {
+            if self.sender_id.is_empty() {
+                None
+            } else {
+                Some(self.sender_id.clone())
+            }
+        })
+    }
+}
+
+/// Extract a channel-specific proactive routing target from message metadata.
+pub fn routing_target_from_metadata(metadata: &serde_json::Value) -> Option<String> {
+    metadata
+        .get("signal_target")
+        .and_then(|value| match value {
+            serde_json::Value::String(s) => Some(s.clone()),
+            serde_json::Value::Number(n) => Some(n.to_string()),
+            _ => None,
+        })
+        .or_else(|| {
+            metadata.get("chat_id").and_then(|value| match value {
+                serde_json::Value::String(s) => Some(s.clone()),
+                serde_json::Value::Number(n) => Some(n.to_string()),
+                _ => None,
+            })
+        })
+        .or_else(|| {
+            metadata.get("target").and_then(|value| match value {
+                serde_json::Value::String(s) => Some(s.clone()),
+                serde_json::Value::Number(n) => Some(n.to_string()),
+                _ => None,
+            })
+        })
 }

 /// Stream of incoming messages.
@@ -229,6 +305,11 @@ pub enum StatusUpdate {
        tool_name: String,
        description: String,
        parameters: serde_json::Value,
+        /// When `true`, the UI should offer an "always" option that auto-approves
+        /// future calls to this tool for the rest of the session.  When `false`
+        /// (i.e. `ApprovalRequirement::Always`), the tool must be approved every
+        /// time and the "always" button should be hidden.
+        allow_always: bool,
    },
    /// Extension needs user authentication (token or OAuth).
    AuthRequired {
@@ -133,7 +133,8 @@ impl HttpChannel {

 #[derive(Debug, Deserialize)]
 struct WebhookRequest {
-    /// User or client identifier (ignored, user is fixed by server config).
+    /// Optional caller or client identifier for sender-scoped routing.
+    /// The channel owner/storage scope remains fixed by server config.
    #[serde(default)]
    user_id: Option<String>,
    /// Message content.
@@ -403,12 +404,38 @@ async fn process_authenticated_request(
    state: Arc<HttpChannelState>,
    req: WebhookRequest,
 ) -> axum::response::Response {
-    let _ = req.user_id.as_ref().map(|user_id| {
-        tracing::debug!(
-            provided_user_id = %user_id,
-            "HTTP webhook request provided user_id, ignoring in favor of configured user_id"
-        );
-    });
+    let normalized_user_id = req
+        .user_id
+        .as_deref()
+        .map(str::trim)
+        .filter(|user_id| !user_id.is_empty());
+
+    match (req.user_id.as_deref(), normalized_user_id) {
+        (Some(raw_user_id), Some(user_id)) if raw_user_id != user_id => {
+            tracing::debug!(
+                provided_user_id = %raw_user_id,
+                normalized_sender_id = %user_id,
+                configured_owner_id = %state.user_id,
+                "HTTP webhook request provided user_id; trimming and using it as sender_id while keeping the configured owner scope"
+            );
+        }
+        (Some(user_id), Some(_)) => {
+            tracing::debug!(
+                provided_user_id = %user_id,
+                configured_owner_id = %state.user_id,
+                "HTTP webhook request provided user_id; using it as sender_id while keeping the configured owner scope"
+            );
+        }
+        (Some(raw_user_id), None) => {
+            tracing::debug!(
+                provided_user_id = %raw_user_id,
+                configured_owner_id = %state.user_id,
+                "HTTP webhook request provided a blank user_id; falling back to the configured owner scope for sender_id"
+            );
+        }
+        (None, None) => {}
+        (None, Some(_)) => unreachable!("normalized user_id requires a raw user_id"),
+    }

    if req.content.len() > MAX_CONTENT_BYTES {
        return (
@@ -514,11 +541,13 @@ async fn process_authenticated_request(
        Vec::new()
    };

-    let mut msg = IncomingMessage::new("http", &state.user_id, &req.content).with_metadata(
-        serde_json::json!({
+    let sender_id = normalized_user_id.unwrap_or(&state.user_id).to_string();
+    let mut msg = IncomingMessage::new("http", &state.user_id, &req.content)
+        .with_owner_id(&state.user_id)
+        .with_sender_id(sender_id)
+        .with_metadata(serde_json::json!({
            "wait_for_response": wait_for_response,
-        }),
-    );
+        }));

    if !attachments.is_empty() {
        msg = msg.with_attachments(attachments);
@@ -682,6 +711,7 @@ mod tests {
    use axum::body::Body;
    use axum::http::{HeaderValue, Request};
    use secrecy::SecretString;
+    use tokio_stream::StreamExt;
    use tower::ServiceExt;

    use super::*;
@@ -820,6 +850,70 @@ mod tests {
        assert_eq!(resp.status(), StatusCode::UNAUTHORIZED);
    }

+    #[tokio::test]
+    async fn webhook_blank_user_id_falls_back_to_owner_scope() {
+        let secret = "test-secret-123";
+        let channel = test_channel(Some(secret));
+        let mut stream = channel.start().await.unwrap();
+        let app = channel.routes();
+
+        let body = serde_json::json!({
+            "content": "hello",
+            "user_id": "   "
+        });
+        let body_bytes = serde_json::to_vec(&body).unwrap();
+        let signature = compute_signature(secret, &body_bytes);
+        let req = Request::builder()
+            .method("POST")
+            .uri("/webhook")
+            .header("content-type", "application/json")
+            .header("x-hub-signature-256", signature)
+            .body(Body::from(body_bytes))
+            .unwrap();
+
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(resp.status(), StatusCode::OK);
+
+        let msg = tokio::time::timeout(std::time::Duration::from_secs(1), stream.next())
+            .await
+            .expect("timed out waiting for webhook message")
+            .expect("stream should yield a webhook message");
+        assert_eq!(msg.sender_id, "http");
+        assert_eq!(msg.owner_id, "http");
+    }
+
+    #[tokio::test]
+    async fn webhook_user_id_is_trimmed_before_becoming_sender_id() {
+        let secret = "test-secret-123";
+        let channel = test_channel(Some(secret));
+        let mut stream = channel.start().await.unwrap();
+        let app = channel.routes();
+
+        let body = serde_json::json!({
+            "content": "hello",
+            "user_id": "  alice  "
+        });
+        let body_bytes = serde_json::to_vec(&body).unwrap();
+        let signature = compute_signature(secret, &body_bytes);
+        let req = Request::builder()
+            .method("POST")
+            .uri("/webhook")
+            .header("content-type", "application/json")
+            .header("x-hub-signature-256", signature)
+            .body(Body::from(body_bytes))
+            .unwrap();
+
+        let resp = app.oneshot(req).await.unwrap();
+        assert_eq!(resp.status(), StatusCode::OK);
+
+        let msg = tokio::time::timeout(std::time::Duration::from_secs(1), stream.next())
+            .await
+            .expect("timed out waiting for webhook message")
+            .expect("stream should yield a webhook message");
+        assert_eq!(msg.sender_id, "alice");
+        assert_eq!(msg.owner_id, "http");
+    }
+
    /// Regression test for issue #869: RwLock read guard was held across
    /// tx.send(msg).await in `process_message()`, blocking shutdown() from
    /// acquiring the write lock when the channel buffer was full.
@@ -239,6 +239,11 @@ impl ChannelManager {
    pub async fn get_channel(&self, name: &str) -> Option<Arc<dyn Channel>> {
        self.channels.read().await.get(name).cloned()
    }
+
+    /// Remove a channel from the manager.
+    pub async fn remove(&self, name: &str) -> Option<Arc<dyn Channel>> {
+        self.channels.write().await.remove(name)
+    }
 }

 impl Default for ChannelManager {
@@ -39,7 +39,7 @@ mod webhook_server;

 pub use channel::{
    AttachmentKind, Channel, ChannelSecretUpdater, IncomingAttachment, IncomingMessage,
-    MessageStream, OutgoingResponse, StatusUpdate,
+    MessageStream, OutgoingResponse, StatusUpdate, routing_target_from_metadata,
 };
 pub use http::{HttpChannel, HttpChannelState};
 pub use manager::ChannelManager;
@@ -1,16 +1,16 @@
-//! Channel trait implementation for channel-relay SSE streams.
+//! Channel trait implementation for channel-relay webhook callbacks.
 //!
-//! `RelayChannel` connects to a channel-relay service via SSE, converts
-//! incoming events to `IncomingMessage`s, and sends responses via the
-//! relay's provider-specific proxy API (Slack).
+//! `RelayChannel` receives events from channel-relay via HTTP POST callbacks
+//! (pushed through an mpsc channel by the webhook handler), converts them
+//! to `IncomingMessage`s, and sends responses via the relay's provider-specific
+//! proxy API (Slack).

 use std::collections::HashMap;
-use std::sync::Arc;

 use async_trait::async_trait;
-use tokio::sync::{RwLock, mpsc};
+use tokio::sync::mpsc;

-use crate::channels::relay::client::{RelayClient, RelayError};
+use crate::channels::relay::client::{ChannelEvent, RelayClient};
 use crate::channels::{Channel, IncomingMessage, MessageStream, OutgoingResponse, StatusUpdate};
 use crate::error::ChannelError;

@@ -39,44 +39,34 @@ impl RelayProvider {
    }
 }

-/// Channel implementation that connects to a channel-relay SSE stream.
+/// Channel implementation that receives events from channel-relay via webhook callbacks.
 pub struct RelayChannel {
    client: RelayClient,
    provider: RelayProvider,
-    stream_token: Arc<RwLock<String>>,
    team_id: String,
    instance_id: String,
-    user_id: String,
-    /// SSE stream long-poll timeout in seconds.
-    stream_timeout_secs: u64,
-    /// Initial exponential backoff in milliseconds.
-    backoff_initial_ms: u64,
-    /// Maximum exponential backoff in milliseconds.
-    backoff_max_ms: u64,
-    /// Handle to the reconnect task for clean shutdown.
-    reconnect_handle: RwLock<Option<tokio::task::JoinHandle<()>>>,
-    /// Handle to the SSE parser task for clean shutdown.
-    parser_handle: Arc<RwLock<Option<tokio::task::JoinHandle<()>>>>,
-    /// Maximum consecutive reconnect failures before giving up.
-    max_consecutive_failures: u64,
+    /// Sender side of the event channel — shared with the webhook handler.
+    event_tx: mpsc::Sender<ChannelEvent>,
+    /// Receiver side — taken once by `start()`.
+    event_rx: tokio::sync::Mutex<Option<mpsc::Receiver<ChannelEvent>>>,
 }

 impl RelayChannel {
    /// Create a new relay channel for Slack (default provider).
    pub fn new(
        client: RelayClient,
-        stream_token: String,
        team_id: String,
        instance_id: String,
-        user_id: String,
+        event_tx: mpsc::Sender<ChannelEvent>,
+        event_rx: mpsc::Receiver<ChannelEvent>,
    ) -> Self {
        Self::new_with_provider(
            client,
            RelayProvider::Slack,
-            stream_token,
            team_id,
            instance_id,
-            user_id,
+            event_tx,
+            event_rx,
        )
    }

@@ -84,44 +74,24 @@ impl RelayChannel {
    pub fn new_with_provider(
        client: RelayClient,
        provider: RelayProvider,
-        stream_token: String,
        team_id: String,
        instance_id: String,
-        user_id: String,
+        event_tx: mpsc::Sender<ChannelEvent>,
+        event_rx: mpsc::Receiver<ChannelEvent>,
    ) -> Self {
        Self {
            client,
            provider,
-            stream_token: Arc::new(RwLock::new(stream_token)),
            team_id,
            instance_id,
-            user_id,
-            stream_timeout_secs: 86400,
-            backoff_initial_ms: 1000,
-            backoff_max_ms: 60000,
-            reconnect_handle: RwLock::new(None),
-            parser_handle: Arc::new(RwLock::new(None)),
-            max_consecutive_failures: 50,
+            event_tx,
+            event_rx: tokio::sync::Mutex::new(Some(event_rx)),
        }
    }

-    /// Set backoff/timeout parameters from relay config values.
-    pub fn with_timeouts(
-        mut self,
-        stream_timeout_secs: u64,
-        backoff_initial_ms: u64,
-        backoff_max_ms: u64,
-    ) -> Self {
-        self.stream_timeout_secs = stream_timeout_secs;
-        self.backoff_initial_ms = backoff_initial_ms;
-        self.backoff_max_ms = backoff_max_ms;
-        self
-    }
-
-    /// Set the maximum number of consecutive reconnect failures before giving up.
-    pub fn with_max_failures(mut self, max: u64) -> Self {
-        self.max_consecutive_failures = max;
-        self
+    /// Get a clone of the event sender for wiring into the webhook endpoint.
+    pub fn event_sender(&self) -> mpsc::Sender<ChannelEvent> {
+        self.event_tx.clone()
    }

    /// Build a provider-appropriate proxy body for sending a message.
@@ -151,15 +121,9 @@ impl RelayChannel {
        team_id: &str,
        method: &str,
        body: serde_json::Value,
-    ) -> Result<serde_json::Value, RelayError> {
+    ) -> Result<serde_json::Value, crate::channels::relay::client::RelayError> {
        self.client
-            .proxy_provider(
-                self.provider.as_str(),
-                team_id,
-                method,
-                body,
-                Some(&self.instance_id),
-            )
+            .proxy_provider(self.provider.as_str(), team_id, method, body)
            .await
    }
 }
@@ -172,204 +136,82 @@ impl Channel for RelayChannel {

    async fn start(&self) -> Result<MessageStream, ChannelError> {
        let channel_name = self.name().to_string();
-        let token = self.stream_token.read().await.clone();
-        let (stream, initial_parser_handle) = self
-            .client
-            .connect_stream(&token, self.stream_timeout_secs)
-            .await
-            .map_err(|e| ChannelError::StartupFailed {
-                name: channel_name.clone(),
-                reason: e.to_string(),
-            })?;

-        *self.parser_handle.write().await = Some(initial_parser_handle);
+        // Take the receiver (can only start once)
+        let mut event_rx =
+            self.event_rx
+                .lock()
+                .await
+                .take()
+                .ok_or_else(|| ChannelError::StartupFailed {
+                    name: channel_name.clone(),
+                    reason: "RelayChannel already started".to_string(),
+                })?;

        let (tx, rx) = mpsc::channel(64);
-
-        // Spawn the stream reader + reconnect task
-        let client = self.client.clone();
-        let stream_token = Arc::clone(&self.stream_token);
-        let instance_id = self.instance_id.clone();
-        let user_id = self.user_id.clone();
-        let team_id = self.team_id.clone();
-        let stream_timeout_secs = self.stream_timeout_secs;
-        let backoff_initial_ms = self.backoff_initial_ms;
-        let backoff_max_ms = self.backoff_max_ms;
-        let max_consecutive_failures = self.max_consecutive_failures;
-        let parser_handle = Arc::clone(&self.parser_handle);
        let provider_str = self.provider.as_str().to_string();
        let relay_name = channel_name.clone();

-        let handle = tokio::spawn(async move {
-            use futures::StreamExt;
-
-            let mut current_stream = stream;
-            let mut backoff_ms = backoff_initial_ms;
-            let mut consecutive_failures: u64 = 0;
-
-            loop {
-                // Read events from the current stream
-                while let Some(event) = current_stream.next().await {
-                    // Reset backoff and failure count on successful event
-                    backoff_ms = backoff_initial_ms;
-                    consecutive_failures = 0;
-
-                    // Validate required fields
-                    if event.sender_id.is_empty()
-                        || event.channel_id.is_empty()
-                        || event.provider_scope.is_empty()
-                    {
-                        tracing::debug!(
-                            event_type = %event.event_type,
-                            sender_id = %event.sender_id,
-                            channel_id = %event.channel_id,
-                            "Relay: skipping event with missing required fields"
-                        );
-                        continue;
-                    }
-
-                    // Skip non-message events
-                    if !event.is_message() {
-                        tracing::debug!(
-                            event_type = %event.event_type,
-                            "Relay: skipping non-message event"
-                        );
-                        continue;
-                    }
-
-                    tracing::info!(
+        // Spawn a task that reads events from the webhook handler and converts to IncomingMessage
+        tokio::spawn(async move {
+            while let Some(event) = event_rx.recv().await {
+                // Validate required fields
+                if event.sender_id.is_empty()
+                    || event.channel_id.is_empty()
+                    || event.provider_scope.is_empty()
+                {
+                    tracing::debug!(
                        event_type = %event.event_type,
-                        sender = %event.sender_id,
-                        channel = %event.channel_id,
-                        provider = %provider_str,
-                        "Relay: received message from {}", provider_str
+                        sender_id = %event.sender_id,
+                        channel_id = %event.channel_id,
+                        "Relay: skipping event with missing required fields"
                    );
-
-                    let msg = IncomingMessage::new(&relay_name, &event.sender_id, event.text())
-                        .with_user_name(event.display_name())
-                        .with_metadata(serde_json::json!({
-                            "team_id": event.team_id(),
-                            "channel_id": event.channel_id,
-                            "sender_id": event.sender_id,
-                            "sender_name": event.display_name(),
-                            "event_type": event.event_type,
-                            "thread_id": event.thread_id,
-                            "provider": event.provider,
-                        }));
-
-                    let msg = if let Some(ref thread_id) = event.thread_id {
-                        msg.with_thread(thread_id)
-                    } else {
-                        msg.with_thread(&event.channel_id)
-                    };
-
-                    if tx.send(msg).await.is_err() {
-                        tracing::info!("Relay channel receiver dropped, stopping");
-                        return;
-                    }
+                    continue;
                }

-                // Stream ended, attempt reconnect with backoff
-                consecutive_failures += 1;
-                if consecutive_failures >= max_consecutive_failures {
-                    tracing::error!(
-                        channel = %relay_name,
-                        failures = consecutive_failures,
-                        "Relay channel giving up after {} consecutive failures",
-                        consecutive_failures
+                // Skip non-message events
+                if !event.is_message() {
+                    tracing::debug!(
+                        event_type = %event.event_type,
+                        "Relay: skipping non-message event"
                    );
-                    break;
+                    continue;
                }

-                tracing::warn!(
-                    backoff_ms = backoff_ms,
-                    failures = consecutive_failures,
-                    "Relay SSE stream ended, reconnecting..."
+                tracing::info!(
+                    event_type = %event.event_type,
+                    sender = %event.sender_id,
+                    channel = %event.channel_id,
+                    provider = %provider_str,
+                    "Relay: received message from {}", provider_str
                );
-                tokio::time::sleep(std::time::Duration::from_millis(backoff_ms)).await;
-                backoff_ms = (backoff_ms * 2).min(backoff_max_ms);

-                // Try to reconnect
-                let token = stream_token.read().await.clone();
-                match client.connect_stream(&token, stream_timeout_secs).await {
-                    Ok((new_stream, new_parser)) => {
-                        tracing::info!("Relay SSE stream reconnected");
-                        consecutive_failures = 0;
-                        backoff_ms = backoff_initial_ms;
-                        current_stream = new_stream;
-                        // Abort old parser before replacing
-                        if let Some(old) = parser_handle.write().await.take() {
-                            old.abort();
-                        }
-                        *parser_handle.write().await = Some(new_parser);
-                    }
-                    Err(RelayError::TokenExpired) => {
-                        // Attempt token renewal
-                        tracing::info!("Relay stream token expired, renewing...");
-                        match client.renew_token(&instance_id, &user_id).await {
-                            Ok(new_token) => {
-                                *stream_token.write().await = new_token.clone();
-                                match client.connect_stream(&new_token, stream_timeout_secs).await {
-                                    Ok((new_stream, new_parser)) => {
-                                        tracing::info!(
-                                            "Relay SSE stream reconnected with new token"
-                                        );
-                                        consecutive_failures = 0;
-                                        backoff_ms = backoff_initial_ms;
-                                        current_stream = new_stream;
-                                        if let Some(old) = parser_handle.write().await.take() {
-                                            old.abort();
-                                        }
-                                        *parser_handle.write().await = Some(new_parser);
-                                    }
-                                    Err(e) => {
-                                        tracing::error!(
-                                            error = %e,
-                                            "Failed to reconnect after token renewal"
-                                        );
-                                    }
-                                }
-                            }
-                            Err(e) => {
-                                tracing::error!(
-                                    error = %e,
-                                    "Failed to renew relay stream token"
-                                );
-                            }
-                        }
-                    }
-                    Err(e) => {
-                        tracing::error!(error = %e, "Failed to reconnect relay SSE stream");
-                    }
-                }
+                let msg = IncomingMessage::new(&relay_name, &event.sender_id, event.text())
+                    .with_user_name(event.display_name())
+                    .with_metadata(serde_json::json!({
+                        "team_id": event.team_id(),
+                        "channel_id": event.channel_id,
+                        "sender_id": event.sender_id,
+                        "sender_name": event.display_name(),
+                        "event_type": event.event_type,
+                        "thread_id": event.thread_id,
+                        "provider": event.provider,
+                    }));

-                // Check if the team is still valid (skip when team_id is unknown,
-                // e.g. when no DB store was available at activation time)
-                if !team_id.is_empty() {
-                    match client.list_connections(&instance_id).await {
-                        Ok(conns) => {
-                            let has_team =
-                                conns.iter().any(|c| c.team_id == team_id && c.connected);
-                            if !has_team {
-                                tracing::warn!(
-                                    team_id = %team_id,
-                                    "Team no longer connected, stopping relay channel"
-                                );
-                                return;
-                            }
-                        }
-                        Err(e) => {
-                            tracing::warn!(
-                                error = %e,
-                                "Could not verify team connection, will retry next iteration"
-                            );
-                        }
-                    }
+                let msg = if let Some(ref thread_id) = event.thread_id {
+                    msg.with_thread(thread_id)
+                } else {
+                    msg.with_thread(&event.channel_id)
+                };
+
+                if tx.send(msg).await.is_err() {
+                    tracing::info!("Relay channel receiver dropped, stopping");
+                    return;
                }
            }
-        });

-        *self.reconnect_handle.write().await = Some(handle);
+            tracing::info!("Relay event channel closed");
+        });

        let stream = tokio_stream::wrappers::ReceiverStream::new(rx);
        Ok(Box::pin(stream))
@@ -423,6 +265,7 @@ impl Channel for RelayChannel {
            tool_name,
            description,
            parameters,
+            allow_always: _,
        } = status
        else {
            return Ok(());
@@ -450,28 +293,24 @@ impl Channel for RelayChannel {
                name: self.name().to_string(),
                reason: "Missing channel_id for approval buttons".into(),
            })?;
-        let sender_id = metadata
-            .get("sender_id")
-            .and_then(|v| v.as_str())
-            .ok_or_else(|| ChannelError::SendFailed {
-                name: self.name().to_string(),
-                reason: "Missing sender_id for approval buttons".into(),
-            })?;
        let thread_id = metadata.get("thread_id").and_then(|v| v.as_str());
        let team_id = metadata
            .get("team_id")
            .and_then(|v| v.as_str())
            .unwrap_or(&self.team_id);

-        // Button value payload (Slack limits button values to 2000 chars;
-        // safe with typical UUIDs but documented here as a constraint)
+        // Register server-side approval record and get opaque token.
+        // The button value contains ONLY the token — no routing fields.
+        let approval_token = self
+            .client
+            .create_approval(team_id, channel_id, thread_id, &request_id)
+            .await
+            .map_err(|e| ChannelError::SendFailed {
+                name: self.name().to_string(),
+                reason: format!("Failed to register approval: {e}"),
+            })?;
        let value_payload = serde_json::json!({
-            "instance_id": self.instance_id,
-            "team_id": team_id,
-            "channel_id": channel_id,
-            "thread_ts": thread_id,
-            "request_id": request_id,
-            "sender_id": sender_id,
+            "approval_token": approval_token,
        });
        let value_str = value_payload.to_string();

@@ -582,12 +421,8 @@ impl Channel for RelayChannel {
    }

    async fn shutdown(&self) -> Result<(), ChannelError> {
-        if let Some(handle) = self.reconnect_handle.write().await.take() {
-            handle.abort();
-        }
-        if let Some(handle) = self.parser_handle.write().await.take() {
-            handle.abort();
-        }
+        // Relay cleanup is driven by the extension manager dropping the shared
+        // sender and removing the channel from the channel manager.
        Ok(())
    }
 }
@@ -605,27 +440,20 @@ mod tests {
        .expect("client")
    }

+    fn make_channel() -> RelayChannel {
+        let (tx, rx) = mpsc::channel(64);
+        RelayChannel::new(test_client(), "T123".into(), "inst1".into(), tx, rx)
+    }
+
    #[test]
    fn relay_channel_name() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
+        let channel = make_channel();
        assert_eq!(channel.name(), DEFAULT_RELAY_NAME);
    }

    #[test]
    fn conversation_context_extracts_metadata() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
+        let channel = make_channel();

        let metadata = serde_json::json!({
            "sender_name": "bob",
@@ -640,8 +468,6 @@ mod tests {

    #[test]
    fn metadata_shape_includes_event_type_and_sender_name() {
-        // Regression: metadata JSON must include event_type and sender_name
-        // for downstream routing (DM vs channel) and conversation_context().
        let metadata = serde_json::json!({
            "team_id": "T123",
            "channel_id": "C456",
@@ -651,43 +477,19 @@ mod tests {
            "thread_id": null,
            "provider": "slack",
        });
-        // event_type must be present for DM-vs-channel routing
        assert_eq!(
            metadata.get("event_type").and_then(|v| v.as_str()),
            Some("direct_message")
        );
-        // sender_name must be present for conversation_context
        assert_eq!(
            metadata.get("sender_name").and_then(|v| v.as_str()),
            Some("alice")
        );
    }

-    #[test]
-    fn with_timeouts_sets_values() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        )
-        .with_timeouts(43200, 2000, 120000);
-
-        assert_eq!(channel.stream_timeout_secs, 43200);
-        assert_eq!(channel.backoff_initial_ms, 2000);
-        assert_eq!(channel.backoff_max_ms, 120000);
-    }
-
    #[test]
    fn build_send_body_slack() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
+        let channel = make_channel();
        let (method, body) = channel.build_send_body("C456", "hello", Some("1234567.890"));
        assert_eq!(method, "chat.postMessage");
        assert_eq!(body["channel"], "C456");
@@ -695,72 +497,95 @@ mod tests {
        assert_eq!(body["thread_ts"], "1234567.890");
    }

-    #[test]
-    fn parser_handle_is_shared_arc() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
-        // parser_handle should be an Arc — cloning should give a second reference
-        let handle_clone = Arc::clone(&channel.parser_handle);
-        // Both point to the same allocation
-        assert!(Arc::ptr_eq(&channel.parser_handle, &handle_clone));
+    #[tokio::test]
+    async fn start_processes_events() {
+        let (tx, rx) = mpsc::channel(64);
+        let channel =
+            RelayChannel::new(test_client(), "T123".into(), "inst1".into(), tx.clone(), rx);
+
+        let mut stream = channel.start().await.unwrap();
+
+        // Send an event
+        tx.send(ChannelEvent {
+            id: "1".into(),
+            event_type: "message".into(),
+            provider: "slack".into(),
+            provider_scope: "T123".into(),
+            channel_id: "C456".into(),
+            sender_id: "U789".into(),
+            sender_name: Some("alice".into()),
+            content: Some("hello".into()),
+            thread_id: None,
+            raw: serde_json::Value::Null,
+            timestamp: None,
+        })
+        .await
+        .unwrap();
+
+        use futures::StreamExt;
+        let msg = tokio::time::timeout(std::time::Duration::from_secs(1), stream.next())
+            .await
+            .unwrap()
+            .unwrap();
+
+        assert_eq!(msg.content, "hello");
+        assert_eq!(msg.user_id, "U789");
    }

-    #[test]
-    fn with_max_failures_sets_value() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        )
-        .with_max_failures(10);
+    #[tokio::test]
+    async fn start_skips_non_message_events() {
+        let (tx, rx) = mpsc::channel(64);
+        let channel =
+            RelayChannel::new(test_client(), "T123".into(), "inst1".into(), tx.clone(), rx);

-        assert_eq!(channel.max_consecutive_failures, 10);
-    }
+        let mut stream = channel.start().await.unwrap();

-    #[test]
-    fn default_max_failures_is_50() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
-        assert_eq!(channel.max_consecutive_failures, 50);
-    }
+        // Send a non-message event (should be skipped)
+        tx.send(ChannelEvent {
+            id: "1".into(),
+            event_type: "reaction".into(),
+            provider: "slack".into(),
+            provider_scope: "T123".into(),
+            channel_id: "C456".into(),
+            sender_id: "U789".into(),
+            sender_name: None,
+            content: None,
+            thread_id: None,
+            raw: serde_json::Value::Null,
+            timestamp: None,
+        })
+        .await
+        .unwrap();

-    #[test]
-    fn empty_team_id_accepted_at_construction() {
-        // Regression: empty team_id (when no DB store is available) must not
-        // prevent channel construction or cause immediate shutdown.
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            String::new(), // empty team_id
-            "inst1".into(),
-            "user1".into(),
-        );
-        assert_eq!(channel.team_id, "");
-        // The reconnect loop now skips team validation when team_id is empty,
-        // so the channel remains alive.
+        // Send a real message
+        tx.send(ChannelEvent {
+            id: "2".into(),
+            event_type: "message".into(),
+            provider: "slack".into(),
+            provider_scope: "T123".into(),
+            channel_id: "C456".into(),
+            sender_id: "U789".into(),
+            sender_name: None,
+            content: Some("real message".into()),
+            thread_id: None,
+            raw: serde_json::Value::Null,
+            timestamp: None,
+        })
+        .await
+        .unwrap();
+
+        use futures::StreamExt;
+        let msg = tokio::time::timeout(std::time::Duration::from_secs(1), stream.next())
+            .await
+            .unwrap()
+            .unwrap();
+
+        assert_eq!(msg.content, "real message");
    }

    #[tokio::test]
    async fn test_send_status_non_approval_is_noop() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
+        let channel = make_channel();
        let metadata = serde_json::json!({});
        let result = channel
            .send_status(
@@ -775,13 +600,7 @@ mod tests {

    #[tokio::test]
    async fn test_send_status_approval_non_dm_skips() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
+        let channel = make_channel();
        let metadata = serde_json::json!({
            "event_type": "message",
            "channel_id": "C456",
@@ -794,6 +613,7 @@ mod tests {
                    tool_name: "shell".into(),
                    description: "run command".into(),
                    parameters: serde_json::json!({}),
+                    allow_always: true,
                },
                &metadata,
            )
@@ -804,13 +624,7 @@ mod tests {

    #[tokio::test]
    async fn test_send_status_approval_dm_missing_channel_id_errors() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
+        let channel = make_channel();
        let metadata = serde_json::json!({
            "event_type": "direct_message",
            "sender_id": "U789",
@@ -822,6 +636,7 @@ mod tests {
                    tool_name: "shell".into(),
                    description: "run command".into(),
                    parameters: serde_json::json!({}),
+                    allow_always: true,
                },
                &metadata,
            )
@@ -835,14 +650,8 @@ mod tests {
    }

    #[tokio::test]
-    async fn test_send_status_approval_dm_missing_sender_id_errors() {
-        let channel = RelayChannel::new(
-            test_client(),
-            "token".into(),
-            "T123".into(),
-            "inst1".into(),
-            "user1".into(),
-        );
+    async fn test_send_status_approval_dm_without_sender_id_is_ok() {
+        let channel = make_channel();
        let metadata = serde_json::json!({
            "event_type": "direct_message",
            "channel_id": "C456",
@@ -854,6 +663,7 @@ mod tests {
                    tool_name: "shell".into(),
                    description: "run command".into(),
                    parameters: serde_json::json!({}),
+                    allow_always: true,
                },
                &metadata,
            )
@@ -861,8 +671,8 @@ mod tests {
        assert!(result.is_err());
        let err = result.unwrap_err().to_string();
        assert!(
-            err.contains("sender_id"),
-            "expected sender_id error, got: {err}"
+            !err.contains("sender_id"),
+            "sender_id should not be required anymore, got: {err}"
        );
    }
 }
@@ -1,15 +1,10 @@
 //! HTTP client for the channel-relay service.
 //!
 //! Wraps reqwest for all channel-relay API calls: OAuth initiation,
-//! SSE streaming, token renewal, and Slack API proxy.
+//! approvals, signing-secret fetch, and Slack API proxy.

-use std::pin::Pin;
-use std::task::{Context, Poll};
-
-use futures::Stream;
 use secrecy::{ExposeSecret, SecretString};
 use serde::{Deserialize, Serialize};
-use tokio::sync::mpsc;

 /// Known relay event types.
 pub mod event_types {
@@ -18,7 +13,7 @@ pub mod event_types {
    pub const MENTION: &str = "mention";
 }

-/// A parsed SSE event from the channel-relay stream.
+/// A parsed event from the channel-relay webhook callback.
 ///
 /// Field names match the channel-relay `ChannelEvent` struct exactly.
 #[derive(Debug, Clone, Serialize, Deserialize)]
@@ -123,21 +118,19 @@ impl RelayClient {
    ///
    /// Calls `GET /oauth/slack/auth` with `redirect(Policy::none())` and
    /// returns the `Location` header (Slack OAuth URL) without following it.
-    pub async fn initiate_oauth(
-        &self,
-        instance_id: &str,
-        user_id: &str,
-        callback_url: &str,
-    ) -> Result<String, RelayError> {
+    /// Initiate Slack OAuth. Channel-relay derives all URLs from the trusted
+    /// instance_url in chat-api. IronClaw only passes an optional CSRF nonce
+    /// for validating the callback — no URLs.
+    pub async fn initiate_oauth(&self, state_nonce: Option<&str>) -> Result<String, RelayError> {
+        let mut query: Vec<(&str, &str)> = vec![];
+        if let Some(nonce) = state_nonce {
+            query.push(("state_nonce", nonce));
+        }
        let resp = self
            .http
            .get(format!("{}/oauth/slack/auth", self.base_url))
-            .header("X-API-Key", self.api_key.expose_secret())
-            .query(&[
-                ("instance_id", instance_id),
-                ("user_id", user_id),
-                ("callback", callback_url),
-            ])
+            .bearer_auth(self.api_key.expose_secret())
+            .query(&query)
            .send()
            .await
            .map_err(|e| RelayError::Network(e.to_string()))?;
@@ -173,104 +166,69 @@ impl RelayClient {
        }
    }

-    /// Connect to the SSE event stream.
+    /// Register a pending approval and return the opaque approval token.
    ///
-    /// Returns a stream of parsed `ChannelEvent`s and the `JoinHandle` of the
-    /// background SSE parser task. The caller is responsible for reconnection
-    /// logic on stream end/error and for aborting the handle on shutdown.
-    pub async fn connect_stream(
+    /// Calls `POST /approvals` with the target team/channel/request identifiers.
+    /// The returned token is embedded in Slack button values instead of routing fields.
+    /// The relay derives the authorized approver from the connection's authed_user_id.
+    pub async fn create_approval(
        &self,
-        stream_token: &str,
-        stream_timeout_secs: u64,
-    ) -> Result<(ChannelEventStream, tokio::task::JoinHandle<()>), RelayError> {
-        let resp = self
-            .http
-            .get(format!("{}/stream", self.base_url))
-            .query(&[("token", stream_token)])
-            .timeout(std::time::Duration::from_secs(stream_timeout_secs))
-            .send()
-            .await
-            .map_err(|e| RelayError::Network(e.to_string()))?;
-
-        let status = resp.status();
-        if status == reqwest::StatusCode::UNAUTHORIZED {
-            return Err(RelayError::TokenExpired);
-        }
-        if !status.is_success() {
-            let body = resp.text().await.unwrap_or_default();
-            return Err(RelayError::Api {
-                status: status.as_u16(),
-                message: body,
-            });
-        }
-
-        // Spawn a background task that reads the SSE stream and sends parsed events
-        let (tx, rx) = mpsc::channel(64);
-        let byte_stream = resp.bytes_stream();
-        let handle = tokio::spawn(parse_sse_stream(byte_stream, tx));
-
-        Ok((ChannelEventStream { rx }, handle))
-    }
-
-    /// Renew an expired stream token.
-    ///
-    /// Calls `POST /stream/renew` with API key auth, returns a new stream token.
-    pub async fn renew_token(
-        &self,
-        instance_id: &str,
-        user_id: &str,
+        team_id: &str,
+        channel_id: &str,
+        thread_ts: Option<&str>,
+        request_id: &str,
    ) -> Result<String, RelayError> {
+        let mut body = serde_json::json!({
+            "team_id": team_id,
+            "channel_id": channel_id,
+            "request_id": request_id,
+        });
+        if let Some(ts) = thread_ts {
+            body["thread_ts"] = serde_json::Value::String(ts.to_string());
+        }
+
        let resp = self
            .http
-            .post(format!("{}/stream/renew", self.base_url))
-            .header("X-API-Key", self.api_key.expose_secret())
-            .json(&serde_json::json!({
-                "instance_id": instance_id,
-                "user_id": user_id,
-            }))
+            .post(format!("{}/approvals", self.base_url))
+            .bearer_auth(self.api_key.expose_secret())
+            .json(&body)
            .send()
            .await
            .map_err(|e| RelayError::Network(e.to_string()))?;

-        let status = resp.status();
-        if !status.is_success() {
+        if !resp.status().is_success() {
+            let status = resp.status().as_u16();
            let body = resp.text().await.unwrap_or_default();
            return Err(RelayError::Api {
-                status: status.as_u16(),
+                status,
                message: body,
            });
        }

-        let body: serde_json::Value = resp
+        let result: serde_json::Value = resp
            .json()
            .await
            .map_err(|e| RelayError::Protocol(e.to_string()))?;
-        body.get("stream_token")
-            .or_else(|| body.get("token"))
+
+        result
+            .get("approval_token")
            .and_then(|v| v.as_str())
            .map(|s| s.to_string())
-            .ok_or_else(|| RelayError::Protocol("Response missing stream_token field".to_string()))
+            .ok_or_else(|| RelayError::Protocol("missing approval_token in response".to_string()))
    }

-    /// Proxy an API call through channel-relay for any provider.
-    ///
-    /// Calls `POST /proxy/{provider}/{method}?team_id=X&instance_id=Y` with the given JSON body.
    pub async fn proxy_provider(
        &self,
        provider: &str,
        team_id: &str,
        method: &str,
        body: serde_json::Value,
-        instance_id: Option<&str>,
    ) -> Result<serde_json::Value, RelayError> {
-        let mut query: Vec<(&str, &str)> = vec![("team_id", team_id)];
-        if let Some(iid) = instance_id {
-            query.push(("instance_id", iid));
-        }
+        let query: Vec<(&str, &str)> = vec![("team_id", team_id)];
        let resp = self
            .http
            .post(format!("{}/proxy/{}/{}", self.base_url, provider, method))
-            .header("X-API-Key", self.api_key.expose_secret())
+            .bearer_auth(self.api_key.expose_secret())
            .query(&query)
            .json(&body)
            .send()
@@ -291,12 +249,58 @@ impl RelayClient {
            .map_err(|e| RelayError::Protocol(e.to_string()))
    }

+    /// Fetch the per-instance callback signing secret from channel-relay.
+    ///
+    /// Calls `GET /relay/signing-secret` (authenticated) and returns the decoded
+    /// 32-byte secret. Called once at activation time; the result is cached in the
+    /// extension manager so subsequent calls to `relay_signing_secret()` use it.
+    pub async fn get_signing_secret(&self, team_id: &str) -> Result<Vec<u8>, RelayError> {
+        let resp = self
+            .http
+            .get(format!("{}/relay/signing-secret", self.base_url))
+            .bearer_auth(self.api_key.expose_secret())
+            .query(&[("team_id", team_id)])
+            .send()
+            .await
+            .map_err(|e| RelayError::Network(e.to_string()))?;
+
+        if !resp.status().is_success() {
+            let status = resp.status().as_u16();
+            let body = resp.text().await.unwrap_or_default();
+            return Err(RelayError::Api {
+                status,
+                message: body,
+            });
+        }
+
+        let body: serde_json::Value = resp
+            .json()
+            .await
+            .map_err(|e| RelayError::Protocol(e.to_string()))?;
+
+        body.get("signing_secret")
+            .and_then(|v| v.as_str())
+            .ok_or_else(|| RelayError::Protocol("missing signing_secret in response".to_string()))
+            .and_then(|raw| {
+                let decoded = hex::decode(raw).map_err(|e| {
+                    RelayError::Protocol(format!("invalid signing_secret hex: {e}"))
+                })?;
+                if decoded.len() != 32 {
+                    return Err(RelayError::Protocol(format!(
+                        "invalid signing_secret length: expected 32 bytes, got {}",
+                        decoded.len()
+                    )));
+                }
+                Ok(decoded)
+            })
+    }
+
    /// List active connections for an instance.
    pub async fn list_connections(&self, instance_id: &str) -> Result<Vec<Connection>, RelayError> {
        let resp = self
            .http
            .get(format!("{}/connections", self.base_url))
-            .header("X-API-Key", self.api_key.expose_secret())
+            .bearer_auth(self.api_key.expose_secret())
            .query(&[("instance_id", instance_id)])
            .send()
            .await
@@ -317,91 +321,6 @@ impl RelayClient {
    }
 }

-/// Async stream of parsed channel events from SSE.
-pub struct ChannelEventStream {
-    rx: mpsc::Receiver<ChannelEvent>,
-}
-
-impl Stream for ChannelEventStream {
-    type Item = ChannelEvent;
-
-    fn poll_next(mut self: Pin<&mut Self>, cx: &mut Context<'_>) -> Poll<Option<Self::Item>> {
-        self.rx.poll_recv(cx)
-    }
-}
-
-/// Parse SSE format from a reqwest bytes stream.
-///
-/// SSE format:
-/// ```text
-/// event: message
-/// data: {"key": "value"}
-///
-/// ```
-/// Blank line terminates an event.
-async fn parse_sse_stream(
-    byte_stream: impl futures::Stream<Item = Result<bytes::Bytes, reqwest::Error>> + Send + 'static,
-    tx: mpsc::Sender<ChannelEvent>,
-) {
-    use futures::StreamExt;
-
-    let mut buffer = Vec::<u8>::new();
-    let mut event_type = String::new();
-    let mut data_lines = Vec::new();
-
-    let mut byte_stream = std::pin::pin!(byte_stream);
-    while let Some(chunk_result) = byte_stream.next().await {
-        let chunk = match chunk_result {
-            Ok(c) => c,
-            Err(e) => {
-                tracing::debug!(error = %e, "SSE stream chunk error");
-                break;
-            }
-        };
-
-        buffer.extend_from_slice(&chunk);
-
-        // Process complete lines (decode UTF-8 only on full lines to avoid
-        // corruption when multi-byte characters span chunk boundaries)
-        while let Some(newline_pos) = buffer.iter().position(|&b| b == b'\n') {
-            let line = String::from_utf8_lossy(&buffer[..newline_pos])
-                .trim_end_matches('\r')
-                .to_string();
-            buffer.drain(..=newline_pos);
-
-            if line.is_empty() {
-                // Blank line = end of event
-                if !data_lines.is_empty() {
-                    let data = data_lines.join("\n");
-                    if let Ok(mut event) = serde_json::from_str::<ChannelEvent>(&data) {
-                        if event.event_type.is_empty() && !event_type.is_empty() {
-                            event.event_type = event_type.clone();
-                        }
-                        if tx.send(event).await.is_err() {
-                            return; // receiver dropped
-                        }
-                    } else {
-                        tracing::debug!(
-                            event_type = %event_type,
-                            data_len = data.len(),
-                            "Failed to parse SSE event data as ChannelEvent"
-                        );
-                    }
-                }
-                event_type.clear();
-                data_lines.clear();
-            } else if let Some(value) = line.strip_prefix("event:") {
-                event_type = value.trim().to_string();
-            } else if let Some(value) = line.strip_prefix("data:") {
-                data_lines.push(value.trim().to_string());
-            }
-            // Ignore other fields (id:, retry:, comments)
-        }
-    }
-
-    tracing::debug!("SSE stream ended");
-}
-
 /// Errors from relay client operations.
 #[derive(Debug, thiserror::Error)]
 pub enum RelayError {
@@ -413,9 +332,6 @@ pub enum RelayError {

    #[error("Protocol error: {0}")]
    Protocol(String),
-
-    #[error("Stream token expired")]
-    TokenExpired,
 }

 #[cfg(test)]
@@ -494,9 +410,6 @@ mod tests {
            message: "unauthorized".into(),
        };
        assert_eq!(err.to_string(), "API error (HTTP 401): unauthorized");
-
-        let err = RelayError::TokenExpired;
-        assert_eq!(err.to_string(), "Stream token expired");
    }

    #[test]
@@ -518,32 +431,4 @@ mod tests {
        assert!(make(event_types::DIRECT_MESSAGE).is_message());
        assert!(make(event_types::MENTION).is_message());
    }
-
-    #[tokio::test]
-    async fn parse_sse_handles_multibyte_utf8_across_chunks() {
-        // The crab emoji (🦀) is 4 bytes: [0xF0, 0x9F, 0xA6, 0x80].
-        // Split it across two chunks to verify no U+FFFD corruption.
-        let event_json = r#"{"event_type":"message","content":"hello 🦀 world","provider_scope":"T1","channel_id":"C1","sender_id":"U1"}"#;
-        let full = format!("event: message\ndata: {}\n\n", event_json);
-        let bytes = full.as_bytes();
-
-        // Find the crab emoji and split mid-character
-        let crab_pos = bytes
-            .windows(4)
-            .position(|w| w == [0xF0, 0x9F, 0xA6, 0x80])
-            .expect("crab emoji not found");
-        let split_at = crab_pos + 2; // split in the middle of the 4-byte emoji
-
-        let chunk1 = bytes::Bytes::copy_from_slice(&bytes[..split_at]);
-        let chunk2 = bytes::Bytes::copy_from_slice(&bytes[split_at..]);
-
-        let chunks: Vec<Result<bytes::Bytes, reqwest::Error>> = vec![Ok(chunk1), Ok(chunk2)];
-        let stream = futures::stream::iter(chunks);
-
-        let (tx, mut rx) = mpsc::channel(8);
-        parse_sse_stream(stream, tx).await;
-
-        let event = rx.recv().await.expect("should receive event");
-        assert_eq!(event.text(), "hello 🦀 world");
-    }
 }
@@ -1,12 +1,13 @@
 //! Channel-relay integration for connecting to external messaging platforms
 //! (Slack) via the channel-relay service.
 //!
-//! The relay service handles OAuth, credential storage, webhook ingestion,
-//! and SSE event streaming. IronClaw consumes the SSE stream and sends
-//! messages via the relay's proxy API.
+//! The relay service handles OAuth, credential storage, and webhook ingestion.
+//! IronClaw receives events via webhook callbacks and sends messages via the
+//! relay's proxy API.

 pub mod channel;
 pub mod client;
+pub mod webhook;

 pub use channel::{DEFAULT_RELAY_NAME, RelayChannel};
 pub use client::RelayClient;
@@ -0,0 +1,66 @@
+//! Shared relay webhook signature verification helpers.
+
+use hmac::{Hmac, Mac};
+use sha2::Sha256;
+
+type HmacSha256 = Hmac<Sha256>;
+
+/// Verify a relay callback HMAC signature.
+pub fn verify_relay_signature(
+    secret: &[u8],
+    timestamp: &str,
+    body: &[u8],
+    signature: &str,
+) -> bool {
+    verify_signature(secret, timestamp, body, signature)
+}
+
+fn verify_signature(secret: &[u8], timestamp: &str, body: &[u8], signature: &str) -> bool {
+    let mut mac = match HmacSha256::new_from_slice(secret) {
+        Ok(m) => m,
+        Err(_) => return false,
+    };
+    mac.update(timestamp.as_bytes());
+    mac.update(b".");
+    mac.update(body);
+    let expected = format!("sha256={}", hex::encode(mac.finalize().into_bytes()));
+    subtle::ConstantTimeEq::ct_eq(expected.as_bytes(), signature.as_bytes()).into()
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    fn make_signature(secret: &[u8], timestamp: &str, body: &[u8]) -> String {
+        let mut mac = HmacSha256::new_from_slice(secret).unwrap();
+        mac.update(timestamp.as_bytes());
+        mac.update(b".");
+        mac.update(body);
+        format!("sha256={}", hex::encode(mac.finalize().into_bytes()))
+    }
+
+    #[test]
+    fn verify_valid_signature() {
+        let secret = b"test-secret";
+        let body = b"hello";
+        let ts = "1234567890";
+        let sig = make_signature(secret, ts, body);
+        assert!(verify_signature(secret, ts, body, &sig));
+    }
+
+    #[test]
+    fn verify_wrong_secret_fails() {
+        let body = b"hello";
+        let ts = "1234567890";
+        let sig = make_signature(b"correct", ts, body);
+        assert!(!verify_signature(b"wrong", ts, body, &sig));
+    }
+
+    #[test]
+    fn verify_tampered_body_fails() {
+        let secret = b"secret";
+        let ts = "1234567890";
+        let sig = make_signature(secret, ts, b"original");
+        assert!(!verify_signature(secret, ts, b"tampered", &sig));
+    }
+}
@@ -200,6 +200,8 @@ fn format_json_params(params: &serde_json::Value, indent: &str) -> String {

 /// REPL channel with line editing and markdown rendering.
 pub struct ReplChannel {
+    /// Stable owner scope for this REPL instance.
+    user_id: String,
    /// Optional single message to send (for -m flag).
    single_message: Option<String>,
    /// Debug mode flag (shared with input thread).
@@ -213,7 +215,13 @@ pub struct ReplChannel {
 impl ReplChannel {
    /// Create a new REPL channel.
    pub fn new() -> Self {
+        Self::with_user_id("default")
+    }
+
+    /// Create a new REPL channel for a specific owner scope.
+    pub fn with_user_id(user_id: impl Into<String>) -> Self {
        Self {
+            user_id: user_id.into(),
            single_message: None,
            debug_mode: Arc::new(AtomicBool::new(false)),
            is_streaming: Arc::new(AtomicBool::new(false)),
@@ -223,7 +231,13 @@ impl ReplChannel {

    /// Create a REPL channel that sends a single message and exits.
    pub fn with_message(message: String) -> Self {
+        Self::with_message_for_user("default", message)
+    }
+
+    /// Create a REPL channel that sends a single message for a specific owner scope and exits.
+    pub fn with_message_for_user(user_id: impl Into<String>, message: String) -> Self {
        Self {
+            user_id: user_id.into(),
            single_message: Some(message),
            debug_mode: Arc::new(AtomicBool::new(false)),
            is_streaming: Arc::new(AtomicBool::new(false)),
@@ -292,6 +306,7 @@ impl Channel for ReplChannel {
    async fn start(&self) -> Result<MessageStream, ChannelError> {
        let (tx, rx) = mpsc::channel(32);
        let single_message = self.single_message.clone();
+        let user_id = self.user_id.clone();
        let debug_mode = Arc::clone(&self.debug_mode);
        let suppress_banner = Arc::clone(&self.suppress_banner);
        let esc_interrupt_triggered_for_thread = Arc::new(AtomicBool::new(false));
@@ -301,11 +316,11 @@ impl Channel for ReplChannel {

            // Single message mode: send it and return
            if let Some(msg) = single_message {
-                let incoming = IncomingMessage::new("repl", "default", &msg).with_timezone(&sys_tz);
+                let incoming = IncomingMessage::new("repl", &user_id, &msg).with_timezone(&sys_tz);
                let _ = tx.blocking_send(incoming);
                // Ensure the agent exits after handling exactly one turn in -m mode,
                // even when other channels (gateway/http) are enabled.
-                let _ = tx.blocking_send(IncomingMessage::new("repl", "default", "/quit"));
+                let _ = tx.blocking_send(IncomingMessage::new("repl", &user_id, "/quit"));
                return;
            }

@@ -366,7 +381,7 @@ impl Channel for ReplChannel {
                            "/quit" | "/exit" => {
                                // Forward shutdown command so the agent loop exits even
                                // when other channels (e.g. web gateway) are still active.
-                                let msg = IncomingMessage::new("repl", "default", "/quit")
+                                let msg = IncomingMessage::new("repl", &user_id, "/quit")
                                    .with_timezone(&sys_tz);
                                let _ = tx.blocking_send(msg);
                                break;
@@ -389,7 +404,7 @@ impl Channel for ReplChannel {
                        }

                        let msg =
-                            IncomingMessage::new("repl", "default", line).with_timezone(&sys_tz);
+                            IncomingMessage::new("repl", &user_id, line).with_timezone(&sys_tz);
                        if tx.blocking_send(msg).is_err() {
                            break;
                        }
@@ -397,14 +412,14 @@ impl Channel for ReplChannel {
                    Err(ReadlineError::Interrupted) => {
                        if esc_interrupt_triggered_for_thread.swap(false, Ordering::Relaxed) {
                            // Esc: interrupt current operation and keep REPL open.
-                            let msg = IncomingMessage::new("repl", "default", "/interrupt")
+                            let msg = IncomingMessage::new("repl", &user_id, "/interrupt")
                                .with_timezone(&sys_tz);
                            if tx.blocking_send(msg).is_err() {
                                break;
                            }
                        } else {
                            // Ctrl+C (VINTR): request graceful shutdown.
-                            let msg = IncomingMessage::new("repl", "default", "/quit")
+                            let msg = IncomingMessage::new("repl", &user_id, "/quit")
                                .with_timezone(&sys_tz);
                            let _ = tx.blocking_send(msg);
                            break;
@@ -416,7 +431,7 @@ impl Channel for ReplChannel {
                        // immediately — just drop the REPL thread silently so other
                        // channels (gateway, telegram, …) keep running.
                        if std::io::stdin().is_terminal() {
-                            let msg = IncomingMessage::new("repl", "default", "/quit")
+                            let msg = IncomingMessage::new("repl", &user_id, "/quit")
                                .with_timezone(&sys_tz);
                            let _ = tx.blocking_send(msg);
                        }
@@ -524,6 +539,7 @@ impl Channel for ReplChannel {
                tool_name,
                description,
                parameters,
+                allow_always,
            } => {
                let term_width = crossterm::terminal::size()
                    .map(|(w, _)| w as usize)
@@ -567,9 +583,13 @@ impl Channel for ReplChannel {
                }

                eprintln!("  \u{2502}");
-                eprintln!(
-                    "  \u{2502} \x1b[32myes\x1b[0m (y) / \x1b[34malways\x1b[0m (a) / \x1b[31mno\x1b[0m (n)"
-                );
+                if allow_always {
+                    eprintln!(
+                        "  \u{2502} \x1b[32myes\x1b[0m (y) / \x1b[34malways\x1b[0m (a) / \x1b[31mno\x1b[0m (n)"
+                    );
+                } else {
+                    eprintln!("  \u{2502} \x1b[32myes\x1b[0m (y) / \x1b[31mno\x1b[0m (n)");
+                }
                eprintln!("  {bot_border}");
                eprintln!();
            }
@@ -915,20 +915,28 @@ impl Channel for SignalChannel {
            tool_name,
            description: _,
            parameters,
+            allow_always,
        } = &status
            && let Some(target_str) = metadata.get("signal_target").and_then(|v| v.as_str())
        {
            let params_json = serde_json::to_string_pretty(parameters).unwrap_or_default();
+            let always_line = if *allow_always {
+                format!(
+                    "\n• `always` or `a` - Approve and auto-approve future {} requests",
+                    tool_name
+                )
+            } else {
+                String::new()
+            };
            let message = format!(
                "⚠️ *Approval Required*\n\n\
                 *Request ID:* `{}`\n\
                 *Tool:* {}\n\
                 *Parameters:*\n```\n{}\n```\n\n\
                 Reply with:\n\
-                 • `yes` or `y` - Approve this request\n\
-                 • `always` or `a` - Approve and auto-approve future {} requests\n\
+                 • `yes` or `y` - Approve this request{}\n\
                 • `no` or `n` - Deny",
-                request_id, tool_name, params_json, tool_name
+                request_id, tool_name, params_json, always_line
            );
            self.send_status_message(target_str, &message).await;
        }
@@ -27,6 +27,7 @@ pub struct WasmChannelLoader {
    pairing_store: Arc<PairingStore>,
    settings_store: Option<Arc<dyn SettingsStore>>,
    secrets_store: Option<Arc<dyn SecretsStore + Send + Sync>>,
+    owner_scope_id: String,
 }

 impl WasmChannelLoader {
@@ -35,12 +36,14 @@ impl WasmChannelLoader {
        runtime: Arc<WasmChannelRuntime>,
        pairing_store: Arc<PairingStore>,
        settings_store: Option<Arc<dyn SettingsStore>>,
+        owner_scope_id: impl Into<String>,
    ) -> Self {
        Self {
            runtime,
            pairing_store,
            settings_store,
            secrets_store: None,
+            owner_scope_id: owner_scope_id.into(),
        }
    }

@@ -149,6 +152,7 @@ impl WasmChannelLoader {
            self.runtime.clone(),
            prepared,
            capabilities,
+            self.owner_scope_id.clone(),
            config_json,
            self.pairing_store.clone(),
            self.settings_store.clone(),
@@ -487,7 +491,8 @@ mod tests {
    async fn test_loader_invalid_name() {
        let config = WasmChannelRuntimeConfig::for_testing();
        let runtime = Arc::new(WasmChannelRuntime::new(config).unwrap());
-        let loader = WasmChannelLoader::new(runtime, Arc::new(PairingStore::new()), None);
+        let loader =
+            WasmChannelLoader::new(runtime, Arc::new(PairingStore::new()), None, "default");

        let dir = TempDir::new().unwrap();
        let wasm_path = dir.path().join("test.wasm");
@@ -505,7 +510,8 @@ mod tests {
    async fn load_from_dir_returns_empty_when_dir_missing() {
        let config = WasmChannelRuntimeConfig::for_testing();
        let runtime = Arc::new(WasmChannelRuntime::new(config).unwrap());
-        let loader = WasmChannelLoader::new(runtime, Arc::new(PairingStore::new()), None);
+        let loader =
+            WasmChannelLoader::new(runtime, Arc::new(PairingStore::new()), None, "default");

        let dir = TempDir::new().unwrap();
        let missing = dir.path().join("nonexistent_channels_dir");
@@ -69,7 +69,7 @@
 //! let runtime = WasmChannelRuntime::new(config)?;
 //!
 //! // Load channels from directory
-//! let loader = WasmChannelLoader::new(runtime);
+//! let loader = WasmChannelLoader::new(runtime, pairing_store, settings_store, owner_scope_id);
 //! let channels = loader.load_from_dir(Path::new("~/.ironclaw/channels/")).await?;
 //!
 //! // Add to channel manager
@@ -90,6 +90,7 @@ pub mod setup;
 pub(crate) mod signature;
 #[allow(dead_code)]
 pub(crate) mod storage;
+mod telegram_host_config;
 mod wrapper;

 // Core types
@@ -107,4 +108,5 @@ pub use schema::{
    ChannelCapabilitiesFile, ChannelConfig, SecretSetupSchema, SetupSchema, WebhookSchema,
 };
 pub use setup::{WasmChannelSetup, inject_channel_credentials, setup_wasm_channels};
+pub(crate) use telegram_host_config::{TELEGRAM_CHANNEL_NAME, bot_username_setting_key};
 pub use wrapper::{HttpResponse, SharedWasmChannel, WasmChannel};
@@ -672,6 +672,7 @@ mod tests {
            runtime,
            prepared,
            capabilities,
+            "default",
            "{}".to_string(),
            Arc::new(PairingStore::new()),
            None,
@@ -7,8 +7,9 @@ use std::collections::HashSet;
 use std::sync::Arc;

 use crate::channels::wasm::{
-    LoadedChannel, RegisteredEndpoint, SharedWasmChannel, WasmChannel, WasmChannelLoader,
-    WasmChannelRouter, WasmChannelRuntime, WasmChannelRuntimeConfig, create_wasm_channel_router,
+    LoadedChannel, RegisteredEndpoint, SharedWasmChannel, TELEGRAM_CHANNEL_NAME, WasmChannel,
+    WasmChannelLoader, WasmChannelRouter, WasmChannelRuntime, WasmChannelRuntimeConfig,
+    bot_username_setting_key, create_wasm_channel_router,
 };
 use crate::config::Config;
 use crate::db::Database;
@@ -48,7 +49,8 @@ pub async fn setup_wasm_channels(
    let mut loader = WasmChannelLoader::new(
        Arc::clone(&runtime),
        Arc::clone(&pairing_store),
-        settings_store,
+        settings_store.clone(),
+        config.owner_id.clone(),
    );
    if let Some(secrets) = secrets_store {
        loader = loader.with_secrets_store(Arc::clone(secrets));
@@ -70,7 +72,14 @@ pub async fn setup_wasm_channels(
    let mut channel_names: Vec<String> = Vec::new();

    for loaded in results.loaded {
-        let (name, channel) = register_channel(loaded, config, secrets_store, &wasm_router).await;
+        let (name, channel) = register_channel(
+            loaded,
+            config,
+            secrets_store,
+            settings_store.as_ref(),
+            &wasm_router,
+        )
+        .await;
        channel_names.push(name.clone());
        channels.push((name, channel));
    }
@@ -104,10 +113,16 @@ async fn register_channel(
    loaded: LoadedChannel,
    config: &Config,
    secrets_store: &Option<Arc<dyn SecretsStore + Send + Sync>>,
+    settings_store: Option<&Arc<dyn crate::db::SettingsStore>>,
    wasm_router: &Arc<WasmChannelRouter>,
 ) -> (String, Box<dyn crate::channels::Channel>) {
    let channel_name = loaded.name().to_string();
    tracing::info!("Loaded WASM channel: {}", channel_name);
+    let owner_actor_id = config
+        .channels
+        .wasm_channel_owner_ids
+        .get(channel_name.as_str())
+        .map(ToString::to_string);

    let secret_name = loaded.webhook_secret_name();
    let sig_key_secret_name = loaded.signature_key_secret_name();
@@ -115,7 +130,7 @@ async fn register_channel(

    let webhook_secret = if let Some(secrets) = secrets_store {
        secrets
-            .get_decrypted("default", &secret_name)
+            .get_decrypted(&config.owner_id, &secret_name)
            .await
            .ok()
            .map(|s| s.expose().to_string())
@@ -133,7 +148,7 @@ async fn register_channel(
        require_secret: webhook_secret.is_some(),
    }];

-    let channel_arc = Arc::new(loaded.channel);
+    let channel_arc = Arc::new(loaded.channel.with_owner_actor_id(owner_actor_id.clone()));

    // Inject runtime config (tunnel URL, webhook secret, owner_id).
    {
@@ -161,6 +176,15 @@ async fn register_channel(
            config_updates.insert("owner_id".to_string(), serde_json::json!(owner_id));
        }

+        if channel_name == TELEGRAM_CHANNEL_NAME
+            && let Some(store) = settings_store
+            && let Ok(Some(serde_json::Value::String(username))) = store
+                .get_setting("default", &bot_username_setting_key(&channel_name))
+                .await
+            && !username.trim().is_empty()
+        {
+            config_updates.insert("bot_username".to_string(), serde_json::json!(username));
+        }
        // Inject channel-specific secrets into config for channels that need
        // credentials in API request bodies (e.g., Feishu token exchange).
        // The credential injection system only replaces placeholders in URLs
@@ -198,7 +222,7 @@ async fn register_channel(
    // Register Ed25519 signature key if declared in capabilities.
    if let Some(ref sig_key_name) = sig_key_secret_name
        && let Some(secrets) = secrets_store
-        && let Ok(key_secret) = secrets.get_decrypted("default", sig_key_name).await
+        && let Ok(key_secret) = secrets.get_decrypted(&config.owner_id, sig_key_name).await
    {
        match wasm_router
            .register_signature_key(&channel_name, key_secret.expose())
@@ -216,7 +240,9 @@ async fn register_channel(
    // Register HMAC signing secret if declared in capabilities.
    if let Some(ref hmac_secret_name) = hmac_secret_name
        && let Some(secrets) = secrets_store
-        && let Ok(secret) = secrets.get_decrypted("default", hmac_secret_name).await
+        && let Ok(secret) = secrets
+            .get_decrypted(&config.owner_id, hmac_secret_name)
+            .await
    {
        wasm_router
            .register_hmac_secret(&channel_name, secret.expose())
@@ -231,6 +257,7 @@ async fn register_channel(
            .as_ref()
            .map(|s| s.as_ref() as &dyn SecretsStore),
        &channel_name,
+        &config.owner_id,
    )
    .await
    {
@@ -268,6 +295,7 @@ pub async fn inject_channel_credentials(
    channel: &Arc<WasmChannel>,
    secrets: Option<&dyn SecretsStore>,
    channel_name: &str,
+    owner_id: &str,
 ) -> anyhow::Result<usize> {
    if channel_name.trim().is_empty() {
        return Ok(0);
@@ -279,7 +307,7 @@ pub async fn inject_channel_credentials(
    // 1. Try injecting from persistent secrets store if available
    if let Some(secrets) = secrets {
        let all_secrets = secrets
-            .list("default")
+            .list(owner_id)
            .await
            .map_err(|e| anyhow::anyhow!("Failed to list secrets: {}", e))?;

@@ -290,7 +318,7 @@ pub async fn inject_channel_credentials(
                continue;
            }

-            let decrypted = match secrets.get_decrypted("default", &secret_meta.name).await {
+            let decrypted = match secrets.get_decrypted(owner_id, &secret_meta.name).await {
                Ok(d) => d,
                Err(e) => {
                    tracing::warn!(
@@ -0,0 +1,6 @@
+pub const TELEGRAM_CHANNEL_NAME: &str = "telegram";
+const TELEGRAM_BOT_USERNAME_SETTING_PREFIX: &str = "channels.wasm_channel_bot_usernames";
+
+pub fn bot_username_setting_key(channel_name: &str) -> String {
+    format!("{TELEGRAM_BOT_USERNAME_SETTING_PREFIX}.{channel_name}")
+}
@@ -162,15 +162,30 @@ pub async fn chat_auth_token_handler(
        .await
    {
        Ok(result) => {
-            clear_auth_mode(&state).await;
+            let mut resp = ActionResponse::ok(result.message.clone());
+            resp.activated = Some(result.activated);
+            resp.auth_url = result.auth_url.clone();
+            resp.verification = result.verification.clone();
+            resp.instructions = result.verification.as_ref().map(|v| v.instructions.clone());

-            state.sse.broadcast(SseEvent::AuthCompleted {
-                extension_name: req.extension_name.clone(),
-                success: true,
-                message: result.message.clone(),
-            });
+            if result.verification.is_some() {
+                state.sse.broadcast(SseEvent::AuthRequired {
+                    extension_name: req.extension_name.clone(),
+                    instructions: Some(result.message),
+                    auth_url: None,
+                    setup_url: None,
+                });
+            } else {
+                clear_auth_mode(&state).await;

-            Ok(Json(ActionResponse::ok(result.message)))
+                state.sse.broadcast(SseEvent::AuthCompleted {
+                    extension_name: req.extension_name.clone(),
+                    success: true,
+                    message: result.message,
+                });
+            }
+
+            Ok(Json(resp))
        }
        Err(e) => {
            let msg = e.to_string();
@@ -344,7 +359,7 @@ pub async fn chat_history_handler(
                    turn_number: t.turn_number,
                    user_input: t.user_input.clone(),
                    response: t.response.clone(),
-                    state: format!("{:?}", t.state()),
+                    state: format!("{:?}", t.state),
                    started_at: t.started_at.to_rfc3339(),
                    completed_at: t.completed_at.map(|dt| dt.to_rfc3339()),
                    tool_calls: t
@@ -497,7 +512,7 @@ pub async fn chat_threads_handler(
        .into_iter()
        .map(|t| ThreadInfo {
            id: t.id,
-            state: format!("{:?}", t.state()),
+            state: format!("{:?}", t.state),
            turn_count: t.turns.len(),
            created_at: t.created_at.to_rfc3339(),
            updated_at: t.updated_at.to_rfc3339(),
@@ -532,7 +547,7 @@ pub async fn chat_new_thread_handler(
        let id = thread.id;
        let info = ThreadInfo {
            id: thread.id,
-            state: format!("{:?}", thread.state()),
+            state: format!("{:?}", thread.state),
            turn_count: thread.turns.len(),
            created_at: thread.created_at.to_rfc3339(),
            updated_at: thread.updated_at.to_rfc3339(),
@@ -25,34 +25,34 @@ pub async fn extensions_list_handler(
        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;

    let pairing_store = crate::pairing::PairingStore::new();
+    let mut owner_bound_channels = std::collections::HashSet::new();
+    for ext in &installed {
+        if ext.kind == crate::extensions::ExtensionKind::WasmChannel
+            && ext_mgr.has_wasm_channel_owner_binding(&ext.name).await
+        {
+            owner_bound_channels.insert(ext.name.clone());
+        }
+    }
    let extensions = installed
        .into_iter()
        .map(|ext| {
            let activation_status = if ext.kind == crate::extensions::ExtensionKind::WasmChannel {
-                Some(if ext.activation_error.is_some() {
-                    "failed".to_string()
-                } else if !ext.authenticated {
-                    "installed".to_string()
-                } else if ext.active {
-                    let has_paired = pairing_store
-                        .read_allow_from(&ext.name)
-                        .map(|list| !list.is_empty())
-                        .unwrap_or(false);
-                    if has_paired {
-                        "active".to_string()
-                    } else {
-                        "pairing".to_string()
-                    }
-                } else {
-                    "configured".to_string()
-                })
+                let has_paired = pairing_store
+                    .read_allow_from(&ext.name)
+                    .map(|list| !list.is_empty())
+                    .unwrap_or(false);
+                crate::channels::web::types::classify_wasm_channel_activation(
+                    &ext,
+                    has_paired,
+                    owner_bound_channels.contains(&ext.name),
+                )
            } else if ext.kind == crate::extensions::ExtensionKind::ChannelRelay {
                Some(if ext.active {
-                    "active".to_string()
+                    crate::channels::web::types::ExtensionActivationStatus::Active
                } else if ext.authenticated {
-                    "configured".to_string()
+                    crate::channels::web::types::ExtensionActivationStatus::Configured
                } else {
-                    "installed".to_string()
+                    crate::channels::web::types::ExtensionActivationStatus::Installed
                })
            } else {
                None
@@ -102,6 +102,7 @@ impl GatewayChannel {
            cost_guard: None,
            routine_engine: Arc::new(tokio::sync::RwLock::new(None)),
            startup_time: std::time::Instant::now(),
+            active_config: server::ActiveConfigSnapshot::default(),
        });

        Self {
@@ -139,6 +140,7 @@ impl GatewayChannel {
            cost_guard: self.state.cost_guard.clone(),
            routine_engine: Arc::clone(&self.state.routine_engine),
            startup_time: self.state.startup_time,
+            active_config: self.state.active_config.clone(),
        };
        mutate(&mut new_state);
        self.state = Arc::new(new_state);
@@ -250,6 +252,12 @@ impl GatewayChannel {
        self
    }

+    /// Inject the active (resolved) configuration snapshot for the status endpoint.
+    pub fn with_active_config(mut self, config: server::ActiveConfigSnapshot) -> Self {
+        self.rebuild_state(|s| s.active_config = config);
+        self
+    }
+
    /// Get the auth token (for printing to console on startup).
    pub fn auth_token(&self) -> &str {
        &self.auth_token
@@ -366,6 +374,7 @@ impl Channel for GatewayChannel {
                tool_name,
                description,
                parameters,
+                allow_always,
            } => SseEvent::ApprovalNeeded {
                request_id,
                tool_name,
@@ -373,6 +382,7 @@ impl Channel for GatewayChannel {
                parameters: serde_json::to_string_pretty(&parameters)
                    .unwrap_or_else(|_| parameters.to_string()),
                thread_id,
+                allow_always,
            },
            StatusUpdate::AuthRequired {
                extension_name,
@@ -19,6 +19,7 @@ use axum::{
    routing::{get, post},
 };
 use serde::Deserialize;
+use sha2::{Digest, Sha256};
 use tokio::sync::{mpsc, oneshot};
 use tokio_stream::StreamExt;
 use tower_http::cors::{AllowHeaders, CorsLayer};
@@ -26,7 +27,6 @@ use tower_http::set_header::SetResponseHeaderLayer;
 use uuid::Uuid;

 use crate::agent::SessionManager;
-use crate::agent::routine::{Trigger, next_cron_fire};
 use crate::bootstrap::ironclaw_base_dir;
 use crate::channels::IncomingMessage;
 use crate::channels::relay::DEFAULT_RELAY_NAME;
@@ -36,6 +36,7 @@ use crate::channels::web::handlers::jobs::{
    jobs_events_handler, jobs_list_handler, jobs_prompt_handler, jobs_restart_handler,
    jobs_summary_handler,
 };
+use crate::channels::web::handlers::routines::{routines_delete_handler, routines_toggle_handler};
 use crate::channels::web::handlers::skills::{
    skills_install_handler, skills_list_handler, skills_remove_handler, skills_search_handler,
 };
@@ -63,6 +64,16 @@ pub type PromptQueue = Arc<
 pub type RoutineEngineSlot =
    Arc<tokio::sync::RwLock<Option<Arc<crate::agent::routine_engine::RoutineEngine>>>>;

+fn redact_oauth_state_for_logs(state: &str) -> String {
+    let digest = Sha256::digest(state.as_bytes());
+    let mut short_hash = String::with_capacity(12);
+    for byte in &digest[..6] {
+        use std::fmt::Write as _;
+        let _ = write!(&mut short_hash, "{byte:02x}");
+    }
+    format!("sha256:{short_hash}:len={}", state.len())
+}
+
 /// Simple sliding-window rate limiter.
 ///
 /// Tracks the number of requests in the current window. Resets when the window expires.
@@ -126,6 +137,14 @@ impl RateLimiter {
    }
 }

+/// Snapshot of the active (resolved) configuration exposed to the frontend.
+#[derive(Debug, Clone, Default, serde::Serialize)]
+pub struct ActiveConfigSnapshot {
+    pub llm_backend: String,
+    pub llm_model: String,
+    pub enabled_channels: Vec<String>,
+}
+
 /// Shared state for all gateway handlers.
 pub struct GatewayState {
    /// Channel to send messages to the agent loop.
@@ -177,6 +196,8 @@ pub struct GatewayState {
    pub routine_engine: RoutineEngineSlot,
    /// Server startup time for uptime calculation.
    pub startup_time: std::time::Instant,
+    /// Snapshot of active (resolved) configuration for the frontend.
+    pub active_config: ActiveConfigSnapshot,
 }

 /// Start the gateway HTTP server.
@@ -208,7 +229,8 @@ pub async fn start_server(
        .route(
            "/oauth/slack/callback",
            get(slack_relay_oauth_callback_handler),
-        );
+        )
+        .route("/relay/events", post(relay_events_handler));

    // Protected routes (require auth)
    let auth_state = AuthState { token: auth_token };
@@ -555,22 +577,35 @@ async fn oauth_callback_handler(
        }
    };

-    // Strip instance prefix from state for registry lookup.
-    // Platform nginx sends `state=instance:nonce` but flows are keyed by nonce only.
-    let lookup_key = oauth_defaults::strip_instance_prefix(&state_param);
+    let decoded_state = match oauth_defaults::decode_hosted_oauth_state(&state_param) {
+        Ok(decoded) => decoded,
+        Err(error) => {
+            let redacted_state = redact_oauth_state_for_logs(&state_param);
+            tracing::warn!(
+                state = %redacted_state,
+                error = %error,
+                "OAuth callback received with malformed state"
+            );
+            clear_auth_mode(&state).await;
+            return oauth_error_page("IronClaw");
+        }
+    };
+    let lookup_key = decoded_state.flow_id.clone();

    let flow = ext_mgr
        .pending_oauth_flows()
        .write()
        .await
-        .remove(lookup_key);
+        .remove(&lookup_key);

    let flow = match flow {
        Some(f) => f,
        None => {
+            let redacted_state = redact_oauth_state_for_logs(&state_param);
+            let redacted_lookup_key = redact_oauth_state_for_logs(&lookup_key);
            tracing::warn!(
-                state = %state_param,
-                lookup_key = %lookup_key,
+                state = %redacted_state,
+                lookup_key = %redacted_lookup_key,
                "OAuth callback received with unknown or expired state"
            );
            clear_auth_mode(&state).await;
@@ -597,33 +632,29 @@ async fn oauth_callback_handler(
    }

    // Exchange the authorization code for tokens.
-    // Use the platform exchange proxy when configured (keeps client_secret off container),
-    // otherwise call the provider's token URL directly.
-    let exchange_proxy_url = std::env::var("IRONCLAW_OAUTH_EXCHANGE_URL").ok();
+    // Use the platform exchange proxy when configured, otherwise call the
+    // provider's token URL directly.
+    let exchange_proxy_url = oauth_defaults::exchange_proxy_url();

    let result: Result<(), String> = async {
-        let token_response = if let (Some(proxy_url), None) = (&exchange_proxy_url, &flow.resource)
-        {
-            // Use the platform exchange proxy when configured and no resource
-            // parameter is needed. The proxy holds client_secret server-side so
-            // the container never sees it. MCP flows (resource.is_some()) bypass
-            // the proxy because it doesn't forward the RFC 8707 resource param.
+        let token_response = if let Some(proxy_url) = &exchange_proxy_url {
            let gateway_token = flow.gateway_token.as_deref().unwrap_or_default();
-            oauth_defaults::exchange_via_proxy(
+            oauth_defaults::exchange_via_proxy(oauth_defaults::ProxyTokenExchangeRequest {
                proxy_url,
                gateway_token,
-                &code,
-                &flow.redirect_uri,
-                flow.code_verifier.as_deref(),
-                &flow.access_token_field,
-            )
+                token_url: &flow.token_url,
+                client_id: &flow.client_id,
+                client_secret: flow.client_secret.as_deref(),
+                code: &code,
+                redirect_uri: &flow.redirect_uri,
+                code_verifier: flow.code_verifier.as_deref(),
+                access_token_field: &flow.access_token_field,
+                extra_token_params: &flow.token_exchange_extra_params,
+            })
            .await
            .map_err(|e| e.to_string())?
        } else {
-            // Direct token exchange: uses exchange_oauth_code_with_resource so MCP
-            // flows can include the RFC 8707 `resource` parameter to scope the
-            // issued token to the specific MCP server.
-            oauth_defaults::exchange_oauth_code_with_resource(
+            oauth_defaults::exchange_oauth_code_with_params(
                &flow.token_url,
                &flow.client_id,
                flow.client_secret.as_deref(),
@@ -631,7 +662,7 @@ async fn oauth_callback_handler(
                &flow.redirect_uri,
                flow.code_verifier.as_deref(),
                &flow.access_token_field,
-                flow.resource.as_deref(),
+                &flow.token_exchange_extra_params,
            )
            .await
            .map_err(|e| e.to_string())?
@@ -658,10 +689,8 @@ async fn oauth_callback_handler(
        .await
        .map_err(|e| e.to_string())?;

-        // For MCP OAuth flows (identified by resource field), persist the
-        // client_id so token refresh works without re-authentication.
-        // The CLI flow stores this in authorize_mcp_server(); the gateway
-        // callback must do the same.
+        // Persist the client_id for flows that need it after the session ends
+        // (for example DCR-based MCP refresh).
        if let Some(ref client_id_secret) = flow.client_id_secret_name {
            let params = crate::secrets::CreateSecretParams::new(client_id_secret, &flow.client_id)
                .with_provider(flow.provider.as_ref().cloned().unwrap_or_default());
@@ -742,11 +771,103 @@ async fn oauth_callback_handler(
    axum::response::Html(html).into_response()
 }

+/// Webhook endpoint for receiving relay events from channel-relay.
+///
+/// PUBLIC route — authenticated via HMAC signature (X-Relay-Signature header).
+async fn relay_events_handler(
+    State(state): State<Arc<GatewayState>>,
+    headers: axum::http::HeaderMap,
+    body: axum::body::Bytes,
+) -> impl IntoResponse {
+    let ext_mgr = match state.extension_manager.as_ref() {
+        Some(mgr) => mgr,
+        None => {
+            return (StatusCode::SERVICE_UNAVAILABLE, "not ready").into_response();
+        }
+    };
+
+    let signing_secret = match ext_mgr.relay_signing_secret() {
+        Some(s) => s,
+        None => {
+            return (StatusCode::SERVICE_UNAVAILABLE, "relay not configured").into_response();
+        }
+    };
+
+    // Verify signature
+    let signature = match headers
+        .get("x-relay-signature")
+        .and_then(|v| v.to_str().ok())
+    {
+        Some(s) => s.to_string(),
+        None => {
+            return (StatusCode::UNAUTHORIZED, "missing signature").into_response();
+        }
+    };
+
+    let timestamp = match headers
+        .get("x-relay-timestamp")
+        .and_then(|v| v.to_str().ok())
+    {
+        Some(t) => t.to_string(),
+        None => {
+            return (StatusCode::UNAUTHORIZED, "missing timestamp").into_response();
+        }
+    };
+
+    // Check timestamp freshness (5 min window)
+    let ts: i64 = match timestamp.parse() {
+        Ok(t) => t,
+        Err(_) => {
+            return (StatusCode::BAD_REQUEST, "malformed timestamp").into_response();
+        }
+    };
+    let now = chrono::Utc::now().timestamp();
+    if (now - ts).abs() > 300 {
+        return (StatusCode::UNAUTHORIZED, "stale timestamp").into_response();
+    }
+
+    // Verify HMAC: sha256(secret, timestamp + "." + body)
+    if !crate::channels::relay::webhook::verify_relay_signature(
+        &signing_secret,
+        &timestamp,
+        &body,
+        &signature,
+    ) {
+        return (StatusCode::UNAUTHORIZED, "invalid signature").into_response();
+    }
+
+    // Parse event
+    let event: crate::channels::relay::client::ChannelEvent = match serde_json::from_slice(&body) {
+        Ok(e) => e,
+        Err(e) => {
+            tracing::warn!(error = %e, "relay callback invalid JSON");
+            return (StatusCode::BAD_REQUEST, "invalid JSON").into_response();
+        }
+    };
+
+    // Push to relay channel
+    let event_tx_guard = ext_mgr.relay_event_tx();
+    let event_tx = event_tx_guard.lock().await;
+    match event_tx.as_ref() {
+        Some(tx) => {
+            if let Err(e) = tx.try_send(event) {
+                tracing::warn!(error = %e, "relay event channel full or closed");
+                return (StatusCode::SERVICE_UNAVAILABLE, "event queue full").into_response();
+            }
+        }
+        None => {
+            return (StatusCode::SERVICE_UNAVAILABLE, "relay channel not active").into_response();
+        }
+    }
+
+    Json(serde_json::json!({"ok": true})).into_response()
+}
+
 /// OAuth callback for Slack via channel-relay.
 ///
 /// This is a PUBLIC route (no Bearer token required) because channel-relay
 /// redirects the user's browser here after Slack OAuth completes.
-/// Query params: `stream_token`, `provider`, `team_id`.
+/// Query params: `provider`, `team_id`.
 async fn slack_relay_oauth_callback_handler(
    State(state): State<Arc<GatewayState>>,
    Query(params): Query<std::collections::HashMap<String, String>>,
@@ -763,27 +884,6 @@ async fn slack_relay_oauth_callback_handler(
        .into_response();
    }

-    // Validate stream_token: required, non-empty, max 2048 bytes
-    let stream_token = match params.get("stream_token") {
-        Some(t) if !t.is_empty() && t.len() <= 2048 => t.clone(),
-        Some(t) if t.len() > 2048 => {
-            return axum::response::Html(
-                "<html><body style='font-family: system-ui; text-align: center; padding: 60px;'>\
-                 <h2>Error</h2><p>Invalid callback parameters.</p></body></html>"
-                    .to_string(),
-            )
-            .into_response();
-        }
-        _ => {
-            return axum::response::Html(
-                "<html><body style='font-family: system-ui; text-align: center; padding: 60px;'>\
-                 <h2>Error</h2><p>Invalid callback parameters.</p></body></html>"
-                    .to_string(),
-            )
-            .into_response();
-        }
-    };
-
    // Validate team_id format: empty or T followed by alphanumeric (max 20 chars)
    let team_id = params.get("team_id").cloned().unwrap_or_default();
    if !team_id.is_empty() {
@@ -869,30 +969,16 @@ async fn slack_relay_oauth_callback_handler(
    let _ = ext_mgr.secrets().delete(&state.user_id, &state_key).await;

    let result: Result<(), String> = async {
-        // Store the stream token as a secret
-        let token_key = format!("relay:{}:stream_token", DEFAULT_RELAY_NAME);
-        let _ = ext_mgr.secrets().delete(&state.user_id, &token_key).await;
-        ext_mgr
-            .secrets()
-            .create(
-                &state.user_id,
-                crate::secrets::CreateSecretParams {
-                    name: token_key,
-                    value: secrecy::SecretString::from(stream_token),
-                    provider: Some(provider.clone()),
-                    expires_at: None,
-                },
-            )
-            .await
-            .map_err(|e| format!("Failed to store stream token: {}", e))?;
+        let store = state.store.as_ref().ok_or_else(|| {
+            "Relay activation requires persistent settings storage; no-db mode is unsupported."
+                .to_string()
+        })?;

        // Store team_id in settings
-        if let Some(ref store) = state.store {
-            let team_id_key = format!("relay:{}:team_id", DEFAULT_RELAY_NAME);
-            let _ = store
-                .set_setting(&state.user_id, &team_id_key, &serde_json::json!(team_id))
-                .await;
-        }
+        let team_id_key = format!("relay:{}:team_id", DEFAULT_RELAY_NAME);
+        let _ = store
+            .set_setting(&state.user_id, &team_id_key, &serde_json::json!(team_id))
+            .await;

        // Activate the relay channel
        ext_mgr
@@ -1163,19 +1249,43 @@ async fn chat_auth_token_handler(
        .configure_token(&req.extension_name, &req.token)
        .await
    {
-        Ok(result) if result.activated => {
-            // Clear auth mode on the active thread
-            clear_auth_mode(&state).await;
+        Ok(result) => {
+            let mut resp = if result.verification.is_some() || result.activated {
+                ActionResponse::ok(result.message.clone())
+            } else {
+                ActionResponse::fail(result.message.clone())
+            };
+            resp.activated = Some(result.activated);
+            resp.auth_url = result.auth_url.clone();
+            resp.verification = result.verification.clone();
+            resp.instructions = result.verification.as_ref().map(|v| v.instructions.clone());

-            state.sse.broadcast(SseEvent::AuthCompleted {
-                extension_name: req.extension_name.clone(),
-                success: true,
-                message: result.message.clone(),
-            });
+            if result.verification.is_some() {
+                state.sse.broadcast(SseEvent::AuthRequired {
+                    extension_name: req.extension_name.clone(),
+                    instructions: Some(result.message),
+                    auth_url: None,
+                    setup_url: None,
+                });
+            } else if result.activated {
+                // Clear auth mode on the active thread
+                clear_auth_mode(&state).await;

-            Ok(Json(ActionResponse::ok(result.message)))
+                state.sse.broadcast(SseEvent::AuthCompleted {
+                    extension_name: req.extension_name.clone(),
+                    success: true,
+                    message: result.message,
+                });
+            } else {
+                state.sse.broadcast(SseEvent::AuthCompleted {
+                    extension_name: req.extension_name.clone(),
+                    success: false,
+                    message: result.message,
+                });
+            }
+
+            Ok(Json(resp))
        }
-        Ok(result) => Ok(Json(ActionResponse::fail(result.message))),
        Err(e) => {
            let msg = e.to_string();
            // Re-emit auth_required for retry on validation errors
@@ -1354,7 +1464,7 @@ async fn chat_history_handler(
                turn_number: t.turn_number,
                user_input: t.user_input.clone(),
                response: t.response.clone(),
-                state: format!("{:?}", t.state()),
+                state: format!("{:?}", t.state),
                started_at: t.started_at.to_rfc3339(),
                completed_at: t.completed_at.map(|dt| dt.to_rfc3339()),
                tool_calls: t
@@ -1500,7 +1610,7 @@ async fn chat_threads_handler(
        .into_iter()
        .map(|t| ThreadInfo {
            id: t.id,
-            state: format!("{:?}", t.state()),
+            state: format!("{:?}", t.state),
            turn_count: t.turns.len(),
            created_at: t.created_at.to_rfc3339(),
            updated_at: t.updated_at.to_rfc3339(),
@@ -1532,7 +1642,7 @@ async fn chat_new_thread_handler(
        let id = thread.id;
        let info = ThreadInfo {
            id: thread.id,
-            state: format!("{:?}", thread.state()),
+            state: format!("{:?}", thread.state),
            turn_count: thread.turns.len(),
            created_at: thread.created_at.to_rfc3339(),
            updated_at: thread.updated_at.to_rfc3339(),
@@ -1818,29 +1928,34 @@ async fn extensions_list_handler(
        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;

    let pairing_store = crate::pairing::PairingStore::new();
+    let mut owner_bound_channels = std::collections::HashSet::new();
+    for ext in &installed {
+        if ext.kind == crate::extensions::ExtensionKind::WasmChannel
+            && ext_mgr.has_wasm_channel_owner_binding(&ext.name).await
+        {
+            owner_bound_channels.insert(ext.name.clone());
+        }
+    }
    let extensions = installed
        .into_iter()
        .map(|ext| {
            let activation_status = if ext.kind == crate::extensions::ExtensionKind::WasmChannel {
-                Some(if ext.activation_error.is_some() {
-                    "failed".to_string()
-                } else if !ext.authenticated {
-                    // No credentials configured yet.
-                    "installed".to_string()
-                } else if ext.active {
-                    // Check pairing status for active channels.
-                    let has_paired = pairing_store
-                        .read_allow_from(&ext.name)
-                        .map(|list| !list.is_empty())
-                        .unwrap_or(false);
-                    if has_paired {
-                        "active".to_string()
-                    } else {
-                        "pairing".to_string()
-                    }
+                let has_paired = pairing_store
+                    .read_allow_from(&ext.name)
+                    .map(|list| !list.is_empty())
+                    .unwrap_or(false);
+                crate::channels::web::types::classify_wasm_channel_activation(
+                    &ext,
+                    has_paired,
+                    owner_bound_channels.contains(&ext.name),
+                )
+            } else if ext.kind == crate::extensions::ExtensionKind::ChannelRelay {
+                Some(if ext.active {
+                    ExtensionActivationStatus::Active
+                } else if ext.authenticated {
+                    ExtensionActivationStatus::Configured
                } else {
-                    // Authenticated but not yet active.
-                    "configured".to_string()
+                    ExtensionActivationStatus::Installed
                })
            } else {
                None
@@ -2205,20 +2320,24 @@ async fn extensions_setup_submit_handler(

    match ext_mgr.configure(&name, &req.secrets).await {
        Ok(result) => {
-            // Broadcast completion status so chat UI can dismiss success cases while
-            // leaving failed auth/configuration flows visible for correction.
-            state.sse.broadcast(SseEvent::AuthCompleted {
-                extension_name: name.clone(),
-                success: result.activated,
-                message: result.message.clone(),
-            });
-            let mut resp = if result.activated {
+            let mut resp = if result.verification.is_some() || result.activated {
                ActionResponse::ok(result.message)
            } else {
                ActionResponse::fail(result.message)
            };
            resp.activated = Some(result.activated);
-            resp.auth_url = result.auth_url;
+            resp.auth_url = result.auth_url.clone();
+            resp.verification = result.verification.clone();
+            resp.instructions = result.verification.as_ref().map(|v| v.instructions.clone());
+            if result.verification.is_none() {
+                // Broadcast auth_completed so the chat UI can dismiss any in-progress
+                // auth card or setup modal that was triggered by tool_auth/tool_activate.
+                state.sse.broadcast(SseEvent::AuthCompleted {
+                    extension_name: name.clone(),
+                    success: result.activated,
+                    message: resp.message.clone(),
+                });
+            }
            Ok(Json(resp))
        }
        Err(e) => Ok(Json(ActionResponse::fail(e.to_string()))),
@@ -2430,83 +2549,6 @@ async fn routines_trigger_handler(
    })))
 }

-#[derive(Deserialize)]
-struct ToggleRequest {
-    enabled: Option<bool>,
-}
-
-async fn routines_toggle_handler(
-    State(state): State<Arc<GatewayState>>,
-    Path(id): Path<String>,
-    body: Option<Json<ToggleRequest>>,
-) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
-    let store = state.store.as_ref().ok_or((
-        StatusCode::SERVICE_UNAVAILABLE,
-        "Database not available".to_string(),
-    ))?;
-
-    let routine_id = Uuid::parse_str(&id)
-        .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid routine ID".to_string()))?;
-
-    let mut routine = store
-        .get_routine(routine_id)
-        .await
-        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
-        .ok_or((StatusCode::NOT_FOUND, "Routine not found".to_string()))?;
-
-    let was_enabled = routine.enabled;
-    // If a specific value was provided, use it; otherwise toggle.
-    routine.enabled = match body {
-        Some(Json(req)) => req.enabled.unwrap_or(!routine.enabled),
-        None => !routine.enabled,
-    };
-
-    if routine.enabled
-        && !was_enabled
-        && let Trigger::Cron { schedule, timezone } = &routine.trigger
-    {
-        routine.next_fire_at = next_cron_fire(schedule, timezone.as_deref())
-            .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
-    }
-
-    store
-        .update_routine(&routine)
-        .await
-        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
-
-    Ok(Json(serde_json::json!({
-        "status": if routine.enabled { "enabled" } else { "disabled" },
-        "routine_id": routine_id,
-    })))
-}
-
-async fn routines_delete_handler(
-    State(state): State<Arc<GatewayState>>,
-    Path(id): Path<String>,
-) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
-    let store = state.store.as_ref().ok_or((
-        StatusCode::SERVICE_UNAVAILABLE,
-        "Database not available".to_string(),
-    ))?;
-
-    let routine_id = Uuid::parse_str(&id)
-        .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid routine ID".to_string()))?;
-
-    let deleted = store
-        .delete_routine(routine_id)
-        .await
-        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
-
-    if deleted {
-        Ok(Json(serde_json::json!({
-            "status": "deleted",
-            "routine_id": routine_id,
-        })))
-    } else {
-        Err((StatusCode::NOT_FOUND, "Routine not found".to_string()))
-    }
-}
-
 async fn routines_runs_handler(
    State(state): State<Arc<GatewayState>>,
    Path(id): Path<String>,
@@ -2713,6 +2755,9 @@ async fn gateway_status_handler(
        daily_cost,
        actions_this_hour,
        model_usage,
+        llm_backend: state.active_config.llm_backend.clone(),
+        llm_model: state.active_config.llm_model.clone(),
+        enabled_channels: state.active_config.enabled_channels.clone(),
    })
 }

@@ -2738,12 +2783,19 @@ struct GatewayStatusResponse {
    actions_this_hour: Option<u64>,
    #[serde(skip_serializing_if = "Option::is_none")]
    model_usage: Option<Vec<ModelUsageEntry>>,
+    llm_backend: String,
+    llm_model: String,
+    enabled_channels: Vec<String>,
 }

 #[cfg(test)]
 mod tests {
    use super::*;
+    use crate::channels::web::types::{
+        ExtensionActivationStatus, classify_wasm_channel_activation,
+    };
    use crate::cli::oauth_defaults;
+    use crate::extensions::{ExtensionKind, InstalledExtension};
    use crate::testing::credentials::TEST_GATEWAY_CRYPTO_KEY;

    #[test]
@@ -2822,6 +2874,85 @@ mod tests {
        assert!(turns.is_empty());
    }

+    #[test]
+    fn test_wasm_channel_activation_status_owner_bound_counts_as_active() -> Result<(), String> {
+        let ext = InstalledExtension {
+            name: "telegram".to_string(),
+            kind: ExtensionKind::WasmChannel,
+            display_name: Some("Telegram".to_string()),
+            description: None,
+            url: None,
+            authenticated: true,
+            active: true,
+            tools: Vec::new(),
+            needs_setup: true,
+            has_auth: false,
+            installed: true,
+            activation_error: None,
+            version: None,
+        };
+
+        let owner_bound = classify_wasm_channel_activation(&ext, false, true);
+        if owner_bound != Some(ExtensionActivationStatus::Active) {
+            return Err(format!(
+                "owner-bound channel should be active, got {:?}",
+                owner_bound
+            ));
+        }
+
+        let unbound = classify_wasm_channel_activation(&ext, false, false);
+        if unbound != Some(ExtensionActivationStatus::Pairing) {
+            return Err(format!(
+                "unbound channel should be pairing, got {:?}",
+                unbound
+            ));
+        }
+
+        Ok(())
+    }
+
+    #[test]
+    fn test_channel_relay_activation_status_is_preserved() -> Result<(), String> {
+        let relay = InstalledExtension {
+            name: "signal".to_string(),
+            kind: ExtensionKind::ChannelRelay,
+            display_name: Some("Signal".to_string()),
+            description: None,
+            url: None,
+            authenticated: true,
+            active: false,
+            tools: Vec::new(),
+            needs_setup: true,
+            has_auth: false,
+            installed: true,
+            activation_error: None,
+            version: None,
+        };
+
+        let status = if relay.kind == crate::extensions::ExtensionKind::WasmChannel {
+            classify_wasm_channel_activation(&relay, false, false)
+        } else if relay.kind == crate::extensions::ExtensionKind::ChannelRelay {
+            Some(if relay.active {
+                ExtensionActivationStatus::Active
+            } else if relay.authenticated {
+                ExtensionActivationStatus::Configured
+            } else {
+                ExtensionActivationStatus::Installed
+            })
+        } else {
+            None
+        };
+
+        if status != Some(ExtensionActivationStatus::Configured) {
+            return Err(format!(
+                "channel relay should retain configured status, got {:?}",
+                status
+            ));
+        }
+
+        Ok(())
+    }
+
    // --- OAuth callback handler tests ---

    /// Build a minimal `GatewayState` for testing the OAuth callback handler.
@@ -2851,6 +2982,7 @@ mod tests {
            cost_guard: None,
            routine_engine: Arc::new(tokio::sync::RwLock::new(None)),
            startup_time: std::time::Instant::now(),
+            active_config: ActiveConfigSnapshot::default(),
        })
    }

@@ -2935,6 +3067,92 @@ mod tests {
        );
    }

+    #[tokio::test]
+    async fn test_extensions_setup_submit_telegram_verification_does_not_broadcast_auth_required() {
+        use axum::body::Body;
+        use tokio::time::{Duration, timeout};
+        use tower::ServiceExt;
+
+        let secrets = test_secrets_store();
+        let (ext_mgr, _wasm_tools_dir, wasm_channels_dir) = test_ext_mgr(secrets);
+
+        std::fs::write(
+            wasm_channels_dir.path().join("telegram.wasm"),
+            b"\0asm fake",
+        )
+        .expect("write fake telegram wasm");
+        let caps = serde_json::json!({
+            "type": "channel",
+            "name": "telegram",
+            "setup": {
+                "required_secrets": [
+                    {
+                        "name": "telegram_bot_token",
+                        "prompt": "Enter your Telegram Bot API token (from @BotFather)"
+                    }
+                ]
+            }
+        });
+        std::fs::write(
+            wasm_channels_dir.path().join("telegram.capabilities.json"),
+            serde_json::to_string(&caps).expect("serialize telegram caps"),
+        )
+        .expect("write telegram caps");
+
+        ext_mgr
+            .set_test_telegram_pending_verification("iclaw-7qk2m9", Some("test_hot_bot"))
+            .await;
+
+        let state = test_gateway_state(Some(ext_mgr));
+        let mut receiver = state.sse.sender().subscribe();
+        let app = Router::new()
+            .route(
+                "/api/extensions/{name}/setup",
+                post(extensions_setup_submit_handler),
+            )
+            .with_state(state);
+
+        let req_body = serde_json::json!({
+            "secrets": {
+                "telegram_bot_token": "123456789:ABCdefGhI"
+            }
+        });
+        let req = axum::http::Request::builder()
+            .method("POST")
+            .uri("/api/extensions/telegram/setup")
+            .header("content-type", "application/json")
+            .body(Body::from(req_body.to_string()))
+            .expect("request");
+
+        let resp = ServiceExt::<axum::http::Request<Body>>::oneshot(app, req)
+            .await
+            .expect("response");
+        assert_eq!(resp.status(), StatusCode::OK);
+
+        let body = axum::body::to_bytes(resp.into_body(), 1024 * 64)
+            .await
+            .expect("body");
+        let parsed: serde_json::Value = serde_json::from_slice(&body).expect("json response");
+        assert_eq!(parsed["success"], serde_json::Value::Bool(true));
+        assert_eq!(parsed["activated"], serde_json::Value::Bool(false));
+        assert_eq!(parsed["verification"]["code"], "iclaw-7qk2m9");
+
+        let deadline = tokio::time::Instant::now() + Duration::from_millis(100);
+        loop {
+            let remaining = deadline.saturating_duration_since(tokio::time::Instant::now());
+            if remaining.is_zero() {
+                break;
+            }
+            match timeout(remaining, receiver.recv()).await {
+                Ok(Ok(crate::channels::web::types::SseEvent::AuthRequired { .. })) => {
+                    panic!("verification responses should not emit auth_required SSE events")
+                }
+                Ok(Ok(_)) => continue,
+                Ok(Err(_)) | Err(_) => break,
+            }
+        }
+    }
+
    fn expired_flow_created_at() -> Option<std::time::Instant> {
        std::time::Instant::now()
            .checked_sub(oauth_defaults::OAUTH_FLOW_EXPIRY + std::time::Duration::from_secs(1))
@@ -3111,7 +3329,7 @@ mod tests {
            secrets,
            sse_sender: None,
            gateway_token: None,
-            resource: None,
+            token_exchange_extra_params: std::collections::HashMap::new(),
            client_id_secret_name: None,
            created_at,
        };
@@ -3179,7 +3397,7 @@ mod tests {
            secrets,
            sse_sender: Some(sender),
            gateway_token: None,
-            resource: None,
+            token_exchange_extra_params: std::collections::HashMap::new(),
            client_id_secret_name: None,
            created_at,
        };
@@ -3282,7 +3500,7 @@ mod tests {
            secrets,
            sse_sender: None,
            gateway_token: None,
-            resource: None,
+            token_exchange_extra_params: std::collections::HashMap::new(),
            client_id_secret_name: None,
            // Expired — handler will reject after lookup (no network I/O)
            created_at,
@@ -3334,6 +3552,85 @@ mod tests {
        );
    }

+    #[tokio::test]
+    async fn test_oauth_callback_accepts_versioned_hosted_state() {
+        use axum::body::Body;
+        use tower::ServiceExt;
+
+        let secrets: Arc<dyn crate::secrets::SecretsStore + Send + Sync> =
+            Arc::new(crate::secrets::InMemorySecretsStore::new(Arc::new(
+                crate::secrets::SecretsCrypto::new(secrecy::SecretString::from(
+                    TEST_GATEWAY_CRYPTO_KEY.to_string(),
+                ))
+                .expect("crypto"),
+            )));
+        let (ext_mgr, _wasm_tools_dir, _wasm_channels_dir) = test_ext_mgr(secrets.clone());
+
+        let Some(created_at) = expired_flow_created_at() else {
+            eprintln!("Skipping versioned OAuth state test: monotonic uptime below expiry window");
+            return;
+        };
+        let flow = crate::cli::oauth_defaults::PendingOAuthFlow {
+            extension_name: "test_tool".to_string(),
+            display_name: "Test Tool".to_string(),
+            token_url: "https://example.com/token".to_string(),
+            client_id: "client123".to_string(),
+            client_secret: None,
+            redirect_uri: "https://example.com/oauth/callback".to_string(),
+            code_verifier: None,
+            access_token_field: "access_token".to_string(),
+            secret_name: "test_token".to_string(),
+            provider: None,
+            validation_endpoint: None,
+            scopes: vec![],
+            user_id: "test".to_string(),
+            secrets,
+            sse_sender: None,
+            gateway_token: None,
+            token_exchange_extra_params: std::collections::HashMap::new(),
+            client_id_secret_name: None,
+            created_at,
+        };
+
+        ext_mgr
+            .pending_oauth_flows()
+            .write()
+            .await
+            .insert("test_nonce".to_string(), flow);
+
+        let state = test_gateway_state(Some(ext_mgr.clone()));
+        let app = test_oauth_router(state);
+        let versioned_state =
+            crate::cli::oauth_defaults::encode_hosted_oauth_state("test_nonce", Some("myinstance"));
+
+        let req = axum::http::Request::builder()
+            .uri(format!(
+                "/oauth/callback?code=fake_code&state={}",
+                urlencoding::encode(&versioned_state)
+            ))
+            .body(Body::empty())
+            .expect("request");
+
+        let resp = ServiceExt::<axum::http::Request<Body>>::oneshot(app, req)
+            .await
+            .expect("response");
+        assert_eq!(resp.status(), StatusCode::OK);
+
+        let body = axum::body::to_bytes(resp.into_body(), 1024 * 64)
+            .await
+            .expect("body");
+        let html = String::from_utf8_lossy(&body);
+        assert!(html.contains("Authorization Failed"));
+        assert!(
+            ext_mgr
+                .pending_oauth_flows()
+                .read()
+                .await
+                .get("test_nonce")
+                .is_none()
+        );
+    }
+
    // --- Slack relay OAuth CSRF tests ---

    fn test_relay_oauth_router(state: Arc<GatewayState>) -> Router {
@@ -3391,7 +3688,7 @@ mod tests {

        // Callback without state param should be rejected
        let req = axum::http::Request::builder()
-            .uri("/oauth/slack/callback?stream_token=tok123&team_id=T123&provider=slack")
+            .uri("/oauth/slack/callback?team_id=T123&provider=slack")
            .body(Body::empty())
            .expect("request");

@@ -3435,7 +3732,7 @@ mod tests {

        // Callback with wrong state param
        let req = axum::http::Request::builder()
-            .uri("/oauth/slack/callback?stream_token=tok123&team_id=T123&provider=slack&state=wrong-nonce")
+            .uri("/oauth/slack/callback?team_id=T123&provider=slack&state=wrong-nonce")
            .body(Body::empty())
            .expect("request");

@@ -3483,7 +3780,7 @@ mod tests {
        // we just verify it doesn't return a CSRF error.
        let req = axum::http::Request::builder()
            .uri(format!(
-                "/oauth/slack/callback?stream_token=tok123&team_id=T123&provider=slack&state={}",
+                "/oauth/slack/callback?team_id=T123&provider=slack&state={}",
                nonce
            ))
            .body(Body::empty())
@@ -29,9 +29,15 @@ I18n.register('en', {
  'tab.memory': 'Memory',
  'tab.jobs': 'Jobs',
  'tab.routines': 'Routines',
+  'tab.settings': 'Settings',
  'tab.extensions': 'Extensions',
  'tab.skills': 'Skills',
  'tab.logs': 'Logs',
+  'settings.inference': 'Inference',
+  'settings.agent': 'Agent',
+  'settings.channels': 'Channels',
+  'settings.networking': 'Networking',
+  'settings.mcp': 'MCP',
  
  // Status
  'status.connected': 'Connected',
@@ -131,10 +137,10 @@ I18n.register('en', {
  
  // Extensions Tab
  'extensions.installed': 'Installed Extensions',
-  'extensions.available': 'Available WASM Extensions',
-  'extensions.installWasm': 'Install WASM Extension',
+  'extensions.available': 'Available Extensions',
+  'extensions.installWasm': 'Install Extension',
  'extensions.noInstalled': 'No extensions installed',
-  'extensions.noAvailable': 'No additional WASM extensions available',
+  'extensions.noAvailable': 'No additional extensions available',
  'extensions.loading': 'Loading...',
  'extensions.install': 'Install',
  'extensions.installing': 'Installing...',
@@ -156,13 +162,8 @@ I18n.register('en', {
  'mcp.addCustom': 'Add Custom MCP Server',
  'mcp.add': 'Add',
  'mcp.addedSuccess': 'Added MCP server {name}',
-  
-  // Registered Tools
-  'tools.registered': 'Registered Tools',
-  'tools.name': 'Name',
-  'tools.description': 'Description',
-  'tools.empty': 'No tools registered',
-  
+
+
  // Skills Tab
  'skills.installed': 'Installed Skills',
  'skills.noInstalled': 'No skills installed',
@@ -302,6 +303,7 @@ I18n.register('en', {
  
  // Common
  'common.loading': 'Loading...',
+  'common.loadFailed': 'Failed to load',
  'common.noData': 'No data',
  'common.search': 'Search',
  'common.add': 'Add',
@@ -328,6 +330,8 @@ I18n.register('en', {
  
  // Extensions
  'ext.active': 'Active',
+  'ext.inactive': 'Inactive',
+  'ext.builtin': 'Built-in',
  'ext.remove': 'Remove',
  'ext.install': 'Install',
  'ext.installing': 'Installing...',
@@ -342,10 +346,173 @@ I18n.register('en', {
  
  // Configure
  'config.title': 'Configure {name}',
+  'config.telegramOwnerHint': 'After saving, IronClaw will show a one-time code. Send `/start CODE` to your bot in Telegram and IronClaw will finish setup automatically.',
+  'config.telegramChallengeTitle': 'Telegram owner verification',
+  'config.telegramOwnerWaiting': 'Waiting for Telegram owner verification...',
+  'config.telegramCommandLabel': 'Send this in Telegram:',
+  'config.telegramStartOver': 'Start over',
+  'config.telegramStartOverHint': 'Telegram verification did not complete. Click Start over to generate a new code and try again.',
+  'config.telegramOpenBot': 'Open bot in Telegram',
  'config.optional': ' (optional)',
  'config.alreadySet': '(already set — leave empty to keep)',
  'config.alreadyConfigured': 'Already configured',
  'config.autoGenerate': 'Auto-generated if empty',
  'config.save': 'Save',
  'config.cancel': 'Cancel',
+
+  // Settings toolbar
+  'settings.export': 'Export',
+  'settings.import': 'Import',
+  'settings.searchPlaceholder': 'Search settings...',
+  'settings.exportSuccess': 'Settings exported',
+  'settings.exportFailed': 'Export failed: {message}',
+  'settings.importSuccess': 'Settings imported successfully',
+  'settings.importFailed': 'Import failed: {message}',
+  'settings.restartRequired': 'Restart required for changes to take effect.',
+  'settings.restartNow': 'Restart Now',
+  'settings.noMatchingSettings': 'No settings matching "{query}"',
+  'settings.noSettings': 'No settings found',
+  'settings.saved': 'Saved',
+  'settings.on': 'On',
+  'settings.off': 'Off',
+  'settings.envValue': 'env: {value}',
+  'settings.envDefault': 'env default',
+  'settings.useEnvDefault': 'use env default',
+
+  // Settings groups
+  'cfg.group.llm': 'LLM Provider',
+  'cfg.group.embeddings': 'Embeddings',
+  'cfg.group.agent': 'Agent',
+  'cfg.group.heartbeat': 'Heartbeat',
+  'cfg.group.sandbox': 'Sandbox',
+  'cfg.group.routines': 'Routines',
+  'cfg.group.safety': 'Safety',
+  'cfg.group.skills': 'Skills',
+  'cfg.group.search': 'Search',
+  'cfg.group.tunnel': 'Tunnel',
+  'cfg.group.gateway': 'Gateway',
+
+  // Inference settings
+  'cfg.llm_backend.label': 'Backend',
+  'cfg.llm_backend.desc': 'LLM inference provider',
+  'cfg.selected_model.label': 'Model',
+  'cfg.selected_model.desc': 'Model name or ID for the selected backend',
+  'cfg.ollama_base_url.label': 'Ollama URL',
+  'cfg.ollama_base_url.desc': 'Base URL for Ollama API',
+  'cfg.openai_compatible_base_url.label': 'OpenAI-compatible URL',
+  'cfg.openai_compatible_base_url.desc': 'Base URL for OpenAI-compatible API',
+  'cfg.bedrock_region.label': 'Bedrock Region',
+  'cfg.bedrock_region.desc': 'AWS region for Bedrock',
+  'cfg.bedrock_cross_region.label': 'Cross-Region',
+  'cfg.bedrock_cross_region.desc': 'Enable cross-region inference',
+  'cfg.bedrock_profile.label': 'AWS Profile',
+  'cfg.bedrock_profile.desc': 'AWS profile for Bedrock auth',
+  'cfg.embeddings_enabled.label': 'Enabled',
+  'cfg.embeddings_enabled.desc': 'Enable vector embeddings for memory search',
+  'cfg.embeddings_provider.label': 'Provider',
+  'cfg.embeddings_provider.desc': 'Embeddings API provider',
+  'cfg.embeddings_model.label': 'Model',
+  'cfg.embeddings_model.desc': 'Embedding model name',
+
+  // Agent settings
+  'cfg.agent_name.label': 'Name',
+  'cfg.agent_name.desc': 'Agent display name',
+  'cfg.agent_max_parallel_jobs.label': 'Max Parallel Jobs',
+  'cfg.agent_max_parallel_jobs.desc': 'Maximum concurrent background jobs',
+  'cfg.agent_job_timeout.label': 'Job Timeout',
+  'cfg.agent_job_timeout.desc': 'Max duration per job in seconds',
+  'cfg.agent_max_tool_iterations.label': 'Max Tool Iterations',
+  'cfg.agent_max_tool_iterations.desc': 'Max tool calls per turn',
+  'cfg.agent_use_planning.label': 'Planning',
+  'cfg.agent_use_planning.desc': 'Enable multi-step planning before execution',
+  'cfg.agent_auto_approve.label': 'Auto-approve Tools',
+  'cfg.agent_auto_approve.desc': 'Skip manual approval for tool calls',
+  'cfg.agent_timezone.label': 'Timezone',
+  'cfg.agent_timezone.desc': 'Default timezone (IANA)',
+  'cfg.agent_session_idle.label': 'Session Idle Timeout',
+  'cfg.agent_session_idle.desc': 'Seconds before idle session expires',
+  'cfg.agent_stuck_threshold.label': 'Stuck Threshold',
+  'cfg.agent_stuck_threshold.desc': 'Seconds before a job is considered stuck',
+  'cfg.agent_max_repair.label': 'Max Repair Attempts',
+  'cfg.agent_max_repair.desc': 'Auto-recovery attempts for stuck jobs',
+  'cfg.agent_max_cost.label': 'Max Daily Cost',
+  'cfg.agent_max_cost.desc': 'Daily LLM spend cap in cents (0 = unlimited)',
+  'cfg.agent_max_actions.label': 'Max Actions/Hour',
+  'cfg.agent_max_actions.desc': 'Hourly tool call rate limit (0 = unlimited)',
+  'cfg.agent_allow_local.label': 'Allow Local Tools',
+  'cfg.agent_allow_local.desc': 'Enable local filesystem tool execution',
+
+  // Heartbeat settings
+  'cfg.heartbeat_enabled.label': 'Enabled',
+  'cfg.heartbeat_enabled.desc': 'Run periodic background checks',
+  'cfg.heartbeat_interval.label': 'Interval',
+  'cfg.heartbeat_interval.desc': 'Seconds between heartbeats (default: 1800)',
+  'cfg.heartbeat_notify_channel.label': 'Notify Channel',
+  'cfg.heartbeat_notify_channel.desc': 'Channel to send heartbeat findings to',
+  'cfg.heartbeat_notify_user.label': 'Notify User',
+  'cfg.heartbeat_notify_user.desc': 'User ID to notify',
+  'cfg.heartbeat_quiet_start.label': 'Quiet Hours Start',
+  'cfg.heartbeat_quiet_start.desc': 'Hour (0-23) to stop heartbeats',
+  'cfg.heartbeat_quiet_end.label': 'Quiet Hours End',
+  'cfg.heartbeat_quiet_end.desc': 'Hour (0-23) to resume heartbeats',
+  'cfg.heartbeat_timezone.label': 'Timezone',
+  'cfg.heartbeat_timezone.desc': 'Timezone for quiet hours (IANA)',
+
+  // Sandbox settings
+  'cfg.sandbox_enabled.label': 'Enabled',
+  'cfg.sandbox_enabled.desc': 'Enable Docker sandbox for background jobs',
+  'cfg.sandbox_policy.label': 'Policy',
+  'cfg.sandbox_policy.desc': 'Sandbox security policy',
+  'cfg.sandbox_timeout.label': 'Timeout',
+  'cfg.sandbox_timeout.desc': 'Max job duration in seconds',
+  'cfg.sandbox_memory.label': 'Memory Limit',
+  'cfg.sandbox_memory.desc': 'Container memory limit (MB)',
+  'cfg.sandbox_image.label': 'Docker Image',
+  'cfg.sandbox_image.desc': 'Container image for sandbox jobs',
+
+  // Routines settings
+  'cfg.routines_max_concurrent.label': 'Max Concurrent',
+  'cfg.routines_max_concurrent.desc': 'Maximum routines running simultaneously',
+  'cfg.routines_cooldown.label': 'Default Cooldown',
+  'cfg.routines_cooldown.desc': 'Minimum seconds between routine fires',
+
+  // Safety settings
+  'cfg.safety_max_output.label': 'Max Output Length',
+  'cfg.safety_max_output.desc': 'Maximum output tokens per response',
+  'cfg.safety_injection_check.label': 'Injection Check',
+  'cfg.safety_injection_check.desc': 'Enable prompt injection detection',
+
+  // Skills settings
+  'cfg.skills_max_active.label': 'Max Active Skills',
+  'cfg.skills_max_active.desc': 'Maximum skills active simultaneously',
+  'cfg.skills_max_tokens.label': 'Max Context Tokens',
+  'cfg.skills_max_tokens.desc': 'Token budget for skill prompts',
+
+  // Search settings
+  'cfg.search_fusion.label': 'Fusion Strategy',
+  'cfg.search_fusion.desc': 'Hybrid search ranking method',
+
+  // Networking settings
+  'cfg.tunnel_provider.label': 'Provider',
+  'cfg.tunnel_provider.desc': 'Public URL tunnel provider',
+  'cfg.tunnel_public_url.label': 'Public URL',
+  'cfg.tunnel_public_url.desc': 'Static public URL (if not using tunnel provider)',
+  'cfg.gateway_rate_limit.label': 'Rate Limit',
+  'cfg.gateway_rate_limit.desc': 'Max chat messages per minute',
+  'cfg.gateway_max_connections.label': 'Max Connections',
+  'cfg.gateway_max_connections.desc': 'Max simultaneous SSE/WS connections',
+
+  // Channels subtab
+  'channels.builtin': 'Built-in Channels',
+  'channels.messaging': 'Messaging Channels',
+  'channels.webGateway': 'Web Gateway',
+  'channels.webGatewayDesc': 'Browser-based chat interface',
+  'channels.httpWebhook': 'HTTP Webhook',
+  'channels.httpWebhookDesc': 'Incoming webhook endpoint for external integrations',
+  'channels.cli': 'CLI',
+  'channels.cliDesc': 'Terminal UI with Ratatui',
+  'channels.repl': 'REPL',
+  'channels.replDesc': 'Simple read-eval-print loop for testing',
+  'channels.configureVia': 'Configure via {env}',
+  'channels.runWith': 'Run with: {cmd}',
 });
@@ -29,9 +29,15 @@ I18n.register('zh-CN', {
  'tab.memory': '记忆',
  'tab.jobs': '任务',
  'tab.routines': '定时任务',
+  'tab.settings': '设置',
  'tab.extensions': '扩展',
  'tab.skills': '技能',
  'tab.logs': '日志',
+  'settings.inference': '推理',
+  'settings.agent': '代理',
+  'settings.channels': '频道',
+  'settings.networking': '网络',
+  'settings.mcp': 'MCP',
  
  // 状态
  'status.connected': '已连接',
@@ -131,10 +137,10 @@ I18n.register('zh-CN', {
  
  // 扩展标签页
  'extensions.installed': '已安装扩展',
-  'extensions.available': '可用 WASM 扩展',
-  'extensions.installWasm': '安装 WASM 扩展',
+  'extensions.available': '可用扩展',
+  'extensions.installWasm': '安装扩展',
  'extensions.noInstalled': '没有安装扩展',
-  'extensions.noAvailable': '没有其他可用的 WASM 扩展',
+  'extensions.noAvailable': '没有其他可用扩展',
  'extensions.loading': '加载中...',
  'extensions.install': '安装',
  'extensions.installing': '安装中...',
@@ -156,13 +162,8 @@ I18n.register('zh-CN', {
  'mcp.addCustom': '添加自定义 MCP 服务器',
  'mcp.add': '添加',
  'mcp.addedSuccess': '已添加 MCP 服务器 {name}',
-  
-  // 注册工具
-  'tools.registered': '注册工具',
-  'tools.name': '名称',
-  'tools.description': '描述',
-  'tools.empty': '没有注册工具',
-  
+
+
  // 技能标签页
  'skills.installed': '已安装技能',
  'skills.noInstalled': '没有安装技能',
@@ -302,6 +303,7 @@ I18n.register('zh-CN', {
  
  // 通用
  'common.loading': '加载中...',
+  'common.loadFailed': '加载失败',
  'common.noData': '暂无数据',
  'common.search': '搜索',
  'common.add': '添加',
@@ -328,6 +330,8 @@ I18n.register('zh-CN', {
  
  // 扩展
  'ext.active': '已激活',
+  'ext.inactive': '未激活',
+  'ext.builtin': '内置',
  'ext.remove': '移除',
  'ext.install': '安装',
  'ext.installing': '安装中...',
@@ -342,10 +346,172 @@ I18n.register('zh-CN', {
  
  // 配置
  'config.title': '配置 {name}',
+  'config.telegramOwnerHint': '保存后，IronClaw 会显示一次性验证码。将 `/start CODE` 发送给你的 Telegram 机器人，IronClaw 会自动完成设置。',
+  'config.telegramChallengeTitle': 'Telegram 所有者验证',
+  'config.telegramOwnerWaiting': '正在等待 Telegram 所有者验证...',
+  'config.telegramCommandLabel': '请在 Telegram 中发送：',
+  'config.telegramStartOver': '重新开始',
+  'config.telegramStartOverHint': 'Telegram 验证未完成。点击“重新开始”以生成新的验证码并重试。',
  'config.optional': '（可选）',
  'config.alreadySet': '（已设置 — 留空以保持不变）',
  'config.alreadyConfigured': '已配置',
  'config.autoGenerate': '如果为空则自动生成',
  'config.save': '保存',
  'config.cancel': '取消',
+
+  // 设置工具栏
+  'settings.export': '导出',
+  'settings.import': '导入',
+  'settings.searchPlaceholder': '搜索设置...',
+  'settings.exportSuccess': '设置已导出',
+  'settings.exportFailed': '导出失败: {message}',
+  'settings.importSuccess': '设置导入成功',
+  'settings.importFailed': '导入失败: {message}',
+  'settings.restartRequired': '需要重启才能使更改生效。',
+  'settings.restartNow': '立即重启',
+  'settings.noMatchingSettings': '没有匹配 "{query}" 的设置',
+  'settings.noSettings': '未找到设置',
+  'settings.saved': '已保存',
+  'settings.on': '开启',
+  'settings.off': '关闭',
+  'settings.envValue': '环境变量: {value}',
+  'settings.envDefault': '使用环境变量默认值',
+  'settings.useEnvDefault': '使用环境变量默认值',
+
+  // 设置分组
+  'cfg.group.llm': 'LLM 提供商',
+  'cfg.group.embeddings': '嵌入向量',
+  'cfg.group.agent': '代理',
+  'cfg.group.heartbeat': '心跳',
+  'cfg.group.sandbox': '沙箱',
+  'cfg.group.routines': '定时任务',
+  'cfg.group.safety': '安全',
+  'cfg.group.skills': '技能',
+  'cfg.group.search': '搜索',
+  'cfg.group.tunnel': '隧道',
+  'cfg.group.gateway': '网关',
+
+  // 推理设置
+  'cfg.llm_backend.label': '后端',
+  'cfg.llm_backend.desc': 'LLM 推理提供商',
+  'cfg.selected_model.label': '模型',
+  'cfg.selected_model.desc': '所选后端的模型名称或 ID',
+  'cfg.ollama_base_url.label': 'Ollama URL',
+  'cfg.ollama_base_url.desc': 'Ollama API 基础 URL',
+  'cfg.openai_compatible_base_url.label': 'OpenAI 兼容 URL',
+  'cfg.openai_compatible_base_url.desc': 'OpenAI 兼容 API 基础 URL',
+  'cfg.bedrock_region.label': 'Bedrock 区域',
+  'cfg.bedrock_region.desc': 'Bedrock 的 AWS 区域',
+  'cfg.bedrock_cross_region.label': '跨区域',
+  'cfg.bedrock_cross_region.desc': '启用跨区域推理',
+  'cfg.bedrock_profile.label': 'AWS 配置文件',
+  'cfg.bedrock_profile.desc': 'Bedrock 认证的 AWS 配置文件',
+  'cfg.embeddings_enabled.label': '启用',
+  'cfg.embeddings_enabled.desc': '启用向量嵌入以支持记忆搜索',
+  'cfg.embeddings_provider.label': '提供商',
+  'cfg.embeddings_provider.desc': '嵌入向量 API 提供商',
+  'cfg.embeddings_model.label': '模型',
+  'cfg.embeddings_model.desc': '嵌入向量模型名称',
+
+  // 代理设置
+  'cfg.agent_name.label': '名称',
+  'cfg.agent_name.desc': '代理显示名称',
+  'cfg.agent_max_parallel_jobs.label': '最大并行任务数',
+  'cfg.agent_max_parallel_jobs.desc': '最大并发后台任务数',
+  'cfg.agent_job_timeout.label': '任务超时',
+  'cfg.agent_job_timeout.desc': '每个任务的最大持续时间（秒）',
+  'cfg.agent_max_tool_iterations.label': '最大工具迭代次数',
+  'cfg.agent_max_tool_iterations.desc': '每轮最大工具调用次数',
+  'cfg.agent_use_planning.label': '规划',
+  'cfg.agent_use_planning.desc': '执行前启用多步规划',
+  'cfg.agent_auto_approve.label': '自动批准工具',
+  'cfg.agent_auto_approve.desc': '跳过工具调用的手动审批',
+  'cfg.agent_timezone.label': '时区',
+  'cfg.agent_timezone.desc': '默认时区（IANA）',
+  'cfg.agent_session_idle.label': '会话空闲超时',
+  'cfg.agent_session_idle.desc': '空闲会话过期前的秒数',
+  'cfg.agent_stuck_threshold.label': '卡住阈值',
+  'cfg.agent_stuck_threshold.desc': '任务被认为卡住前的秒数',
+  'cfg.agent_max_repair.label': '最大修复尝试次数',
+  'cfg.agent_max_repair.desc': '卡住任务的自动恢复尝试次数',
+  'cfg.agent_max_cost.label': '每日最大费用',
+  'cfg.agent_max_cost.desc': '每日 LLM 支出上限（美分，0 = 无限制）',
+  'cfg.agent_max_actions.label': '每小时最大操作数',
+  'cfg.agent_max_actions.desc': '每小时工具调用速率限制（0 = 无限制）',
+  'cfg.agent_allow_local.label': '允许本地工具',
+  'cfg.agent_allow_local.desc': '启用本地文件系统工具执行',
+
+  // 心跳设置
+  'cfg.heartbeat_enabled.label': '启用',
+  'cfg.heartbeat_enabled.desc': '运行定期后台检查',
+  'cfg.heartbeat_interval.label': '间隔',
+  'cfg.heartbeat_interval.desc': '心跳间隔秒数（默认：1800）',
+  'cfg.heartbeat_notify_channel.label': '通知频道',
+  'cfg.heartbeat_notify_channel.desc': '发送心跳发现的频道',
+  'cfg.heartbeat_notify_user.label': '通知用户',
+  'cfg.heartbeat_notify_user.desc': '要通知的用户 ID',
+  'cfg.heartbeat_quiet_start.label': '静默时段开始',
+  'cfg.heartbeat_quiet_start.desc': '停止心跳的小时（0-23）',
+  'cfg.heartbeat_quiet_end.label': '静默时段结束',
+  'cfg.heartbeat_quiet_end.desc': '恢复心跳的小时（0-23）',
+  'cfg.heartbeat_timezone.label': '时区',
+  'cfg.heartbeat_timezone.desc': '静默时段的时区（IANA）',
+
+  // 沙箱设置
+  'cfg.sandbox_enabled.label': '启用',
+  'cfg.sandbox_enabled.desc': '启用 Docker 沙箱以运行后台任务',
+  'cfg.sandbox_policy.label': '策略',
+  'cfg.sandbox_policy.desc': '沙箱安全策略',
+  'cfg.sandbox_timeout.label': '超时',
+  'cfg.sandbox_timeout.desc': '最大任务持续时间（秒）',
+  'cfg.sandbox_memory.label': '内存限制',
+  'cfg.sandbox_memory.desc': '容器内存限制（MB）',
+  'cfg.sandbox_image.label': 'Docker 镜像',
+  'cfg.sandbox_image.desc': '沙箱任务的容器镜像',
+
+  // 定时任务设置
+  'cfg.routines_max_concurrent.label': '最大并发数',
+  'cfg.routines_max_concurrent.desc': '同时运行的最大定时任务数',
+  'cfg.routines_cooldown.label': '默认冷却时间',
+  'cfg.routines_cooldown.desc': '定时任务触发间的最小秒数',
+
+  // 安全设置
+  'cfg.safety_max_output.label': '最大输出长度',
+  'cfg.safety_max_output.desc': '每次响应的最大输出令牌数',
+  'cfg.safety_injection_check.label': '注入检查',
+  'cfg.safety_injection_check.desc': '启用提示注入检测',
+
+  // 技能设置
+  'cfg.skills_max_active.label': '最大活跃技能数',
+  'cfg.skills_max_active.desc': '同时活跃的最大技能数',
+  'cfg.skills_max_tokens.label': '最大上下文令牌数',
+  'cfg.skills_max_tokens.desc': '技能提示的令牌预算',
+
+  // 搜索设置
+  'cfg.search_fusion.label': '融合策略',
+  'cfg.search_fusion.desc': '混合搜索排名方法',
+
+  // 网络设置
+  'cfg.tunnel_provider.label': '提供商',
+  'cfg.tunnel_provider.desc': '公网 URL 隧道提供商',
+  'cfg.tunnel_public_url.label': '公网 URL',
+  'cfg.tunnel_public_url.desc': '静态公网 URL（不使用隧道提供商时）',
+  'cfg.gateway_rate_limit.label': '速率限制',
+  'cfg.gateway_rate_limit.desc': '每分钟最大聊天消息数',
+  'cfg.gateway_max_connections.label': '最大连接数',
+  'cfg.gateway_max_connections.desc': '最大同时 SSE/WS 连接数',
+
+  // 频道子标签
+  'channels.builtin': '内置频道',
+  'channels.messaging': '消息频道',
+  'channels.webGateway': 'Web 网关',
+  'channels.webGatewayDesc': '基于浏览器的聊天界面',
+  'channels.httpWebhook': 'HTTP Webhook',
+  'channels.httpWebhookDesc': '用于外部集成的传入 webhook 端点',
+  'channels.cli': 'CLI',
+  'channels.cliDesc': '使用 Ratatui 的终端 UI',
+  'channels.repl': 'REPL',
+  'channels.replDesc': '用于测试的简单读取-求值-打印循环',
+  'channels.configureVia': '通过 {env} 配置',
+  'channels.runWith': '运行命令: {cmd}',
 });
@@ -95,8 +95,7 @@
      <button data-tab="memory" data-i18n="tab.memory">Memory</button>
      <button data-tab="jobs" data-i18n="tab.jobs">Jobs</button>
      <button data-tab="routines" data-i18n="tab.routines">Routines</button>
-      <button data-tab="extensions" data-i18n="tab.extensions">Extensions</button>
-      <button data-tab="skills" data-i18n="tab.skills">Skills</button>
+      <button data-tab="settings" data-i18n="tab.settings">Settings</button>
      <div class="spacer"></div>

      <!-- Language Switcher -->
@@ -271,77 +270,125 @@
      </div>
    </div>

-    <!-- Extensions Tab -->
-    <div class="tab-panel" id="tab-extensions">
-      <div class="extensions-container">
-        <div class="extensions-section">
-          <h3 data-i18n="extensions.installed">Installed Extensions</h3>
-          <div class="extensions-list" id="extensions-list">
-            <div class="empty-state" data-i18n="common.loading">Loading...</div>
-          </div>
+    <!-- Settings Tab -->
+    <div class="tab-panel" id="tab-settings">
+      <div class="settings-layout">
+        <div class="settings-sidebar">
+          <button class="settings-subtab active" data-settings-subtab="inference" data-i18n="settings.inference">Inference</button>
+          <button class="settings-subtab" data-settings-subtab="agent" data-i18n="settings.agent">Agent</button>
+          <button class="settings-subtab" data-settings-subtab="channels" data-i18n="settings.channels">Channels</button>
+          <button class="settings-subtab" data-settings-subtab="networking" data-i18n="settings.networking">Networking</button>
+          <button class="settings-subtab" data-settings-subtab="extensions" data-i18n="tab.extensions">Extensions</button>
+          <button class="settings-subtab" data-settings-subtab="mcp" data-i18n="settings.mcp">MCP</button>
+          <button class="settings-subtab" data-settings-subtab="skills" data-i18n="tab.skills">Skills</button>
        </div>
-        <div class="extensions-section" id="available-wasm-section">
-          <h3 data-i18n="extensions.available">Available WASM Extensions</h3>
-          <div class="extensions-list" id="available-wasm-list">
-            <div class="empty-state" data-i18n="common.loading">Loading...</div>
+        <div class="settings-content">
+          <div class="settings-toolbar">
+            <div class="settings-search">
+              <input type="text" id="settings-search-input" data-i18n-placeholder="settings.searchPlaceholder" placeholder="Search settings..." data-i18n-attr="aria-label" data-i18n="settings.searchPlaceholder" aria-label="Search settings...">
+            </div>
+            <button id="settings-export-btn" class="settings-toolbar-btn" data-i18n="settings.export">Export</button>
+            <button id="settings-import-btn" class="settings-toolbar-btn" data-i18n="settings.import">Import</button>
          </div>
-        </div>
-        <div class="extensions-section">
-          <h3 data-i18n="extensions.installWasm">Install WASM Extension</h3>
-          <div class="ext-install-form">
-            <input type="text" id="wasm-install-name" data-i18n-placeholder="common.name" placeholder="Extension name">
-            <input type="text" id="wasm-install-url" placeholder="URL to .tar.gz bundle">
-            <button id="wasm-install-btn" data-i18n="extensions.install">Install</button>
+          <div class="settings-subpanel active" id="settings-inference">
+            <div class="extensions-container" id="settings-inference-content">
+              <div class="empty-state" data-i18n="common.loading">Loading settings...</div>
+            </div>
          </div>
-        </div>
-        <div class="extensions-section">
-          <h3 data-i18n="mcp.servers">MCP Servers</h3>
-          <div class="extensions-list" id="mcp-servers-list">
-            <div class="empty-state" data-i18n="common.loading">Loading...</div>
+          <div class="settings-subpanel" id="settings-agent">
+            <div class="extensions-container" id="settings-agent-content">
+              <div class="empty-state" data-i18n="common.loading">Loading settings...</div>
+            </div>
          </div>
-          <h4 data-i18n="mcp.addCustom">Add Custom MCP Server</h4>
-          <div class="ext-install-form">
-            <input type="text" id="mcp-install-name" data-i18n-placeholder="common.name" placeholder="Server name">
-            <input type="text" id="mcp-install-url" placeholder="MCP server URL (https://...)">
-            <button id="mcp-add-btn" data-i18n="mcp.add">Add</button>
+          <div class="settings-subpanel" id="settings-channels">
+            <div class="extensions-container" id="settings-channels-content">
+              <div class="empty-state" data-i18n="common.loading">Loading channels...</div>
+            </div>
+          </div>
+          <div class="settings-subpanel" id="settings-networking">
+            <div class="extensions-container" id="settings-networking-content">
+              <div class="empty-state" data-i18n="common.loading">Loading...</div>
+            </div>
+          </div>
+          <div class="settings-subpanel" id="settings-extensions">
+            <div class="extensions-container">
+              <div class="extensions-section">
+                <h3 data-i18n="extensions.installed">Installed Extensions</h3>
+                <div class="extensions-list" id="extensions-list">
+                  <div class="empty-state" data-i18n="common.loading">Loading...</div>
+                </div>
+              </div>
+              <div class="extensions-section" id="available-wasm-section">
+                <h3 data-i18n="extensions.available">Available Extensions</h3>
+                <div class="extensions-list" id="available-wasm-list">
+                  <div class="empty-state" data-i18n="common.loading">Loading...</div>
+                </div>
+              </div>
+              <div class="extensions-section">
+                <h3 data-i18n="extensions.installWasm">Install Extension</h3>
+                <div class="ext-install-form">
+                  <input type="text" id="wasm-install-name" data-i18n-placeholder="common.name" placeholder="Extension name">
+                  <input type="text" id="wasm-install-url" placeholder="URL to .tar.gz bundle">
+                  <button id="wasm-install-btn" data-i18n="extensions.install">Install</button>
+                </div>
+              </div>
+            </div>
+          </div>
+          <div class="settings-subpanel" id="settings-mcp">
+            <div class="extensions-container">
+              <div class="extensions-section">
+                <h3 data-i18n="mcp.servers">MCP Servers</h3>
+                <div class="extensions-list" id="mcp-servers-list">
+                  <div class="empty-state" data-i18n="common.loading">Loading...</div>
+                </div>
+                <h4 data-i18n="mcp.addCustom">Add Custom MCP Server</h4>
+                <div class="ext-install-form">
+                  <input type="text" id="mcp-install-name" data-i18n-placeholder="common.name" placeholder="Server name">
+                  <input type="text" id="mcp-install-url" placeholder="MCP server URL (https://...)">
+                  <button id="mcp-add-btn" data-i18n="mcp.add">Add</button>
+                </div>
+              </div>
+            </div>
+          </div>
+          <div class="settings-subpanel" id="settings-skills">
+            <div class="extensions-container">
+              <div class="extensions-section">
+                <h3 data-i18n="skills.searchClawHub">Search ClawHub</h3>
+                <div class="skill-search-box">
+                  <input type="text" id="skill-search-input" data-i18n-placeholder="skills.searchPlaceholder" placeholder="Search for skills...">
+                  <button id="skill-search-btn" data-i18n="skills.search">Search</button>
+                </div>
+                <div class="extensions-list" id="skill-search-results"></div>
+              </div>
+              <div class="extensions-section">
+                <h3 data-i18n="skills.installed">Installed Skills</h3>
+                <div class="extensions-list" id="skills-list">
+                  <div class="empty-state" data-i18n="skills.loading">Loading skills...</div>
+                </div>
+              </div>
+              <div class="extensions-section">
+                <h3 data-i18n="skills.installByUrl">Install Skill by URL</h3>
+                <div class="ext-install-form">
+                  <input type="text" id="skill-install-name" data-i18n-placeholder="skills.namePlaceholder" placeholder="Skill name or slug">
+                  <input type="text" id="skill-install-url" data-i18n-placeholder="skills.urlPlaceholder" placeholder="HTTPS URL to SKILL.md (optional)">
+                  <button id="skill-install-btn" data-i18n="extensions.install">Install</button>
+                </div>
+              </div>
+            </div>
          </div>
-        </div>
-        <div class="extensions-section">
-          <h3 data-i18n="tools.registered">Registered Tools</h3>
-          <table class="tools-table" id="tools-table">
-            <thead><tr><th data-i18n="tools.name">Name</th><th data-i18n="tools.description">Description</th></tr></thead>
-            <tbody id="tools-tbody"></tbody>
-          </table>
-          <div class="empty-state" id="tools-empty" style="display:none" data-i18n="tools.empty">No tools registered</div>
        </div>
      </div>
    </div>
+  </div>

-    <!-- Skills Tab -->
-    <div class="tab-panel" id="tab-skills">
-      <div class="extensions-container">
-        <div class="extensions-section">
-          <h3 data-i18n="skills.searchClawHub">Search ClawHub</h3>
-          <div class="skill-search-box">
-            <input type="text" id="skill-search-input" data-i18n-placeholder="skills.searchPlaceholder" placeholder="Search...">
-            <button id="skill-search-btn" data-i18n="skills.search">Search</button>
-          </div>
-          <div class="extensions-list" id="skill-search-results"></div>
-        </div>
-        <div class="extensions-section">
-          <h3 data-i18n="skills.installed">Installed Skills</h3>
-          <div class="extensions-list" id="skills-list">
-            <div class="empty-state" data-i18n="skills.loading">Loading skills...</div>
-          </div>
-        </div>
-        <div class="extensions-section">
-          <h3 data-i18n="skills.installByUrl">Install Skill by URL</h3>
-          <div class="ext-install-form">
-            <input type="text" id="skill-install-name" data-i18n-placeholder="skills.namePlaceholder" placeholder="Skill name or slug">
-            <input type="text" id="skill-install-url" data-i18n-placeholder="skills.urlPlaceholder" placeholder="HTTPS URL to SKILL.md (optional)">
-            <button id="skill-install-btn" data-i18n="extensions.install">Install</button>
-          </div>
-        </div>
+  <!-- Confirmation Modal -->
+  <div id="confirm-modal" class="modal-overlay" style="display:none" role="dialog" aria-modal="true" aria-labelledby="confirm-modal-title">
+    <div class="modal">
+      <h3 id="confirm-modal-title"></h3>
+      <p id="confirm-modal-message"></p>
+      <div class="modal-actions">
+        <button id="confirm-modal-cancel-btn" class="btn-secondary" data-i18n="btn.cancel">Cancel</button>
+        <button id="confirm-modal-btn" class="btn-danger">Confirm</button>
      </div>
    </div>
  </div>
@@ -18,6 +18,12 @@
  --radius-lg: 12px;
  --shadow: 0 2px 8px rgba(0, 0, 0, 0.4);
  --font-mono: 'IBM Plex Mono', 'SF Mono', 'Fira Code', Consolas, monospace;
+  --text-muted: #71717a;
+  --bg-hover: rgba(255, 255, 255, 0.03);
+  --danger-soft: rgba(230, 76, 76, 0.15);
+  --warning-soft: rgba(245, 166, 35, 0.15);
+  --transition-fast: 150ms ease;
+  --transition-base: 0.2s ease;
 }

 * {
@@ -332,10 +338,10 @@ body {
 .restart-loader-content {
  position: relative;
  z-index: 10000;
-  background-color: #1a1a1a;
-  border: 1px solid #333;
+  background-color: var(--bg-secondary);
+  border: 1px solid var(--border);
  border-radius: 0.75rem;
-  box-shadow: 0 25px 50px -12px rgba(0, 0, 0, 0.25);
+  box-shadow: 0 25px 50px -12px rgba(0, 0, 0, 0.5);
  width: 100%;
  max-width: 28rem;
  margin: 0 1rem;
@@ -352,7 +358,7 @@ body {
 }

 .restart-title {
-  color: #e0e0e0;
+  color: var(--text);
  font-size: 0.85rem;
  margin-bottom: 1rem;
  margin-top: 0;
@@ -388,10 +394,10 @@ body {
 .restart-modal-content {
  position: relative;
  z-index: 10000;
-  background-color: #1a1a1a;
-  border: 1px solid #333;
+  background-color: var(--bg-secondary);
+  border: 1px solid var(--border);
  border-radius: 0.75rem;
-  box-shadow: 0 25px 50px -12px rgba(0, 0, 0, 0.25);
+  box-shadow: 0 25px 50px -12px rgba(0, 0, 0, 0.5);
  width: 100%;
  max-width: 28rem;
  margin: 0 1rem;
@@ -403,11 +409,11 @@ body {
  align-items: center;
  justify-content: space-between;
  padding: 1rem 1.25rem;
-  border-bottom: 1px solid #2a2a2a;
+  border-bottom: 1px solid var(--border);
 }

 .restart-modal-header h2 {
-  color: #e0e0e0;
+  color: var(--text);
  font-size: 0.95rem;
  margin: 0;
 }
@@ -426,8 +432,8 @@ body {
 }

 .restart-modal-close:hover {
-  color: #ccc;
-  background-color: #2a2a2a;
+  color: var(--text-secondary);
+  background-color: var(--bg-tertiary);
 }

 .restart-modal-body {
@@ -435,21 +441,21 @@ body {
 }

 .restart-modal-description {
-  color: #aaa;
+  color: var(--text-secondary);
  font-size: 0.85rem;
  margin: 0;
 }

 .restart-modal-warning {
  margin-top: 1rem;
-  background-color: #1e1400;
-  border: 1px solid #3a2a00;
+  background-color: var(--warning-soft);
+  border: 1px solid rgba(245, 166, 35, 0.25);
  border-radius: 0.5rem;
  padding: 0.75rem 1rem;
 }

 .restart-modal-warning p {
-  color: #facc15;
+  color: var(--warning);
  font-size: 0.8rem;
  margin: 0;
 }
@@ -460,7 +466,7 @@ body {
  justify-content: flex-end;
  gap: 0.75rem;
  padding: 1rem 1.25rem;
-  border-top: 1px solid #2a2a2a;
+  border-top: 1px solid var(--border);
 }

 .restart-modal-btn {
@@ -473,28 +479,28 @@ body {
 }

 .restart-modal-btn.cancel {
-  color: #ccc;
+  color: var(--text-secondary);
  background-color: transparent;
 }

 .restart-modal-btn.cancel:hover {
-  background-color: #2a2a2a;
+  background-color: var(--bg-tertiary);
 }

 .restart-modal-btn.confirm {
-  background-color: #00D894;
-  color: #111;
+  background-color: var(--accent);
+  color: #09090b;
 }

 .restart-modal-btn.confirm:hover {
-  background-color: #00be82;
+  background-color: var(--accent-hover);
 }

 /* Progress Bar for Restart */
 .restart-progress-bar {
  width: 100%;
  height: 0.375rem;
-  background-color: #2a2a2a;
+  background-color: var(--bg-tertiary);
  border-radius: 9999px;
  overflow: hidden;
 }
@@ -502,7 +508,7 @@ body {
 .restart-progress-fill {
  height: 100%;
  border-radius: 9999px;
-  background-color: #00D894;
+  background-color: var(--accent);
  width: 40%;
  animation: indeterminate 1.5s ease-in-out infinite;
 }
@@ -523,14 +529,14 @@ body {
 }

 .restart-modal-info {
-  color: #666;
+  color: var(--text-secondary);
  font-size: 0.8rem;
  margin-top: 1.25rem;
  margin-bottom: 0;
 }

 .restart-modal-info a {
-  color: #00D894;
+  color: var(--accent);
  text-decoration: none;
 }

@@ -2522,17 +2528,21 @@ body {
 }

 .extensions-section h3 {
-  font-size: 15px;
+  font-size: 11px;
  font-weight: 600;
  margin-bottom: 12px;
-  color: var(--text);
+  color: var(--text-secondary);
+  text-transform: uppercase;
+  letter-spacing: 0.05em;
 }

 .extensions-section h4 {
-  font-size: 13px;
+  font-size: 11px;
  font-weight: 600;
  margin: 16px 0 8px;
-  color: var(--text-secondary);
+  color: var(--text-muted);
+  text-transform: uppercase;
+  letter-spacing: 0.05em;
 }

 .extensions-list {
@@ -2544,12 +2554,29 @@ body {
 .ext-card {
  background: var(--bg-secondary);
  border: 1px solid var(--border);
+  border-left: 3px solid transparent;
  border-radius: var(--radius-lg);
  padding: 14px;
  display: flex;
  flex-direction: column;
  gap: 8px;
-  transition: border-color 0.2s, transform 0.2s;
+  transition: border-color var(--transition-base), box-shadow var(--transition-base), transform 0.2s;
+}
+
+.ext-card.state-active {
+  border-left-color: var(--success);
+}
+
+.ext-card.state-inactive {
+  border-left-color: var(--text-muted);
+}
+
+.ext-card.state-error {
+  border-left-color: var(--danger);
+}
+
+.ext-card.state-pairing {
+  border-left-color: var(--warning);
 }

 .ext-card:hover {
@@ -2592,6 +2619,11 @@ body {
  color: var(--warning);
 }

+.ext-kind.kind-builtin {
+  background: rgba(161, 161, 170, 0.15);
+  color: var(--text-secondary);
+}
+
 .ext-version {
  font-size: 11px;
  color: var(--text-muted);
@@ -2767,13 +2799,20 @@ body {
  border-radius: var(--radius);
  cursor: pointer;
  font-size: 12px;
+  font-weight: 500;
  border: 1px solid var(--border);
  background: var(--bg-tertiary);
  color: var(--text);
+  transition: all var(--transition-fast);
 }

 .btn-ext:hover {
  background: var(--border);
+  transform: translateY(-1px);
+}
+
+.btn-ext:active {
+  transform: scale(0.97);
 }

 .btn-ext.activate {
@@ -2873,6 +2912,7 @@ body {
  width: 100%;
  height: 100%;
  background: rgba(0, 0, 0, 0.6);
+  backdrop-filter: blur(4px);
  z-index: 1000;
  display: flex;
  align-items: center;
@@ -2893,9 +2933,87 @@ body {
 .configure-modal h3 {
  margin: 0 0 16px 0;
  font-size: 16px;
+  color: var(--text);
+}
+
+.configure-hint {
+  margin: 0 0 16px 0;
+  padding: 10px 12px;
+  border-radius: 8px;
+  background: var(--bg-secondary);
+  border: 1px solid var(--border);
+  color: var(--text-secondary);
+  font-size: 13px;
+  line-height: 1.5;
+}
+
+.configure-verification {
+  display: flex;
+  flex-direction: column;
+  gap: 10px;
+  margin: 16px 0 0 0;
+  padding: 12px;
+  border-radius: 8px;
+  background: var(--bg-secondary);
+  border: 1px solid var(--border);
+}
+
+.configure-verification-title {
+  font-size: 13px;
+  font-weight: 600;
  color: var(--text-primary);
 }

+.configure-verification-instructions {
+  font-size: 13px;
+  line-height: 1.5;
+  color: var(--text-secondary);
+}
+
+.configure-verification-code {
+  display: inline-block;
+  width: fit-content;
+  padding: 6px 10px;
+  border-radius: 6px;
+  background: rgba(255, 255, 255, 0.06);
+  border: 1px solid var(--border);
+  color: var(--text-primary);
+  font-size: 13px;
+}
+
+.configure-verification-link {
+  width: fit-content;
+  color: var(--accent, var(--text-link, #4ea3ff));
+  font-size: 13px;
+  text-decoration: none;
+}
+
+.configure-verification-link:hover {
+  text-decoration: underline;
+}
+
+.configure-inline-error {
+  margin: 16px 0 0 0;
+  padding: 10px 12px;
+  border-radius: 8px;
+  background: rgba(220, 38, 38, 0.12);
+  border: 1px solid rgba(220, 38, 38, 0.35);
+  color: #fca5a5;
+  font-size: 13px;
+  line-height: 1.5;
+}
+
+.configure-inline-status {
+  margin: 16px 0 0 0;
+  padding: 10px 12px;
+  border-radius: 8px;
+  background: var(--bg-secondary);
+  border: 1px solid var(--border);
+  color: var(--text-secondary);
+  font-size: 13px;
+  line-height: 1.5;
+}
+
 .configure-form {
  display: flex;
  flex-direction: column;
@@ -2958,31 +3076,6 @@ body {
  justify-content: flex-end;
 }

-.tools-table {
-  width: 100%;
-  border-collapse: collapse;
-}
-
-.tools-table th,
-.tools-table td {
-  padding: 8px 12px;
-  text-align: left;
-  border-bottom: 1px solid var(--border);
-  font-size: 13px;
-}
-
-.tools-table th {
-  color: var(--text-secondary);
-  font-weight: 500;
-  text-transform: uppercase;
-  font-size: 11px;
-  letter-spacing: 0.5px;
-}
-
-.tools-table tr:hover td {
-  background: rgba(255, 255, 255, 0.03);
-}
-
 /* --- Activity tab (unified sandbox job events) --- */

 .activity-terminal {
@@ -3636,10 +3729,14 @@ mark {
  gap: 8px;
  align-items: center;
  flex-wrap: wrap;
+  background: var(--bg-secondary);
+  border: 1px solid var(--border);
+  border-radius: var(--radius-lg);
+  padding: 14px;
 }

 .ext-install-form input {
-  padding: 6px 10px;
+  padding: 8px 12px;
  background: var(--bg);
  border: 1px solid var(--border);
  border-radius: var(--radius);
@@ -3681,6 +3778,10 @@ mark {
  gap: 8px;
  align-items: center;
  margin-bottom: 12px;
+  background: var(--bg-secondary);
+  border: 1px solid var(--border);
+  border-radius: var(--radius-lg);
+  padding: 14px;
 }

 .skill-search-box input {
@@ -3717,10 +3818,10 @@ mark {
 }

 .skill-trust {
-  font-size: 10px;
-  padding: 2px 6px;
-  border-radius: 8px;
-  font-weight: 500;
+  font-size: 11px;
+  padding: 3px 8px;
+  border-radius: 9999px;
+  font-weight: 600;
  text-transform: uppercase;
  letter-spacing: 0.3px;
 }
@@ -3864,6 +3965,27 @@ mark {
    border-bottom: 1px solid var(--border);
  }

+  /* Settings layout: horizontal subtabs on mobile */
+  .settings-layout { flex-direction: column; }
+  .settings-sidebar {
+    width: 100%;
+    flex-direction: row;
+    overflow-x: auto;
+    border-right: none;
+    border-bottom: 1px solid var(--border);
+    padding: 0;
+  }
+  .settings-subtab {
+    border-left: none;
+    border-bottom: 2px solid transparent;
+    white-space: nowrap;
+    padding: 8px 16px;
+  }
+  .settings-subtab.active {
+    border-left-color: transparent;
+    border-bottom-color: var(--accent);
+  }
+
  /* Extension install form */
  .ext-install-form {
    flex-direction: column;
@@ -3890,6 +4012,238 @@ mark {
  }
 }

+/* --- Settings Tab Layout --- */
+.settings-layout {
+  flex: 1;
+  display: flex;
+  overflow: hidden;
+}
+
+.settings-sidebar {
+  width: 180px;
+  border-right: 1px solid var(--border);
+  display: flex;
+  flex-direction: column;
+  background: var(--bg-secondary);
+  padding: 12px 0;
+  flex-shrink: 0;
+}
+
+.settings-subtab {
+  display: block;
+  width: 100%;
+  padding: 10px 20px;
+  background: none;
+  border: none;
+  border-left: 2px solid transparent;
+  color: var(--text-secondary);
+  cursor: pointer;
+  font-size: 14px;
+  font-weight: 500;
+  text-align: left;
+  transition: color 0.2s, background 0.2s, border-color 0.2s;
+}
+
+.settings-subtab:hover {
+  color: var(--text);
+  background: var(--bg-tertiary);
+}
+
+.settings-subtab.active {
+  color: var(--accent);
+  border-left-color: var(--accent);
+  background: var(--bg-tertiary);
+}
+
+.settings-content {
+  flex: 1;
+  overflow: hidden;
+  display: flex;
+  flex-direction: column;
+}
+
+.settings-subpanel {
+  display: none;
+  flex: 1;
+  overflow: hidden;
+  flex-direction: column;
+  opacity: 0;
+}
+
+.settings-subpanel.active {
+  display: flex;
+  animation: settingsFadeIn 0.2s ease forwards;
+}
+
+@keyframes settingsFadeIn {
+  from { opacity: 0; transform: translateY(6px); }
+  to { opacity: 1; transform: translateY(0); }
+}
+
+/* Settings form styles (General subtab) */
+.settings-group {
+  background: var(--bg-secondary);
+  border: 1px solid var(--border);
+  border-radius: var(--radius-lg);
+  padding: 16px;
+  margin-bottom: 16px;
+}
+
+.settings-group-title {
+  font-size: 11px;
+  font-weight: 600;
+  color: var(--text-secondary);
+  margin-bottom: 12px;
+  text-transform: uppercase;
+  letter-spacing: 0.05em;
+  padding-bottom: 8px;
+  border-bottom: 1px solid var(--border);
+}
+
+.settings-row {
+  display: flex;
+  align-items: center;
+  justify-content: space-between;
+  padding: 10px 12px;
+  margin: 0 -12px;
+  border-bottom: 1px solid rgba(255,255,255,0.04);
+  border-radius: 6px;
+  gap: 16px;
+  max-height: 80px;
+  overflow: hidden;
+  transition: max-height 0.2s ease, opacity 0.2s ease, margin 0.2s ease, padding 0.2s ease, background var(--transition-fast);
+  opacity: 1;
+}
+
+.settings-row:hover {
+  background: var(--bg-hover);
+}
+
+.settings-row.hidden {
+  max-height: 0;
+  opacity: 0;
+  margin: 0;
+  padding: 0;
+  border-bottom: none;
+}
+
+.settings-row.search-hidden {
+  display: none;
+}
+
+.settings-row:last-child { border-bottom: none; }
+
+.settings-label {
+  font-size: 13px;
+  color: var(--text);
+  font-weight: 500;
+  flex-shrink: 0;
+  min-width: 180px;
+}
+
+.settings-input {
+  padding: 6px 10px;
+  background: var(--bg);
+  border: 1px solid var(--border);
+  border-radius: var(--radius);
+  color: var(--text);
+  font-size: 13px;
+  font-family: 'IBM Plex Mono', monospace;
+  width: 240px;
+  max-width: 100%;
+}
+
+.settings-input:focus {
+  outline: none;
+  border-color: var(--accent);
+  box-shadow: 0 0 0 3px rgba(52, 211, 153, 0.15);
+}
+
+.settings-saved-indicator {
+  font-size: 11px;
+  color: var(--success);
+  opacity: 0;
+  transform: translateY(4px);
+  transition: opacity 0.3s ease, transform 0.3s ease;
+}
+
+.settings-saved-indicator.visible {
+  opacity: 1;
+  transform: translateY(0);
+}
+
+.settings-description {
+  font-size: 11px;
+  color: var(--text-secondary);
+  margin-top: 2px;
+}
+
+.restart-banner {
+  display: flex;
+  align-items: center;
+  gap: 10px;
+  padding: 10px 14px;
+  background: var(--warning-soft);
+  border: 1px solid rgba(245, 166, 35, 0.25);
+  border-radius: var(--radius);
+  color: var(--text);
+  font-size: 12px;
+  margin: 8px 16px;
+  animation: settingsFadeIn 0.25s ease forwards;
+}
+
+.restart-banner-text {
+  flex: 1;
+}
+
+.restart-banner-btn {
+  padding: 4px 12px;
+  background: var(--warning);
+  color: #09090b;
+  border: none;
+  border-radius: var(--radius);
+  cursor: pointer;
+  font-size: 11px;
+  font-weight: 600;
+  white-space: nowrap;
+  transition: opacity var(--transition-fast);
+}
+
+.restart-banner-btn:hover {
+  opacity: 0.85;
+}
+
+.settings-label-wrap {
+  display: flex;
+  flex-direction: column;
+  flex-shrink: 0;
+  min-width: 180px;
+}
+
+.settings-select {
+  padding: 6px 10px;
+  background: var(--bg);
+  border: 1px solid var(--border);
+  border-radius: var(--radius);
+  color: var(--text);
+  font-size: 13px;
+  font-family: 'IBM Plex Mono', monospace;
+  width: 240px;
+  max-width: 100%;
+  cursor: pointer;
+}
+
+.settings-select:focus {
+  outline: none;
+  border-color: var(--accent);
+  box-shadow: 0 0 0 3px rgba(52, 211, 153, 0.15);
+}
+
+input[type="checkbox"]:focus-visible {
+  outline: 2px solid var(--accent);
+  outline-offset: 2px;
+}
+
 /* Slash command autocomplete dropdown */
 .slash-autocomplete {
  position: relative;
@@ -4078,3 +4432,211 @@ mark {
  padding: 4px 8px;
  background: var(--bg-secondary);
 }
+
+/* Settings toolbar (search + import/export) */
+.settings-toolbar {
+  display: flex;
+  align-items: center;
+  gap: 8px;
+  padding: 8px 16px;
+  border-bottom: 1px solid var(--border);
+  background: var(--bg-secondary);
+  flex-shrink: 0;
+}
+
+.settings-search {
+  flex: 1;
+}
+
+.settings-search input {
+  width: 100%;
+  padding: 6px 10px 6px 32px;
+  background: var(--bg);
+  background-image: url("data:image/svg+xml,%3Csvg xmlns='http://www.w3.org/2000/svg' width='14' height='14' viewBox='0 0 24 24' fill='none' stroke='%2371717a' stroke-width='2' stroke-linecap='round' stroke-linejoin='round'%3E%3Ccircle cx='11' cy='11' r='8'/%3E%3Cpath d='M21 21l-4.35-4.35'/%3E%3C/svg%3E");
+  background-repeat: no-repeat;
+  background-position: 10px center;
+  border: 1px solid var(--border);
+  border-radius: var(--radius);
+  color: var(--text);
+  font-size: 13px;
+  font-family: 'IBM Plex Mono', monospace;
+}
+
+.settings-search input:focus {
+  outline: none;
+  border-color: var(--accent);
+  box-shadow: 0 0 0 3px rgba(52, 211, 153, 0.15);
+}
+
+.settings-toolbar-btn {
+  padding: 6px 12px;
+  background: var(--bg-tertiary);
+  border: 1px solid var(--border);
+  border-radius: var(--radius);
+  color: var(--text-secondary);
+  font-size: 12px;
+  font-weight: 500;
+  cursor: pointer;
+  transition: all var(--transition-fast);
+  white-space: nowrap;
+}
+
+.settings-toolbar-btn:hover {
+  background: var(--bg-secondary);
+  color: var(--text);
+  border-color: rgba(255, 255, 255, 0.15);
+  transform: translateY(-1px);
+}
+
+.settings-toolbar-btn:active {
+  transform: scale(0.98);
+}
+
+/* Confirmation modal */
+.modal-overlay {
+  position: fixed;
+  top: 0;
+  left: 0;
+  right: 0;
+  bottom: 0;
+  background: rgba(0, 0, 0, 0.6);
+  backdrop-filter: blur(4px);
+  display: flex;
+  align-items: center;
+  justify-content: center;
+  z-index: 1000;
+  animation: modalFadeIn 0.15s ease;
+}
+
+@keyframes modalFadeIn {
+  from { opacity: 0; }
+  to { opacity: 1; }
+}
+
+@keyframes modalSlideIn {
+  from { opacity: 0; transform: translateY(10px) scale(0.98); }
+  to { opacity: 1; transform: translateY(0) scale(1); }
+}
+
+.modal {
+  background: var(--bg-secondary);
+  border: 1px solid var(--border);
+  border-radius: var(--radius-lg);
+  padding: 0;
+  max-width: 420px;
+  width: 90%;
+  box-shadow: 0 25px 50px -12px rgba(0, 0, 0, 0.5);
+  animation: modalSlideIn 0.2s ease;
+}
+
+.modal h3 {
+  margin: 0;
+  padding: 16px 20px;
+  font-size: 16px;
+  color: var(--text);
+  border-bottom: 1px solid var(--border);
+}
+
+.modal p {
+  margin: 0;
+  padding: 16px 20px;
+  font-size: 13px;
+  color: var(--text-secondary);
+}
+
+.modal-actions {
+  display: flex;
+  justify-content: flex-end;
+  gap: 8px;
+  padding: 12px 20px;
+  border-top: 1px solid var(--border);
+}
+
+.btn-secondary {
+  padding: 8px 16px;
+  background: var(--bg-tertiary);
+  border: 1px solid var(--border);
+  border-radius: var(--radius);
+  color: var(--text);
+  cursor: pointer;
+  font-size: 13px;
+}
+
+.btn-secondary:hover {
+  background: var(--bg);
+}
+
+.btn-danger {
+  padding: 8px 16px;
+  background: var(--danger);
+  border: 1px solid var(--danger);
+  border-radius: var(--radius);
+  color: white;
+  cursor: pointer;
+  font-size: 13px;
+}
+
+.btn-danger:hover {
+  opacity: 0.9;
+}
+
+/* Mobile settings responsiveness */
+@media (max-width: 768px) {
+  .settings-row {
+    flex-direction: column;
+    align-items: stretch;
+    max-height: 140px;
+  }
+  .settings-label-wrap {
+    min-width: unset;
+  }
+  .settings-input, .settings-select {
+    width: 100%;
+  }
+  .settings-toolbar {
+    flex-wrap: wrap;
+  }
+  .settings-search {
+    min-width: 150px;
+  }
+}
+
+/* Loading skeletons */
+@keyframes shimmer {
+  0% { background-position: -200% 0; }
+  100% { background-position: 200% 0; }
+}
+
+.skeleton-row {
+  display: flex;
+  align-items: center;
+  justify-content: space-between;
+  padding: 10px 12px;
+  gap: 16px;
+}
+
+.skeleton-bar {
+  height: 12px;
+  border-radius: 6px;
+  background: linear-gradient(90deg, var(--bg-tertiary) 25%, rgba(255,255,255,0.06) 50%, var(--bg-tertiary) 75%);
+  background-size: 200% 100%;
+  animation: shimmer 1.5s ease-in-out infinite;
+}
+
+.skeleton-card {
+  background: var(--bg-secondary);
+  border: 1px solid var(--border);
+  border-radius: var(--radius-lg);
+  padding: 14px;
+  display: flex;
+  flex-direction: column;
+  gap: 10px;
+}
+
+/* Settings search empty state */
+.settings-search-empty {
+  padding: 32px 16px;
+  text-align: center;
+  color: var(--text-muted);
+  font-size: 13px;
+}
@@ -87,6 +87,7 @@ impl TestGatewayBuilder {
            cost_guard: None,
            routine_engine: Arc::new(tokio::sync::RwLock::new(None)),
            startup_time: std::time::Instant::now(),
+            active_config: crate::channels::web::server::ActiveConfigSnapshot::default(),
        })
    }

@@ -116,9 +116,153 @@ pub struct ApprovalRequest {

 // --- SSE Event Types ---

-/// Re-export from `crate::events::DomainEvent` — the canonical event enum now
-/// lives in a channel-neutral location so agent code doesn't depend on `channels::web`.
-pub use crate::events::DomainEvent as SseEvent;
+#[derive(Debug, Clone, Serialize)]
+#[serde(tag = "type")]
+pub enum SseEvent {
+    #[serde(rename = "response")]
+    Response { content: String, thread_id: String },
+    #[serde(rename = "thinking")]
+    Thinking {
+        message: String,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        thread_id: Option<String>,
+    },
+    #[serde(rename = "tool_started")]
+    ToolStarted {
+        name: String,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        thread_id: Option<String>,
+    },
+    #[serde(rename = "tool_completed")]
+    ToolCompleted {
+        name: String,
+        success: bool,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        error: Option<String>,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        parameters: Option<String>,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        thread_id: Option<String>,
+    },
+    #[serde(rename = "tool_result")]
+    ToolResult {
+        name: String,
+        preview: String,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        thread_id: Option<String>,
+    },
+    #[serde(rename = "stream_chunk")]
+    StreamChunk {
+        content: String,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        thread_id: Option<String>,
+    },
+    #[serde(rename = "status")]
+    Status {
+        message: String,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        thread_id: Option<String>,
+    },
+    #[serde(rename = "job_started")]
+    JobStarted {
+        job_id: String,
+        title: String,
+        browse_url: String,
+    },
+    #[serde(rename = "approval_needed")]
+    ApprovalNeeded {
+        request_id: String,
+        tool_name: String,
+        description: String,
+        parameters: String,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        thread_id: Option<String>,
+        /// Whether the "always" auto-approve option should be shown.
+        allow_always: bool,
+    },
+    #[serde(rename = "auth_required")]
+    AuthRequired {
+        extension_name: String,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        instructions: Option<String>,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        auth_url: Option<String>,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        setup_url: Option<String>,
+    },
+    #[serde(rename = "auth_completed")]
+    AuthCompleted {
+        extension_name: String,
+        success: bool,
+        message: String,
+    },
+    #[serde(rename = "error")]
+    Error {
+        message: String,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        thread_id: Option<String>,
+    },
+    #[serde(rename = "heartbeat")]
+    Heartbeat,
+
+    // Sandbox job streaming events (worker + Claude Code bridge)
+    #[serde(rename = "job_message")]
+    JobMessage {
+        job_id: String,
+        role: String,
+        content: String,
+    },
+    #[serde(rename = "job_tool_use")]
+    JobToolUse {
+        job_id: String,
+        tool_name: String,
+        input: serde_json::Value,
+    },
+    #[serde(rename = "job_tool_result")]
+    JobToolResult {
+        job_id: String,
+        tool_name: String,
+        output: String,
+    },
+    #[serde(rename = "job_status")]
+    JobStatus { job_id: String, message: String },
+    #[serde(rename = "job_result")]
+    JobResult {
+        job_id: String,
+        status: String,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        session_id: Option<String>,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        fallback_deliverable: Option<serde_json::Value>,
+    },
+
+    /// An image was generated by a tool.
+    #[serde(rename = "image_generated")]
+    ImageGenerated {
+        data_url: String,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        path: Option<String>,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        thread_id: Option<String>,
+    },
+
+    /// Suggested follow-up messages for the user.
+    #[serde(rename = "suggestions")]
+    Suggestions {
+        suggestions: Vec<String>,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        thread_id: Option<String>,
+    },
+
+    /// Extension activation status change (WASM channels).
+    #[serde(rename = "extension_status")]
+    ExtensionStatus {
+        extension_name: String,
+        status: String,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        message: Option<String>,
+    },
+}

 // --- Memory ---

@@ -270,6 +414,40 @@ pub struct TransitionInfo {

 // --- Extensions ---

+#[derive(Debug, Clone, Copy, PartialEq, Eq, Serialize)]
+#[serde(rename_all = "snake_case")]
+pub enum ExtensionActivationStatus {
+    Installed,
+    Configured,
+    Pairing,
+    Active,
+    Failed,
+}
+
+pub fn classify_wasm_channel_activation(
+    ext: &crate::extensions::InstalledExtension,
+    has_paired: bool,
+    has_owner_binding: bool,
+) -> Option<ExtensionActivationStatus> {
+    if ext.kind != crate::extensions::ExtensionKind::WasmChannel {
+        return None;
+    }
+
+    Some(if ext.activation_error.is_some() {
+        ExtensionActivationStatus::Failed
+    } else if !ext.authenticated {
+        ExtensionActivationStatus::Installed
+    } else if ext.active {
+        if has_paired || has_owner_binding {
+            ExtensionActivationStatus::Active
+        } else {
+            ExtensionActivationStatus::Pairing
+        }
+    } else {
+        ExtensionActivationStatus::Configured
+    })
+}
+
 #[derive(Debug, Serialize)]
 pub struct ExtensionInfo {
    pub name: String,
@@ -288,9 +466,9 @@ pub struct ExtensionInfo {
    /// Whether this extension has an auth configuration (OAuth or manual token).
    #[serde(default)]
    pub has_auth: bool,
-    /// WASM channel activation status: "installed", "configured", "active", "failed".
+    /// WASM channel activation status.
    #[serde(skip_serializing_if = "Option::is_none")]
-    pub activation_status: Option<String>,
+    pub activation_status: Option<ExtensionActivationStatus>,
    /// Human-readable error when activation_status is "failed".
    #[serde(skip_serializing_if = "Option::is_none")]
    pub activation_error: Option<String>,
@@ -363,6 +541,9 @@ pub struct ActionResponse {
    /// Whether the channel was successfully activated after setup.
    #[serde(skip_serializing_if = "Option::is_none")]
    pub activated: Option<bool>,
+    /// Pending manual verification challenge (for Telegram owner binding, etc.).
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub verification: Option<crate::extensions::VerificationChallenge>,
 }

 impl ActionResponse {
@@ -374,6 +555,7 @@ impl ActionResponse {
            awaiting_token: None,
            instructions: None,
            activated: None,
+            verification: None,
        }
    }

@@ -385,6 +567,7 @@ impl ActionResponse {
            awaiting_token: None,
            instructions: None,
            activated: None,
+            verification: None,
        }
    }
 }
@@ -901,6 +1084,7 @@ mod tests {
            description: "Run ls".to_string(),
            parameters: "{}".to_string(),
            thread_id: Some("t1".to_string()),
+            allow_always: true,
        };
        let ws = WsServerMessage::from_sse_event(&sse);
        match ws {
@@ -2,10 +2,28 @@

 use crate::channels::web::types::{ToolCallInfo, TurnInfo};

-/// Delegates to [`crate::util::truncate_preview`] — the canonical implementation
-/// now lives in the shared utility module so non-web code can use it too.
+/// Truncate a string to at most `max_bytes` bytes at a char boundary, appending "...".
+///
+/// If the input is wrapped in `<tool_output …>…</tool_output>` and truncation
+/// removes the closing tag, the tag is re-appended so downstream XML parsers
+/// never see an unclosed element.
 pub fn truncate_preview(s: &str, max_bytes: usize) -> String {
-    crate::util::truncate_preview(s, max_bytes)
+    if s.len() <= max_bytes {
+        return s.to_string();
+    }
+    // Walk backwards from max_bytes to find a valid char boundary
+    let mut end = max_bytes;
+    while end > 0 && !s.is_char_boundary(end) {
+        end -= 1;
+    }
+    let mut result = format!("{}...", &s[..end]);
+
+    // Re-close <tool_output> if truncation cut through the closing tag.
+    if s.starts_with("<tool_output") && !result.ends_with("</tool_output>") {
+        result.push_str("\n</tool_output>");
+    }
+
+    result
 }

 /// Build TurnInfo pairs from flat DB messages (user/tool_calls/assistant triples).
@@ -265,14 +265,25 @@ async fn handle_client_message(
            if let Some(ref ext_mgr) = state.extension_manager {
                match ext_mgr.configure_token(&extension_name, &token).await {
                    Ok(result) => {
-                        crate::channels::web::server::clear_auth_mode(state).await;
-                        state
-                            .sse
-                            .broadcast(crate::channels::web::types::SseEvent::AuthCompleted {
-                                extension_name,
-                                success: true,
-                                message: result.message,
-                            });
+                        if result.verification.is_some() {
+                            state.sse.broadcast(
+                                crate::channels::web::types::SseEvent::AuthRequired {
+                                    extension_name: extension_name.clone(),
+                                    instructions: Some(result.message),
+                                    auth_url: None,
+                                    setup_url: None,
+                                },
+                            );
+                        } else {
+                            crate::channels::web::server::clear_auth_mode(state).await;
+                            state.sse.broadcast(
+                                crate::channels::web::types::SseEvent::AuthCompleted {
+                                    extension_name,
+                                    success: true,
+                                    message: result.message,
+                                },
+                            );
+                        }
                    }
                    Err(e) => {
                        let msg = format!("Auth failed: {}", e);
@@ -510,6 +521,7 @@ mod tests {
            cost_guard: None,
            routine_engine: Arc::new(tokio::sync::RwLock::new(None)),
            startup_time: std::time::Instant::now(),
+            active_config: crate::channels::web::server::ActiveConfigSnapshot::default(),
        }
    }
 }
@@ -33,7 +33,7 @@ pub async fn run_doctor_command() -> anyhow::Result<()> {

    check(
        "NEAR AI session",
-        check_nearai_session().await,
+        check_nearai_session(&settings).await,
        &mut passed,
        &mut failed,
        &mut skipped,
@@ -215,7 +215,22 @@ fn check_settings_file() -> CheckResult {

 // ── NEAR AI session ─────────────────────────────────────────

-async fn check_nearai_session() -> CheckResult {
+async fn check_nearai_session(settings: &Settings) -> CheckResult {
+    // Skip entirely when the configured backend is not NEAR AI.
+    let llm_config = match crate::config::LlmConfig::resolve(settings) {
+        Ok(config) => config,
+        Err(e) => {
+            // check_llm_config will report the full error; just skip here.
+            return CheckResult::Skip(format!("LLM config error: {e}"));
+        }
+    };
+    if llm_config.backend != "nearai" {
+        return CheckResult::Skip(format!(
+            "not using NEAR AI backend (backend={})",
+            llm_config.backend
+        ));
+    }
+
    // Check if session file exists
    let session_path = crate::config::llm::default_session_path();
    if !session_path.exists() {
@@ -405,10 +420,11 @@ fn check_routines_config() -> CheckResult {
 fn check_gateway_config(settings: &Settings) -> CheckResult {
    // Use the same resolve() path as runtime so invalid env values
    // (e.g. GATEWAY_PORT=abc) are caught here too.
-    let tunnel_enabled = crate::config::TunnelConfig::resolve(settings)
-        .map(|t| t.is_enabled())
-        .unwrap_or(false);
-    match crate::config::ChannelsConfig::resolve(settings, tunnel_enabled) {
+    let owner_id = match crate::config::resolve_owner_id(settings) {
+        Ok(owner_id) => owner_id,
+        Err(e) => return CheckResult::Fail(format!("config error: {e}")),
+    };
+    match crate::config::ChannelsConfig::resolve(settings, &owner_id) {
        Ok(channels) => match channels.gateway {
            Some(gw) => {
                if gw.auth_token.is_some() {
@@ -619,12 +635,53 @@ mod tests {

    #[tokio::test]
    async fn check_nearai_session_does_not_panic() {
-        let result = check_nearai_session().await;
+        let settings = Settings::default();
+        let result = check_nearai_session(&settings).await;
        match result {
            CheckResult::Pass(_) | CheckResult::Fail(_) | CheckResult::Skip(_) => {}
        }
    }

+    #[test]
+    fn check_nearai_session_skips_for_non_nearai_backend() {
+        struct EnvGuard(&'static str, Option<String>);
+        impl Drop for EnvGuard {
+            fn drop(&mut self) {
+                // SAFETY: Under ENV_MUTEX.
+                unsafe {
+                    match &self.1 {
+                        Some(val) => std::env::set_var(self.0, val),
+                        None => std::env::remove_var(self.0),
+                    }
+                }
+            }
+        }
+
+        let _mutex = crate::config::helpers::ENV_MUTEX.lock().expect("env mutex");
+        let prev = std::env::var("LLM_BACKEND").ok();
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe {
+            std::env::set_var("LLM_BACKEND", "anthropic");
+        }
+        let _env_guard = EnvGuard("LLM_BACKEND", prev);
+
+        let settings = Settings::default();
+        let rt = tokio::runtime::Runtime::new().expect("tokio runtime");
+        let result = rt.block_on(check_nearai_session(&settings));
+        match result {
+            CheckResult::Skip(msg) => {
+                assert!(
+                    msg.contains("backend=anthropic"),
+                    "expected backend name in skip message, got: {msg}"
+                );
+            }
+            other => panic!(
+                "expected Skip for non-nearai backend, got: {}",
+                format_result(&other)
+            ),
+        }
+    }
+
    #[test]
    fn check_settings_file_handles_missing() {
        // Settings::default_path() might or might not exist, but must not panic
@@ -223,8 +223,8 @@ async fn cmd_follow(cmd: &LogsCommand, params: &GatewayParams) -> anyhow::Result

        // Process complete lines from the buffer.
        while let Some(newline_pos) = buffer.find('\n') {
-            let line = buffer[..newline_pos].to_string(); // safety: find('\n') returns char boundary
-            buffer = buffer[newline_pos + 1..].to_string(); // safety: '\n' is single byte
+            let line = buffer[..newline_pos].to_string();
+            buffer = buffer[newline_pos + 1..].to_string();

            // SSE format: "data: {...}" lines carry the payload.
            if let Some(data) = line.strip_prefix("data: ")
@@ -487,25 +487,25 @@ mod tests {

    #[test]
    fn test_colorize_level() {
-        assert!(colorize_level("ERROR").contains("\x1b[31m")); // safety: test-only
-        assert!(colorize_level("WARN").contains("\x1b[33m")); // safety: test-only
-        assert!(colorize_level("INFO").contains("\x1b[32m")); // safety: test-only
-        assert!(colorize_level("DEBUG").contains("\x1b[36m")); // safety: test-only
-        assert!(colorize_level("TRACE").contains("\x1b[90m")); // safety: test-only
-        assert_eq!(colorize_level("UNKNOWN"), "UNKNOWN"); // safety: test-only
+        assert!(colorize_level("ERROR").contains("\x1b[31m"));
+        assert!(colorize_level("WARN").contains("\x1b[33m"));
+        assert!(colorize_level("INFO").contains("\x1b[32m"));
+        assert!(colorize_level("DEBUG").contains("\x1b[36m"));
+        assert!(colorize_level("TRACE").contains("\x1b[90m"));
+        assert_eq!(colorize_level("UNKNOWN"), "UNKNOWN");
    }

    #[test]
    fn test_convert_to_local_time_valid() {
        let ts = "2024-01-15T10:30:00.000Z";
        let result = convert_to_local_time(ts);
-        assert!(result.contains("2024-01-15")); // safety: test-only
+        assert!(result.contains("2024-01-15"));
    }

    #[test]
    fn test_convert_to_local_time_invalid() {
        let ts = "not-a-timestamp";
-        assert_eq!(convert_to_local_time(ts), "not-a-timestamp"); // safety: test-only
+        assert_eq!(convert_to_local_time(ts), "not-a-timestamp");
    }

    #[test]
@@ -533,55 +533,55 @@ mod tests {

    #[test]
    fn test_tail_file_small() {
-        let dir = tempfile::tempdir().unwrap(); // safety: test-only
+        let dir = tempfile::tempdir().unwrap();
        let path = dir.path().join("test.log");
-        std::fs::write(&path, "line1\nline2\nline3\nline4\nline5\n").unwrap(); // safety: test-only
+        std::fs::write(&path, "line1\nline2\nline3\nline4\nline5\n").unwrap();

-        let result = tail_file(&path, 3).unwrap(); // safety: test-only
-        assert_eq!(result, vec!["line3", "line4", "line5"]); // safety: test-only
+        let result = tail_file(&path, 3).unwrap();
+        assert_eq!(result, vec!["line3", "line4", "line5"]);
    }

    #[test]
    fn test_tail_file_fewer_lines_than_limit() {
-        let dir = tempfile::tempdir().unwrap(); // safety: test-only
+        let dir = tempfile::tempdir().unwrap();
        let path = dir.path().join("test.log");
-        std::fs::write(&path, "a\nb\n").unwrap(); // safety: test-only
+        std::fs::write(&path, "a\nb\n").unwrap();

-        let result = tail_file(&path, 200).unwrap(); // safety: test-only
-        assert_eq!(result, vec!["a", "b"]); // safety: test-only
+        let result = tail_file(&path, 200).unwrap();
+        assert_eq!(result, vec!["a", "b"]);
    }

    #[test]
    fn test_tail_file_empty() {
-        let dir = tempfile::tempdir().unwrap(); // safety: test-only
+        let dir = tempfile::tempdir().unwrap();
        let path = dir.path().join("test.log");
-        std::fs::write(&path, "").unwrap(); // safety: test-only
+        std::fs::write(&path, "").unwrap();

-        let result = tail_file(&path, 10).unwrap(); // safety: test-only
-        assert!(result.is_empty()); // safety: test-only
+        let result = tail_file(&path, 10).unwrap();
+        assert!(result.is_empty());
    }

    #[test]
    fn test_tail_file_large() {
-        let dir = tempfile::tempdir().unwrap(); // safety: test-only
+        let dir = tempfile::tempdir().unwrap();
        let path = dir.path().join("big.log");
        // Write 10000 lines to test chunked reading.
        let content: String = (0..10000).map(|i| format!("line {}\n", i)).collect();
-        std::fs::write(&path, &content).unwrap(); // safety: test-only
+        std::fs::write(&path, &content).unwrap();

-        let result = tail_file(&path, 5).unwrap(); // safety: test-only
-        assert_eq!(result.len(), 5); // safety: test-only
-        assert_eq!(result[0], "line 9995"); // safety: test-only
-        assert_eq!(result[4], "line 9999"); // safety: test-only
+        let result = tail_file(&path, 5).unwrap();
+        assert_eq!(result.len(), 5);
+        assert_eq!(result[0], "line 9995");
+        assert_eq!(result[4], "line 9999");
    }

    #[test]
    fn test_tail_file_no_trailing_newline() {
-        let dir = tempfile::tempdir().unwrap(); // safety: test-only
+        let dir = tempfile::tempdir().unwrap();
        let path = dir.path().join("test.log");
-        std::fs::write(&path, "line1\nline2\nline3").unwrap(); // safety: test-only
+        std::fs::write(&path, "line1\nline2\nline3").unwrap();

-        let result = tail_file(&path, 2).unwrap(); // safety: test-only
-        assert_eq!(result, vec!["line2", "line3"]); // safety: test-only
+        let result = tail_file(&path, 2).unwrap();
+        assert_eq!(result, vec!["line2", "line3"]);
    }
 }
@@ -7,17 +7,18 @@ use std::sync::Arc;

 use clap::Subcommand;

-use crate::workspace::{EmbeddingProvider, SearchConfig, Workspace};
+use crate::workspace::{EmbeddingCacheConfig, EmbeddingProvider, SearchConfig, Workspace};

 /// Run a memory command using the Database trait (works with any backend).
 pub async fn run_memory_command_with_db(
    cmd: MemoryCommand,
    db: std::sync::Arc<dyn crate::db::Database>,
    embeddings: Option<Arc<dyn EmbeddingProvider>>,
+    cache_config: EmbeddingCacheConfig,
 ) -> anyhow::Result<()> {
    let mut workspace = Workspace::new_with_db("default", db);
    if let Some(emb) = embeddings {
-        workspace = workspace.with_embeddings(emb);
+        workspace = workspace.with_embeddings_cached(emb, cache_config);
    }

    match cmd {
@@ -85,10 +86,11 @@ pub async fn run_memory_command(
    cmd: MemoryCommand,
    pool: deadpool_postgres::Pool,
    embeddings: Option<Arc<dyn EmbeddingProvider>>,
+    cache_config: EmbeddingCacheConfig,
 ) -> anyhow::Result<()> {
    let mut workspace = Workspace::new("default", pool);
    if let Some(emb) = embeddings {
-        workspace = workspace.with_embeddings(emb);
+        workspace = workspace.with_embeddings_cached(emb, cache_config);
    }

    match cmd {
@@ -336,7 +336,10 @@ pub async fn run_memory_command(mem_cmd: &MemoryCommand) -> anyhow::Result<()> {
        .await
        .map_err(|e| anyhow::anyhow!("{}", e))?;

-    run_memory_command_with_db(mem_cmd.clone(), db, embeddings).await
+    let cache_config = crate::workspace::EmbeddingCacheConfig {
+        max_entries: config.embeddings.cache_size,
+    };
+    run_memory_command_with_db(mem_cmd.clone(), db, embeddings, cache_config).await
 }

 #[cfg(test)]
@@ -5,17 +5,10 @@
 //!
 //! # Built-in Credentials
 //!
-//! Many CLI tools (gcloud, rclone, gdrive) ship with default OAuth credentials
-//! so users don't need to register their own OAuth app. Google explicitly
-//! documents that client_secret for "Desktop App" / "Installed App" types
-//! is NOT actually secret.
-//!
-//! Default credentials are hardcoded below. They can be overridden at:
-//!
-//! - **Compile time**: Set IRONCLAW_GOOGLE_CLIENT_ID / IRONCLAW_GOOGLE_CLIENT_SECRET
-//!   env vars before building to replace the hardcoded defaults.
-//! - **Runtime**: Users can set GOOGLE_OAUTH_CLIENT_ID / GOOGLE_OAUTH_CLIENT_SECRET
-//!   env vars, which take priority over built-in defaults.
+//! Some providers ship with built-in OAuth credentials so users don't need to
+//! register their own OAuth app just to get started. Today this module only
+//! includes built-in defaults for Google-family tools, and those defaults can
+//! be overridden by provider-specific environment variables when needed.

 use std::collections::HashMap;
 use std::sync::Arc;
@@ -23,6 +16,7 @@ use std::time::Duration;

 use base64::{Engine, engine::general_purpose::URL_SAFE_NO_PAD};
 use rand::RngCore;
+use serde::{Deserialize, Serialize};
 use sha2::{Digest, Sha256};
 use tokio::sync::RwLock;

@@ -60,6 +54,14 @@ pub fn builtin_credentials(secret_name: &str) -> Option<OAuthCredentials> {
    }
 }

+/// Returns the compile-time override env var name, if this provider supports one.
+pub fn builtin_client_id_override_env(secret_name: &str) -> Option<&'static str> {
+    match secret_name {
+        "google_oauth_token" => Some("IRONCLAW_GOOGLE_CLIENT_ID"),
+        _ => None,
+    }
+}
+
 // ── Shared callback server ──────────────────────────────────────────────

 // Core OAuth callback infrastructure is defined in `crate::llm::oauth_helpers`
@@ -173,9 +175,8 @@ pub async fn exchange_oauth_code(
    code_verifier: Option<&str>,
    access_token_field: &str,
 ) -> Result<OAuthTokenResponse, OAuthCallbackError> {
-    // Delegates to exchange_oauth_code_with_resource with resource=None.
-    // Non-MCP OAuth flows don't need the RFC 8707 resource parameter.
-    exchange_oauth_code_with_resource(
+    let extra_token_params = HashMap::new();
+    exchange_oauth_code_with_params(
        token_url,
        client_id,
        client_secret,
@@ -183,16 +184,14 @@ pub async fn exchange_oauth_code(
        redirect_uri,
        code_verifier,
        access_token_field,
-        None,
+        &extra_token_params,
    )
    .await
 }

-/// Exchange an OAuth authorization code for tokens, with optional RFC 8707 `resource` parameter.
-///
-/// The `resource` parameter scopes the issued token to a specific server (used by MCP OAuth).
+/// Exchange an OAuth authorization code for tokens with generic extra form parameters.
 #[allow(clippy::too_many_arguments)]
-pub async fn exchange_oauth_code_with_resource(
+pub async fn exchange_oauth_code_with_params(
    token_url: &str,
    client_id: &str,
    client_secret: Option<&str>,
@@ -200,7 +199,7 @@ pub async fn exchange_oauth_code_with_resource(
    redirect_uri: &str,
    code_verifier: Option<&str>,
    access_token_field: &str,
-    resource: Option<&str>,
+    extra_token_params: &HashMap<String, String>,
 ) -> Result<OAuthTokenResponse, OAuthCallbackError> {
    let client = reqwest::Client::new();
    let mut token_params = vec![
@@ -213,10 +212,8 @@ pub async fn exchange_oauth_code_with_resource(
        token_params.push(("code_verifier", verifier.to_string()));
    }

-    // RFC 8707: include the `resource` parameter so the authorization server
-    // scopes the issued token to the specific MCP server (protected resource).
-    if let Some(resource) = resource {
-        token_params.push(("resource", resource.to_string()));
+    for (key, value) in extra_token_params {
+        token_params.push((key.as_str(), value.clone()));
    }

    let mut request = client.post(token_url);
@@ -276,6 +273,37 @@ pub async fn exchange_oauth_code_with_resource(
    })
 }

+/// Exchange an OAuth authorization code for tokens, with optional RFC 8707 `resource` parameter.
+///
+/// The `resource` parameter scopes the issued token to a specific server (used by MCP OAuth).
+#[allow(clippy::too_many_arguments)]
+pub async fn exchange_oauth_code_with_resource(
+    token_url: &str,
+    client_id: &str,
+    client_secret: Option<&str>,
+    code: &str,
+    redirect_uri: &str,
+    code_verifier: Option<&str>,
+    access_token_field: &str,
+    resource: Option<&str>,
+) -> Result<OAuthTokenResponse, OAuthCallbackError> {
+    let mut extra_token_params = HashMap::new();
+    if let Some(resource) = resource {
+        extra_token_params.insert("resource".to_string(), resource.to_string());
+    }
+    exchange_oauth_code_with_params(
+        token_url,
+        client_id,
+        client_secret,
+        code,
+        redirect_uri,
+        code_verifier,
+        access_token_field,
+        &extra_token_params,
+    )
+    .await
+}
+
 /// Store OAuth tokens (access + refresh) in the secrets store.
 ///
 /// Also stores the granted scopes as `{secret_name}_scopes` so that scope
@@ -423,9 +451,9 @@ pub struct PendingOAuthFlow {
    pub sse_sender: Option<tokio::sync::broadcast::Sender<crate::channels::web::types::SseEvent>>,
    /// Gateway auth token for authenticating with the platform token exchange proxy.
    pub gateway_token: Option<String>,
-    /// RFC 8707 resource parameter (MCP OAuth only).
-    /// Sent during token exchange to scope the token to a specific MCP server.
-    pub resource: Option<String>,
+    /// Additional form params for the token exchange request.
+    /// Used for provider-specific requirements such as RFC 8707 `resource`.
+    pub token_exchange_extra_params: HashMap<String, String>,
    /// Secret name for persisting the client ID (MCP OAuth only).
    /// Needed so token refresh can find the client_id after the session ends.
    pub client_id_secret_name: Option<String>,
@@ -459,9 +487,7 @@ pub fn new_pending_oauth_registry() -> PendingOAuthRegistry {
 /// URL, meaning the user's browser will redirect to a hosted gateway rather than
 /// localhost.
 pub fn use_gateway_callback() -> bool {
-    std::env::var("IRONCLAW_OAUTH_CALLBACK_URL")
-        .ok()
-        .filter(|v| !v.is_empty())
+    crate::config::helpers::env_or_override("IRONCLAW_OAUTH_CALLBACK_URL")
        .map(|raw| {
            url::Url::parse(&raw)
                .ok()
@@ -472,6 +498,13 @@ pub fn use_gateway_callback() -> bool {
        .unwrap_or(false)
 }

+/// Returns the configured OAuth token-exchange proxy URL, if any.
+pub fn exchange_proxy_url() -> Option<String> {
+    crate::config::helpers::env_or_override("IRONCLAW_OAUTH_EXCHANGE_URL")
+        .map(|url| url.trim().to_string())
+        .filter(|url| !url.is_empty())
+}
+
 /// Maximum age for pending OAuth flows (5 minutes, matching TCP listener timeout).
 pub const OAUTH_FLOW_EXPIRY: Duration = Duration::from_secs(300);

@@ -486,23 +519,117 @@ pub async fn sweep_expired_flows(registry: &PendingOAuthRegistry) {

 // ── Platform routing helpers ────────────────────────────────────────

-/// Prepend instance name to CSRF state for platform routing.
+const HOSTED_STATE_PREFIX: &str = "ic2";
+const HOSTED_STATE_CHECKSUM_BYTES: usize = 12;
+
+#[derive(Debug, Clone, PartialEq, Eq)]
+pub struct DecodedHostedOAuthState {
+    pub flow_id: String,
+    pub instance_name: Option<String>,
+    pub is_legacy: bool,
+}
+
+#[derive(Debug, Clone, Serialize, Deserialize)]
+struct HostedOAuthStatePayload {
+    flow_id: String,
+    #[serde(default, skip_serializing_if = "Option::is_none")]
+    instance_name: Option<String>,
+    issued_at: u64,
+}
+
+fn current_instance_name() -> Option<String> {
+    crate::config::helpers::env_or_override("IRONCLAW_INSTANCE_NAME")
+        .or_else(|| crate::config::helpers::env_or_override("OPENCLAW_INSTANCE_NAME"))
+        .filter(|v| !v.is_empty())
+}
+
+fn hosted_state_checksum(payload_bytes: &[u8]) -> String {
+    let digest = Sha256::digest(payload_bytes);
+    URL_SAFE_NO_PAD.encode(&digest[..HOSTED_STATE_CHECKSUM_BYTES])
+}
+
+/// Build a versioned hosted OAuth state envelope.
 ///
-/// The NEAR AI platform nginx proxy at `auth.DOMAIN` parses the instance name
-/// from the `state` query parameter (format: `instance:nonce`) to route the
-/// OAuth callback to the correct container.
-///
-/// Returns the nonce unchanged when `IRONCLAW_INSTANCE_NAME` is not set
-/// (local/non-platform mode).
-pub fn build_platform_state(nonce: &str) -> String {
-    let instance = std::env::var("IRONCLAW_INSTANCE_NAME")
-        .or_else(|_| std::env::var("OPENCLAW_INSTANCE_NAME"))
-        .ok()
-        .filter(|v| !v.is_empty());
-    match instance {
-        Some(name) => format!("{}:{}", name, nonce),
-        None => nonce.to_string(),
+/// The encoded value is opaque to providers and can be decoded by both
+/// IronClaw and the external auth proxy for routing and callback lookup.
+pub fn encode_hosted_oauth_state(flow_id: &str, instance_name: Option<&str>) -> String {
+    let payload = HostedOAuthStatePayload {
+        flow_id: flow_id.to_string(),
+        instance_name: instance_name
+            .map(str::trim)
+            .filter(|v| !v.is_empty())
+            .map(str::to_string),
+        issued_at: std::time::SystemTime::now()
+            .duration_since(std::time::UNIX_EPOCH)
+            .unwrap_or_default()
+            .as_secs(),
+    };
+    let payload_json = match serde_json::to_vec(&payload) {
+        Ok(payload_json) => payload_json,
+        Err(error) => {
+            tracing::warn!(%error, flow_id, "Failed to serialize hosted OAuth state payload");
+            return payload.flow_id;
+        }
+    };
+    let payload = URL_SAFE_NO_PAD.encode(&payload_json);
+    let checksum = hosted_state_checksum(&payload_json);
+    format!("{HOSTED_STATE_PREFIX}.{payload}.{checksum}")
+}
+
+/// Decode hosted OAuth state in either the new versioned format or the
+/// legacy `instance:nonce`/`nonce` forms.
+pub fn decode_hosted_oauth_state(state: &str) -> Result<DecodedHostedOAuthState, String> {
+    if let Some(rest) = state.strip_prefix(&format!("{HOSTED_STATE_PREFIX}."))
+        && let Some((payload_b64, checksum)) = rest.rsplit_once('.')
+        && let Ok(payload_json) = URL_SAFE_NO_PAD.decode(payload_b64)
+    {
+        let expected_checksum = hosted_state_checksum(&payload_json);
+        if checksum != expected_checksum {
+            return Err("Hosted OAuth state checksum mismatch".to_string());
+        }
+        if let Ok(payload) = serde_json::from_slice::<HostedOAuthStatePayload>(&payload_json)
+            && !payload.flow_id.trim().is_empty()
+        {
+            return Ok(DecodedHostedOAuthState {
+                flow_id: payload.flow_id,
+                instance_name: payload.instance_name.filter(|v| !v.is_empty()),
+                is_legacy: false,
+            });
+        }
    }
+
+    if let Some((instance_name, flow_id)) = state.split_once(':') {
+        if flow_id.is_empty() {
+            return Err("Hosted OAuth legacy state is missing flow_id".to_string());
+        }
+        return Ok(DecodedHostedOAuthState {
+            flow_id: flow_id.to_string(),
+            instance_name: if instance_name.is_empty() {
+                None
+            } else {
+                Some(instance_name.to_string())
+            },
+            is_legacy: true,
+        });
+    }
+
+    if state.is_empty() {
+        return Err("Hosted OAuth state is empty".to_string());
+    }
+
+    Ok(DecodedHostedOAuthState {
+        flow_id: state.to_string(),
+        instance_name: None,
+        is_legacy: true,
+    })
+}
+
+/// Build the hosted callback state used by the public OAuth callback endpoint.
+///
+/// New flows emit a versioned opaque envelope, while callback decoding accepts
+/// both the envelope and the legacy `instance:nonce` contract.
+pub fn build_platform_state(nonce: &str) -> String {
+    encode_hosted_oauth_state(nonce, current_instance_name().as_deref())
 }

 /// Strip the instance prefix from a state parameter to recover the lookup nonce.
@@ -517,43 +644,62 @@ pub fn strip_instance_prefix(state: &str) -> &str {
        .unwrap_or(state)
 }

+pub struct ProxyTokenExchangeRequest<'a> {
+    pub proxy_url: &'a str,
+    pub gateway_token: &'a str,
+    pub token_url: &'a str,
+    pub client_id: &'a str,
+    pub client_secret: Option<&'a str>,
+    pub code: &'a str,
+    pub redirect_uri: &'a str,
+    pub code_verifier: Option<&'a str>,
+    pub access_token_field: &'a str,
+    pub extra_token_params: &'a HashMap<String, String>,
+}
+
 /// Exchange an OAuth authorization code via the platform's token exchange proxy.
 ///
-/// The proxy holds `client_secret` server-side so the container never sees it.
-/// Authenticated via the gateway auth token (Bearer header).
+/// Authenticated via the gateway auth token (Bearer header). The caller may
+/// either rely on proxy-side secret lookup or forward a `client_secret` when
+/// the provider requires it.
 ///
-/// The proxy expects form params `{code, redirect_uri, code_verifier}` and
-/// returns a standard Google token response `{access_token, refresh_token, expires_in}`.
+/// The proxy expects standard OAuth form params plus optional provider-specific
+/// token params and returns a standard token response such as
+/// `{access_token, refresh_token, expires_in}`.
 pub async fn exchange_via_proxy(
-    proxy_url: &str,
-    gateway_token: &str,
-    code: &str,
-    redirect_uri: &str,
-    code_verifier: Option<&str>,
-    access_token_field: &str,
+    request: ProxyTokenExchangeRequest<'_>,
 ) -> Result<OAuthTokenResponse, OAuthCallbackError> {
-    if gateway_token.is_empty() {
+    if request.gateway_token.is_empty() {
        return Err(OAuthCallbackError::Io(
            "Gateway auth token is required for proxy token exchange".to_string(),
        ));
    }
-    let exchange_url = format!("{}/oauth/exchange", proxy_url.trim_end_matches('/'));
+    let exchange_url = format!("{}/oauth/exchange", request.proxy_url.trim_end_matches('/'));

    let client = reqwest::Client::builder()
        .timeout(Duration::from_secs(60))
        .build()
        .map_err(|e| OAuthCallbackError::Io(format!("Failed to build HTTP client: {}", e)))?;
    let mut params = vec![
-        ("code", code.to_string()),
-        ("redirect_uri", redirect_uri.to_string()),
+        ("code", request.code.to_string()),
+        ("redirect_uri", request.redirect_uri.to_string()),
+        ("token_url", request.token_url.to_string()),
+        ("client_id", request.client_id.to_string()),
+        ("access_token_field", request.access_token_field.to_string()),
    ];
-    if let Some(verifier) = code_verifier {
+    if let Some(verifier) = request.code_verifier {
        params.push(("code_verifier", verifier.to_string()));
    }
+    if let Some(secret) = request.client_secret {
+        params.push(("client_secret", secret.to_string()));
+    }
+    for (key, value) in request.extra_token_params {
+        params.push((key.as_str(), value.clone()));
+    }

    let response = client
        .post(&exchange_url)
-        .bearer_auth(gateway_token)
+        .bearer_auth(request.gateway_token)
        .form(&params)
        .send()
        .await
@@ -576,7 +722,7 @@ pub async fn exchange_via_proxy(
        .map_err(|e| OAuthCallbackError::Io(format!("Failed to parse proxy response: {}", e)))?;

    let access_token = token_data
-        .get(access_token_field)
+        .get(request.access_token_field)
        .and_then(|v| v.as_str())
        .ok_or_else(|| {
            let fields: Vec<&str> = token_data
@@ -585,7 +731,7 @@ pub async fn exchange_via_proxy(
                .unwrap_or_default();
            OAuthCallbackError::Io(format!(
                "No '{}' field in proxy response (fields present: {:?})",
-                access_token_field, fields
+                request.access_token_field, fields
            ))
        })?
        .to_string();
@@ -605,14 +751,10 @@ pub async fn exchange_via_proxy(

 #[cfg(test)]
 mod tests {
-    use std::sync::Mutex;
-
    use crate::cli::oauth_defaults::{
        builtin_credentials, callback_host, callback_url, is_loopback_host, landing_html,
    };
-
-    /// Serializes env-mutating tests to prevent parallel races.
-    static ENV_MUTEX: Mutex<()> = Mutex::new(());
+    use crate::config::helpers::ENV_MUTEX;

    #[test]
    fn test_is_loopback_host() {
@@ -935,7 +1077,7 @@ mod tests {

    #[test]
    fn test_build_platform_state_with_instance() {
-        use crate::cli::oauth_defaults::build_platform_state;
+        use crate::cli::oauth_defaults::{build_platform_state, decode_hosted_oauth_state};

        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
        let original = std::env::var("IRONCLAW_INSTANCE_NAME").ok();
@@ -943,7 +1085,11 @@ mod tests {
        unsafe {
            std::env::set_var("IRONCLAW_INSTANCE_NAME", "kind-deer");
        }
-        assert_eq!(build_platform_state("abc123"), "kind-deer:abc123");
+        let encoded = build_platform_state("abc123");
+        let decoded = decode_hosted_oauth_state(&encoded).expect("decode hosted state");
+        assert_eq!(decoded.flow_id, "abc123");
+        assert_eq!(decoded.instance_name.as_deref(), Some("kind-deer"));
+        assert!(!decoded.is_legacy);
        unsafe {
            if let Some(val) = original {
                std::env::set_var("IRONCLAW_INSTANCE_NAME", val);
@@ -955,7 +1101,7 @@ mod tests {

    #[test]
    fn test_build_platform_state_without_instance() {
-        use crate::cli::oauth_defaults::build_platform_state;
+        use crate::cli::oauth_defaults::{build_platform_state, decode_hosted_oauth_state};

        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
        let original = std::env::var("IRONCLAW_INSTANCE_NAME").ok();
@@ -965,7 +1111,11 @@ mod tests {
            std::env::remove_var("IRONCLAW_INSTANCE_NAME");
            std::env::remove_var("OPENCLAW_INSTANCE_NAME");
        }
-        assert_eq!(build_platform_state("abc123"), "abc123");
+        let encoded = build_platform_state("abc123");
+        let decoded = decode_hosted_oauth_state(&encoded).expect("decode hosted state");
+        assert_eq!(decoded.flow_id, "abc123");
+        assert_eq!(decoded.instance_name, None);
+        assert!(!decoded.is_legacy);
        unsafe {
            if let Some(val) = original {
                std::env::set_var("IRONCLAW_INSTANCE_NAME", val);
@@ -978,7 +1128,7 @@ mod tests {

    #[test]
    fn test_build_platform_state_with_openclaw_instance() {
-        use crate::cli::oauth_defaults::build_platform_state;
+        use crate::cli::oauth_defaults::{build_platform_state, decode_hosted_oauth_state};

        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
        let original_ic = std::env::var("IRONCLAW_INSTANCE_NAME").ok();
@@ -988,7 +1138,11 @@ mod tests {
            std::env::remove_var("IRONCLAW_INSTANCE_NAME");
            std::env::set_var("OPENCLAW_INSTANCE_NAME", "quiet-lion");
        }
-        assert_eq!(build_platform_state("xyz789"), "quiet-lion:xyz789");
+        let encoded = build_platform_state("xyz789");
+        let decoded = decode_hosted_oauth_state(&encoded).expect("decode hosted state");
+        assert_eq!(decoded.flow_id, "xyz789");
+        assert_eq!(decoded.instance_name.as_deref(), Some("quiet-lion"));
+        assert!(!decoded.is_legacy);
        unsafe {
            if let Some(val) = original_ic {
                std::env::set_var("IRONCLAW_INSTANCE_NAME", val);
@@ -1017,6 +1171,42 @@ mod tests {
        assert_eq!(strip_instance_prefix(""), "");
    }

+    #[test]
+    fn test_decode_hosted_oauth_state_accepts_legacy_formats() {
+        use crate::cli::oauth_defaults::decode_hosted_oauth_state;
+
+        let decoded = decode_hosted_oauth_state("kind-deer:abc123").expect("legacy prefixed");
+        assert_eq!(decoded.flow_id, "abc123");
+        assert_eq!(decoded.instance_name.as_deref(), Some("kind-deer"));
+        assert!(decoded.is_legacy);
+
+        let decoded = decode_hosted_oauth_state("abc123").expect("legacy raw");
+        assert_eq!(decoded.flow_id, "abc123");
+        assert_eq!(decoded.instance_name, None);
+        assert!(decoded.is_legacy);
+    }
+
+    #[test]
+    fn test_decode_hosted_oauth_state_falls_back_for_non_envelope_ic2_prefix() {
+        use crate::cli::oauth_defaults::decode_hosted_oauth_state;
+
+        let decoded =
+            decode_hosted_oauth_state("ic2.provider-owned-state").expect("prefixed fallback");
+        assert_eq!(decoded.flow_id, "ic2.provider-owned-state");
+        assert_eq!(decoded.instance_name, None);
+        assert!(decoded.is_legacy);
+    }
+
+    #[test]
+    fn test_decode_hosted_oauth_state_rejects_tampered_checksum() {
+        use crate::cli::oauth_defaults::{decode_hosted_oauth_state, encode_hosted_oauth_state};
+
+        let encoded = encode_hosted_oauth_state("abc123", Some("kind-deer"));
+        let tampered = format!("{encoded}broken");
+        let err = decode_hosted_oauth_state(&tampered).expect_err("tampered state should fail");
+        assert!(err.contains("checksum"), "unexpected error: {err}");
+    }
+
    /// Verify that `build_oauth_url` includes the RFC 8707 `resource` parameter
    /// when passed through `extra_params`, which is how MCP OAuth gateway mode
    /// scopes tokens to a specific MCP server.
@@ -292,6 +292,16 @@ async fn list(

 // ── Create ──────────────────────────────────────────────────

+fn cli_notify_config(notify_channel: Option<String>) -> NotifyConfig {
+    NotifyConfig {
+        channel: notify_channel,
+        user: None,
+        on_attention: true,
+        on_failure: true,
+        on_success: false,
+    }
+}
+
 #[allow(clippy::too_many_arguments)]
 async fn create(
    db: &Arc<dyn Database>,
@@ -338,13 +348,7 @@ async fn create(
            max_concurrent: 1,
            dedup_window: None,
        },
-        notify: NotifyConfig {
-            channel: notify_channel,
-            user: user_id.to_string(),
-            on_attention: true,
-            on_failure: true,
-            on_success: false,
-        },
+        notify: cli_notify_config(notify_channel),
        last_run_at: None,
        next_fire_at: next_fire,
        run_count: 0,
@@ -729,4 +733,14 @@ mod tests {
        // Must be valid UTF-8 (would have panicked otherwise).
        assert!(result.is_char_boundary(result.len()));
    }
+
+    #[test]
+    fn cli_notify_config_defaults_to_runtime_target_resolution() {
+        let notify = cli_notify_config(Some("telegram".to_string()));
+        assert_eq!(notify.channel.as_deref(), Some("telegram")); // safety: test-only assertion
+        assert_eq!(notify.user, None); // safety: test-only assertion
+        assert!(notify.on_attention); // safety: test-only assertion
+        assert!(notify.on_failure); // safety: test-only assertion
+        assert!(!notify.on_success); // safety: test-only assertion
+    }
 }
@@ -651,8 +651,8 @@ async fn auth_tool(name: String, dir: Option<PathBuf>, user_id: String) -> anyho

    // Check for OAuth configuration
    if let Some(ref oauth) = auth.oauth {
-        // For providers with shared tokens (e.g., all Google tools share google_oauth_token),
-        // combine scopes from all installed tools so one auth covers everything.
+        // For providers with shared tokens, combine scopes from all installed
+        // tools so one auth covers everything.
        let combined = combine_provider_scopes(&tools_dir, &auth.secret_name, oauth).await;
        if combined.scopes.len() > oauth.scopes.len() {
            let extra = combined.scopes.len() - oauth.scopes.len();
@@ -670,8 +670,8 @@ async fn auth_tool(name: String, dir: Option<PathBuf>, user_id: String) -> anyho
 }

 /// Scan the tools directory for all capabilities files sharing the same secret_name
-/// and combine their OAuth scopes. This way, authing any Google tool requests scopes
-/// for ALL installed Google tools, so one login covers everything.
+/// and combine their OAuth scopes so one authorization covers the full shared
+/// credential set.
 async fn combine_provider_scopes(
    tools_dir: &Path,
    secret_name: &str,
@@ -736,11 +736,18 @@ async fn auth_tool_oauth(
        })
        .or_else(|| builtin.as_ref().map(|c| c.client_id.to_string()))
        .ok_or_else(|| {
-            anyhow::anyhow!(
+            let mut message = format!(
                "OAuth client_id not configured.\n\
-                 Set {} env var, or build with IRONCLAW_GOOGLE_CLIENT_ID.",
+                 Set {} env var",
                oauth.client_id_env.as_deref().unwrap_or("the client_id")
-            )
+            );
+            if let Some(override_env) =
+                oauth_defaults::builtin_client_id_override_env(&auth.secret_name)
+            {
+                message.push_str(&format!(", or build with {override_env}"));
+            }
+            message.push('.');
+            anyhow::anyhow!(message)
        })?;

    // Get client_secret: capabilities file > runtime env var > built-in defaults
@@ -32,13 +32,16 @@ impl Default for BuilderModeConfig {
 }

 impl BuilderModeConfig {
-    pub(crate) fn resolve() -> Result<Self, ConfigError> {
+    pub(crate) fn resolve(settings: &crate::settings::Settings) -> Result<Self, ConfigError> {
+        let bs = &settings.builder;
        Ok(Self {
-            enabled: parse_bool_env("BUILDER_ENABLED", true)?,
-            build_dir: optional_env("BUILDER_DIR")?.map(PathBuf::from),
-            max_iterations: parse_optional_env("BUILDER_MAX_ITERATIONS", 20)?,
-            timeout_secs: parse_optional_env("BUILDER_TIMEOUT_SECS", 600)?,
-            auto_register: parse_bool_env("BUILDER_AUTO_REGISTER", true)?,
+            enabled: parse_bool_env("BUILDER_ENABLED", bs.enabled)?,
+            build_dir: optional_env("BUILDER_DIR")?
+                .map(PathBuf::from)
+                .or_else(|| bs.build_dir.clone()),
+            max_iterations: parse_optional_env("BUILDER_MAX_ITERATIONS", bs.max_iterations)?,
+            timeout_secs: parse_optional_env("BUILDER_TIMEOUT_SECS", bs.timeout_secs)?,
+            auto_register: parse_bool_env("BUILDER_AUTO_REGISTER", bs.auto_register)?,
        })
    }

@@ -56,3 +59,36 @@ impl BuilderModeConfig {
        }
    }
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use crate::config::helpers::ENV_MUTEX;
+    use crate::settings::Settings;
+
+    #[test]
+    fn resolve_falls_back_to_settings() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        let mut settings = Settings::default();
+        settings.builder.max_iterations = 99;
+        settings.builder.auto_register = false;
+
+        let cfg = BuilderModeConfig::resolve(&settings).expect("resolve");
+        assert_eq!(cfg.max_iterations, 99);
+        assert!(!cfg.auto_register);
+    }
+
+    #[test]
+    fn env_overrides_settings() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        let mut settings = Settings::default();
+        settings.builder.timeout_secs = 123;
+
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe { std::env::set_var("BUILDER_TIMEOUT_SECS", "3") };
+        let cfg = BuilderModeConfig::resolve(&settings).expect("resolve");
+        unsafe { std::env::remove_var("BUILDER_TIMEOUT_SECS") };
+
+        assert_eq!(cfg.timeout_secs, 3);
+    }
+}
@@ -91,36 +91,24 @@ pub struct SignalConfig {
 }

 impl ChannelsConfig {
-    /// Resolve channels config following `env > settings > default` for every field.
-    pub(crate) fn resolve(settings: &Settings, tunnel_enabled: bool) -> Result<Self, ConfigError> {
+    pub(crate) fn resolve(settings: &Settings, owner_id: &str) -> Result<Self, ConfigError> {
        let cs = &settings.channels;

-        // --- HTTP webhook ---
-        // HTTP is enabled when env vars are set OR settings has it enabled.
        let http_enabled_by_env =
            optional_env("HTTP_PORT")?.is_some() || optional_env("HTTP_HOST")?.is_some();
-        // When a tunnel is configured, default to loopback since external
-        // traffic arrives through the tunnel. Without a tunnel the webhook
-        // server needs to accept connections from the network directly.
-        let default_host = if tunnel_enabled {
-            "127.0.0.1"
-        } else {
-            "0.0.0.0"
-        };
        let http = if http_enabled_by_env || cs.http_enabled {
            Some(HttpConfig {
                host: optional_env("HTTP_HOST")?
                    .or_else(|| cs.http_host.clone())
-                    .unwrap_or_else(|| default_host.to_string()),
+                    .unwrap_or_else(|| "0.0.0.0".to_string()),
                port: parse_optional_env("HTTP_PORT", cs.http_port.unwrap_or(8080))?,
                webhook_secret: optional_env("HTTP_WEBHOOK_SECRET")?.map(SecretString::from),
-                user_id: optional_env("HTTP_USER_ID")?.unwrap_or_else(|| "http".to_string()),
+                user_id: owner_id.to_string(),
            })
        } else {
            None
        };

-        // --- Web gateway ---
        let gateway_enabled = parse_bool_env("GATEWAY_ENABLED", cs.gateway_enabled)?;
        let gateway = if gateway_enabled {
            Some(GatewayConfig {
@@ -133,33 +121,29 @@ impl ChannelsConfig {
                )?,
                auth_token: optional_env("GATEWAY_AUTH_TOKEN")?
                    .or_else(|| cs.gateway_auth_token.clone()),
-                user_id: optional_env("GATEWAY_USER_ID")?
-                    .or_else(|| cs.gateway_user_id.clone())
-                    .unwrap_or_else(|| "default".to_string()),
+                user_id: owner_id.to_string(),
            })
        } else {
            None
        };

-        // --- Signal ---
        let signal_url = optional_env("SIGNAL_HTTP_URL")?.or_else(|| cs.signal_http_url.clone());
        let signal = if let Some(http_url) = signal_url {
            let account = optional_env("SIGNAL_ACCOUNT")?
                .or_else(|| cs.signal_account.clone())
                .ok_or(ConfigError::InvalidValue {
                    key: "SIGNAL_ACCOUNT".to_string(),
-                    message: "SIGNAL_ACCOUNT is required when Signal is enabled".to_string(),
+                    message: "SIGNAL_ACCOUNT is required when SIGNAL_HTTP_URL is set".to_string(),
                })?;
-            let allow_from_str =
-                optional_env("SIGNAL_ALLOW_FROM")?.or_else(|| cs.signal_allow_from.clone());
-            let allow_from = match allow_from_str {
-                None => vec![account.clone()],
-                Some(s) => s
-                    .split(',')
-                    .map(|e| e.trim().to_string())
-                    .filter(|s| !s.is_empty())
-                    .collect(),
-            };
+            let allow_from =
+                match optional_env("SIGNAL_ALLOW_FROM")?.or_else(|| cs.signal_allow_from.clone()) {
+                    None => vec![account.clone()],
+                    Some(s) => s
+                        .split(',')
+                        .map(|e| e.trim().to_string())
+                        .filter(|s| !s.is_empty())
+                        .collect(),
+                };
            let dm_policy = optional_env("SIGNAL_DM_POLICY")?
                .or_else(|| cs.signal_dm_policy.clone())
                .unwrap_or_else(|| "pairing".to_string());
@@ -201,18 +185,8 @@ impl ChannelsConfig {
            None
        };

-        // --- CLI ---
        let cli_enabled = parse_bool_env("CLI_ENABLED", cs.cli_enabled)?;

-        // --- WASM channels ---
-        let wasm_channels_dir = optional_env("WASM_CHANNELS_DIR")?
-            .map(PathBuf::from)
-            .or_else(|| cs.wasm_channels_dir.clone())
-            .unwrap_or_else(default_channels_dir);
-
-        let wasm_channels_enabled =
-            parse_bool_env("WASM_CHANNELS_ENABLED", cs.wasm_channels_enabled)?;
-
        Ok(Self {
            cli: CliConfig {
                enabled: cli_enabled,
@@ -220,8 +194,14 @@ impl ChannelsConfig {
            http,
            gateway,
            signal,
-            wasm_channels_dir,
-            wasm_channels_enabled,
+            wasm_channels_dir: optional_env("WASM_CHANNELS_DIR")?
+                .map(PathBuf::from)
+                .or_else(|| cs.wasm_channels_dir.clone())
+                .unwrap_or_else(default_channels_dir),
+            wasm_channels_enabled: parse_bool_env(
+                "WASM_CHANNELS_ENABLED",
+                cs.wasm_channels_enabled,
+            )?,
            wasm_channel_owner_ids: {
                let mut ids = cs.wasm_channel_owner_ids.clone();
                // Backwards compat: TELEGRAM_OWNER_ID env var
@@ -252,6 +232,8 @@ fn default_channels_dir() -> PathBuf {
 #[cfg(test)]
 mod tests {
    use crate::config::channels::*;
+    use crate::config::helpers::ENV_MUTEX;
+    use crate::settings::Settings;

    #[test]
    fn cli_config_fields() {
@@ -398,69 +380,6 @@ mod tests {
        assert!(!cfg.wasm_channels_enabled);
    }

-    /// When a tunnel is active and HTTP_HOST is not explicitly set, the
-    /// webhook server should default to loopback to avoid unnecessary exposure.
-    #[test]
-    fn http_host_defaults_to_loopback_with_tunnel() {
-        // Set HTTP_PORT to trigger HttpConfig creation, but leave HTTP_HOST unset
-        // so the default kicks in.
-        unsafe {
-            std::env::set_var("HTTP_PORT", "9999");
-            std::env::remove_var("HTTP_HOST");
-        }
-        let settings = crate::settings::Settings::default();
-        let cfg = ChannelsConfig::resolve(&settings, true).unwrap();
-        unsafe {
-            std::env::remove_var("HTTP_PORT");
-        }
-        let http = cfg.http.expect("HttpConfig should be present");
-        assert_eq!(
-            http.host, "127.0.0.1",
-            "tunnel active should default to loopback"
-        );
-        assert_eq!(http.port, 9999);
-    }
-
-    /// Without a tunnel, the webhook server defaults to 0.0.0.0 so external
-    /// services can reach it directly.
-    #[test]
-    fn http_host_defaults_to_all_interfaces_without_tunnel() {
-        unsafe {
-            std::env::set_var("HTTP_PORT", "9998");
-            std::env::remove_var("HTTP_HOST");
-        }
-        let settings = crate::settings::Settings::default();
-        let cfg = ChannelsConfig::resolve(&settings, false).unwrap();
-        unsafe {
-            std::env::remove_var("HTTP_PORT");
-        }
-        let http = cfg.http.expect("HttpConfig should be present");
-        assert_eq!(
-            http.host, "0.0.0.0",
-            "no tunnel should default to all interfaces"
-        );
-    }
-
-    /// An explicit HTTP_HOST always wins regardless of tunnel state.
-    #[test]
-    fn explicit_http_host_overrides_tunnel_default() {
-        unsafe {
-            std::env::set_var("HTTP_PORT", "9997");
-            std::env::set_var("HTTP_HOST", "192.168.1.50");
-        }
-        let settings = crate::settings::Settings::default();
-        let cfg = ChannelsConfig::resolve(&settings, true).unwrap();
-        unsafe {
-            std::env::remove_var("HTTP_PORT");
-            std::env::remove_var("HTTP_HOST");
-        }
-        let http = cfg.http.expect("HttpConfig should be present");
-        assert_eq!(
-            http.host, "192.168.1.50",
-            "explicit host should override tunnel default"
-        );
-    }
-
    #[test]
    fn default_channels_dir_ends_with_channels() {
        let dir = default_channels_dir();
@@ -471,242 +390,43 @@ mod tests {
    }

    #[test]
-    fn default_gateway_port_constant() {
-        assert_eq!(DEFAULT_GATEWAY_PORT, 3000);
-    }
-
-    /// With default settings and no env vars, gateway should use defaults.
-    #[test]
-    fn resolve_gateway_defaults_from_settings() {
-        let _lock = crate::config::helpers::ENV_MUTEX.lock();
-        // Clear env vars that would interfere
-        unsafe {
-            std::env::remove_var("GATEWAY_ENABLED");
-            std::env::remove_var("GATEWAY_HOST");
-            std::env::remove_var("GATEWAY_PORT");
-            std::env::remove_var("GATEWAY_AUTH_TOKEN");
-            std::env::remove_var("GATEWAY_USER_ID");
-            std::env::remove_var("HTTP_PORT");
-            std::env::remove_var("HTTP_HOST");
-            std::env::remove_var("SIGNAL_HTTP_URL");
-            std::env::remove_var("CLI_ENABLED");
-            std::env::remove_var("WASM_CHANNELS_DIR");
-            std::env::remove_var("WASM_CHANNELS_ENABLED");
-            std::env::remove_var("TELEGRAM_OWNER_ID");
-        }
-
-        let settings = crate::settings::Settings::default();
-        let cfg = ChannelsConfig::resolve(&settings, false).unwrap();
-
-        let gw = cfg.gateway.expect("gateway should be enabled by default");
-        assert_eq!(gw.host, "127.0.0.1");
-        assert_eq!(gw.port, DEFAULT_GATEWAY_PORT);
-        assert!(gw.auth_token.is_none());
-        assert_eq!(gw.user_id, "default");
-    }
-
-    /// Settings values should be used when no env vars are set.
-    #[test]
-    fn resolve_gateway_from_settings() {
-        let _lock = crate::config::helpers::ENV_MUTEX.lock();
-        unsafe {
-            std::env::remove_var("GATEWAY_ENABLED");
-            std::env::remove_var("GATEWAY_HOST");
-            std::env::remove_var("GATEWAY_PORT");
-            std::env::remove_var("GATEWAY_AUTH_TOKEN");
-            std::env::remove_var("GATEWAY_USER_ID");
-            std::env::remove_var("HTTP_PORT");
-            std::env::remove_var("HTTP_HOST");
-            std::env::remove_var("SIGNAL_HTTP_URL");
-            std::env::remove_var("CLI_ENABLED");
-            std::env::remove_var("WASM_CHANNELS_DIR");
-            std::env::remove_var("WASM_CHANNELS_ENABLED");
-            std::env::remove_var("TELEGRAM_OWNER_ID");
-        }
-
-        let mut settings = crate::settings::Settings::default();
-        settings.channels.gateway_port = Some(4000);
-        settings.channels.gateway_host = Some("0.0.0.0".to_string());
-        settings.channels.gateway_auth_token = Some("db-token-123".to_string());
-        settings.channels.gateway_user_id = Some("myuser".to_string());
-
-        let cfg = ChannelsConfig::resolve(&settings, false).unwrap();
-        let gw = cfg.gateway.expect("gateway should be enabled");
-        assert_eq!(gw.port, 4000);
-        assert_eq!(gw.host, "0.0.0.0");
-        assert_eq!(gw.auth_token.as_deref(), Some("db-token-123"));
-        assert_eq!(gw.user_id, "myuser");
-    }
-
-    /// Env vars should override settings values.
-    #[test]
-    fn resolve_env_overrides_settings() {
-        let _lock = crate::config::helpers::ENV_MUTEX.lock();
-        unsafe {
-            std::env::set_var("GATEWAY_PORT", "5000");
-            std::env::set_var("GATEWAY_HOST", "10.0.0.1");
-            std::env::set_var("GATEWAY_AUTH_TOKEN", "env-token");
-            std::env::remove_var("GATEWAY_ENABLED");
-            std::env::remove_var("GATEWAY_USER_ID");
-            std::env::remove_var("HTTP_PORT");
-            std::env::remove_var("HTTP_HOST");
-            std::env::remove_var("SIGNAL_HTTP_URL");
-            std::env::remove_var("CLI_ENABLED");
-            std::env::remove_var("WASM_CHANNELS_DIR");
-            std::env::remove_var("WASM_CHANNELS_ENABLED");
-            std::env::remove_var("TELEGRAM_OWNER_ID");
-        }
-
-        let mut settings = crate::settings::Settings::default();
-        settings.channels.gateway_port = Some(4000);
-        settings.channels.gateway_host = Some("0.0.0.0".to_string());
-        settings.channels.gateway_auth_token = Some("db-token".to_string());
-
-        let cfg = ChannelsConfig::resolve(&settings, false).unwrap();
-        let gw = cfg.gateway.expect("gateway should be enabled");
-        assert_eq!(gw.port, 5000, "env should override settings");
-        assert_eq!(gw.host, "10.0.0.1", "env should override settings");
-        assert_eq!(
-            gw.auth_token.as_deref(),
-            Some("env-token"),
-            "env should override settings"
-        );
-
-        // Cleanup
-        unsafe {
-            std::env::remove_var("GATEWAY_PORT");
-            std::env::remove_var("GATEWAY_HOST");
-            std::env::remove_var("GATEWAY_AUTH_TOKEN");
-        }
-    }
-
-    /// CLI enabled should fall back to settings.
-    #[test]
-    fn resolve_cli_enabled_from_settings() {
-        let _lock = crate::config::helpers::ENV_MUTEX.lock();
-        unsafe {
-            std::env::remove_var("CLI_ENABLED");
-            std::env::remove_var("GATEWAY_ENABLED");
-            std::env::remove_var("GATEWAY_HOST");
-            std::env::remove_var("GATEWAY_PORT");
-            std::env::remove_var("GATEWAY_AUTH_TOKEN");
-            std::env::remove_var("GATEWAY_USER_ID");
-            std::env::remove_var("HTTP_PORT");
-            std::env::remove_var("HTTP_HOST");
-            std::env::remove_var("SIGNAL_HTTP_URL");
-            std::env::remove_var("WASM_CHANNELS_DIR");
-            std::env::remove_var("WASM_CHANNELS_ENABLED");
-            std::env::remove_var("TELEGRAM_OWNER_ID");
-        }
-
-        let mut settings = crate::settings::Settings::default();
-        settings.channels.cli_enabled = false;
-
-        let cfg = ChannelsConfig::resolve(&settings, false).unwrap();
-        assert!(!cfg.cli.enabled, "settings should disable CLI");
-    }
-
-    /// HTTP channel should activate when settings has it enabled.
-    #[test]
-    fn resolve_http_from_settings() {
-        let _lock = crate::config::helpers::ENV_MUTEX.lock();
-        unsafe {
-            std::env::remove_var("HTTP_PORT");
-            std::env::remove_var("HTTP_HOST");
-            std::env::remove_var("HTTP_WEBHOOK_SECRET");
-            std::env::remove_var("HTTP_USER_ID");
-            std::env::remove_var("GATEWAY_ENABLED");
-            std::env::remove_var("GATEWAY_HOST");
-            std::env::remove_var("GATEWAY_PORT");
-            std::env::remove_var("GATEWAY_AUTH_TOKEN");
-            std::env::remove_var("GATEWAY_USER_ID");
-            std::env::remove_var("SIGNAL_HTTP_URL");
-            std::env::remove_var("CLI_ENABLED");
-            std::env::remove_var("WASM_CHANNELS_DIR");
-            std::env::remove_var("WASM_CHANNELS_ENABLED");
-            std::env::remove_var("TELEGRAM_OWNER_ID");
-        }
-
-        let mut settings = crate::settings::Settings::default();
+    fn resolve_uses_settings_channel_values_with_owner_scope_user_ids() {
+        let _guard = ENV_MUTEX.lock().unwrap_or_else(|e| e.into_inner());
+        let mut settings = Settings::default();
        settings.channels.http_enabled = true;
-        settings.channels.http_port = Some(9090);
-        settings.channels.http_host = Some("10.0.0.1".to_string());
+        settings.channels.http_host = Some("127.0.0.2".to_string());
+        settings.channels.http_port = Some(8181);
+        settings.channels.gateway_enabled = true;
+        settings.channels.gateway_host = Some("127.0.0.3".to_string());
+        settings.channels.gateway_port = Some(9191);
+        settings.channels.gateway_auth_token = Some("tok".to_string());
+        settings.channels.signal_http_url = Some("http://127.0.0.1:8080".to_string());
+        settings.channels.signal_account = Some("+15551234567".to_string());
+        settings.channels.signal_allow_from = Some("+15551234567,+15557654321".to_string());
+        settings.channels.wasm_channels_dir = Some(PathBuf::from("/tmp/settings-channels"));
+        settings.channels.wasm_channels_enabled = false;

-        let cfg = ChannelsConfig::resolve(&settings, false).unwrap();
-        let http = cfg.http.expect("HTTP should be enabled from settings");
-        assert_eq!(http.port, 9090);
-        assert_eq!(http.host, "10.0.0.1");
-    }
+        let cfg = ChannelsConfig::resolve(&settings, "owner-scope").expect("resolve");

-    /// Settings round-trip through DB map for new gateway fields.
-    #[test]
-    fn settings_gateway_fields_db_roundtrip() {
-        let mut settings = crate::settings::Settings::default();
-        settings.channels.gateway_port = Some(4000);
-        settings.channels.gateway_host = Some("0.0.0.0".to_string());
-        settings.channels.gateway_auth_token = Some("tok-abc".to_string());
-        settings.channels.gateway_user_id = Some("myuser".to_string());
-        settings.channels.cli_enabled = false;
+        let http = cfg.http.expect("http config");
+        assert_eq!(http.host, "127.0.0.2");
+        assert_eq!(http.port, 8181);
+        assert_eq!(http.user_id, "owner-scope");

-        let map = settings.to_db_map();
-        let restored = crate::settings::Settings::from_db_map(&map);
+        let gateway = cfg.gateway.expect("gateway config");
+        assert_eq!(gateway.host, "127.0.0.3");
+        assert_eq!(gateway.port, 9191);
+        assert_eq!(gateway.auth_token.as_deref(), Some("tok"));
+        assert_eq!(gateway.user_id, "owner-scope");
+
+        let signal = cfg.signal.expect("signal config");
+        assert_eq!(signal.account, "+15551234567");
+        assert_eq!(signal.allow_from, vec!["+15551234567", "+15557654321"]);

-        assert_eq!(restored.channels.gateway_port, Some(4000));
-        assert_eq!(restored.channels.gateway_host.as_deref(), Some("0.0.0.0"));
        assert_eq!(
-            restored.channels.gateway_auth_token.as_deref(),
-            Some("tok-abc")
+            cfg.wasm_channels_dir,
+            PathBuf::from("/tmp/settings-channels")
        );
-        assert_eq!(restored.channels.gateway_user_id.as_deref(), Some("myuser"));
-        assert!(!restored.channels.cli_enabled);
-    }
-
-    /// Invalid boolean env values must produce errors, not silently degrade.
-    #[test]
-    fn resolve_rejects_invalid_bool_env() {
-        let _lock = crate::config::helpers::ENV_MUTEX.lock();
-        let settings = crate::settings::Settings::default();
-
-        // GATEWAY_ENABLED=maybe should error
-        unsafe {
-            std::env::set_var("GATEWAY_ENABLED", "maybe");
-            std::env::remove_var("HTTP_PORT");
-            std::env::remove_var("HTTP_HOST");
-            std::env::remove_var("SIGNAL_HTTP_URL");
-            std::env::remove_var("CLI_ENABLED");
-            std::env::remove_var("WASM_CHANNELS_ENABLED");
-            std::env::remove_var("GATEWAY_PORT");
-            std::env::remove_var("GATEWAY_HOST");
-            std::env::remove_var("GATEWAY_AUTH_TOKEN");
-            std::env::remove_var("GATEWAY_USER_ID");
-            std::env::remove_var("WASM_CHANNELS_DIR");
-            std::env::remove_var("TELEGRAM_OWNER_ID");
-        }
-        let result = ChannelsConfig::resolve(&settings, false);
-        assert!(result.is_err(), "GATEWAY_ENABLED=maybe should be rejected");
-
-        // CLI_ENABLED=on should error
-        unsafe {
-            std::env::remove_var("GATEWAY_ENABLED");
-            std::env::set_var("CLI_ENABLED", "on");
-        }
-        let result = ChannelsConfig::resolve(&settings, false);
-        assert!(result.is_err(), "CLI_ENABLED=on should be rejected");
-
-        // WASM_CHANNELS_ENABLED=yes should error
-        unsafe {
-            std::env::remove_var("CLI_ENABLED");
-            std::env::set_var("WASM_CHANNELS_ENABLED", "yes");
-        }
-        let result = ChannelsConfig::resolve(&settings, false);
-        assert!(
-            result.is_err(),
-            "WASM_CHANNELS_ENABLED=yes should be rejected"
-        );
-
-        // Cleanup
-        unsafe {
-            std::env::remove_var("WASM_CHANNELS_ENABLED");
-        }
+        assert!(!cfg.wasm_channels_enabled);
    }
 }
@@ -8,6 +8,9 @@ use crate::llm::SessionManager;
 use crate::settings::Settings;
 use crate::workspace::EmbeddingProvider;

+/// Default maximum number of cached embeddings.
+pub const DEFAULT_EMBEDDING_CACHE_SIZE: usize = 10_000;
+
 /// Embeddings provider configuration.
 #[derive(Debug, Clone)]
 pub struct EmbeddingsConfig {
@@ -26,6 +29,12 @@ pub struct EmbeddingsConfig {
    /// Custom base URL for OpenAI-compatible embedding providers.
    /// When set, overrides the default `https://api.openai.com`.
    pub openai_base_url: Option<String>,
+    /// Maximum entries in the embedding LRU cache (default 10,000).
+    ///
+    /// Approximate raw embedding payload: `cache_size × dimension × 4 bytes`.
+    /// 10,000 × 1536 floats ≈ 58 MB (payload only; actual memory is higher
+    /// due to HashMap buckets, per-entry Vec/timestamp overhead).
+    pub cache_size: usize,
 }

 impl Default for EmbeddingsConfig {
@@ -40,6 +49,7 @@ impl Default for EmbeddingsConfig {
            ollama_base_url: "http://localhost:11434".to_string(),
            dimension,
            openai_base_url: None,
+            cache_size: DEFAULT_EMBEDDING_CACHE_SIZE,
        }
    }
 }
@@ -80,6 +90,15 @@ impl EmbeddingsConfig {

        let openai_base_url = optional_env("EMBEDDING_BASE_URL")?;

+        let cache_size = parse_optional_env("EMBEDDING_CACHE_SIZE", DEFAULT_EMBEDDING_CACHE_SIZE)?;
+
+        if cache_size == 0 {
+            return Err(ConfigError::InvalidValue {
+                key: "EMBEDDING_CACHE_SIZE".to_string(),
+                message: "must be at least 1".to_string(),
+            });
+        }
+
        Ok(Self {
            enabled,
            provider,
@@ -88,6 +107,7 @@ impl EmbeddingsConfig {
            ollama_base_url,
            dimension,
            openai_base_url,
+            cache_size,
        })
    }

@@ -183,13 +203,13 @@ mod tests {
            std::env::remove_var("EMBEDDING_MODEL");
            std::env::remove_var("OPENAI_API_KEY");
            std::env::remove_var("EMBEDDING_BASE_URL");
+            std::env::remove_var("EMBEDDING_CACHE_SIZE");
        }
    }

    #[test]
    fn embeddings_disabled_not_overridden_by_openai_key() {
        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
-
        clear_embedding_env();
        // SAFETY: Under ENV_MUTEX, no concurrent env access.
        unsafe {
@@ -240,7 +260,6 @@ mod tests {
    #[test]
    fn embeddings_env_override_takes_precedence() {
        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
-
        clear_embedding_env();
        // SAFETY: Under ENV_MUTEX.
        unsafe {
@@ -281,10 +300,8 @@ mod tests {
        let config = EmbeddingsConfig::resolve(&settings).expect("resolve should succeed");
        assert_eq!(
            config.openai_base_url.as_deref(),
-            Some("https://custom.example.com"),
-            "EMBEDDING_BASE_URL env var should be parsed into openai_base_url"
+            Some("https://custom.example.com")
        );
-
        // SAFETY: Under ENV_MUTEX.
        unsafe {
            std::env::remove_var("EMBEDDING_BASE_URL");
@@ -303,4 +320,24 @@ mod tests {
            "openai_base_url should be None when EMBEDDING_BASE_URL is not set"
        );
    }
+
+    #[test]
+    fn cache_size_zero_rejected() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        clear_embedding_env();
+        // SAFETY: Under ENV_MUTEX.
+        unsafe {
+            std::env::set_var("EMBEDDING_CACHE_SIZE", "0");
+        }
+
+        let settings = Settings::default();
+        let result = EmbeddingsConfig::resolve(&settings);
+        assert!(result.is_err(), "cache_size=0 should be rejected");
+        let err = result.unwrap_err().to_string();
+        assert!(err.contains("at least 1"), "should mention minimum: {err}");
+        // SAFETY: Under ENV_MUTEX.
+        unsafe {
+            std::env::remove_var("EMBEDDING_CACHE_SIZE");
+        }
+    }
 }
@@ -7,17 +7,19 @@ use crate::settings::Settings;
 pub struct HeartbeatConfig {
    /// Whether heartbeat is enabled.
    pub enabled: bool,
-    /// Interval between heartbeat checks in seconds.
+    /// Interval between heartbeat checks in seconds (used when fire_at is not set).
    pub interval_secs: u64,
    /// Channel to notify on heartbeat findings.
    pub notify_channel: Option<String>,
    /// User ID to notify on heartbeat findings.
    pub notify_user: Option<String>,
+    /// Fixed time-of-day to fire (HH:MM, 24h). When set, interval_secs is ignored.
+    pub fire_at: Option<chrono::NaiveTime>,
    /// Hour (0-23) when quiet hours start.
    pub quiet_hours_start: Option<u32>,
    /// Hour (0-23) when quiet hours end.
    pub quiet_hours_end: Option<u32>,
-    /// Timezone for quiet hours evaluation (IANA name).
+    /// Timezone for fire_at and quiet hours evaluation (IANA name).
    pub timezone: Option<String>,
 }

@@ -28,6 +30,7 @@ impl Default for HeartbeatConfig {
            interval_secs: 1800, // 30 minutes
            notify_channel: None,
            notify_user: None,
+            fire_at: None,
            quiet_hours_start: None,
            quiet_hours_end: None,
            timezone: None,
@@ -37,6 +40,19 @@ impl Default for HeartbeatConfig {

 impl HeartbeatConfig {
    pub(crate) fn resolve(settings: &Settings) -> Result<Self, ConfigError> {
+        let fire_at_str =
+            optional_env("HEARTBEAT_FIRE_AT")?.or_else(|| settings.heartbeat.fire_at.clone());
+        let fire_at = fire_at_str
+            .map(|s| {
+                chrono::NaiveTime::parse_from_str(&s, "%H:%M").map_err(|e| {
+                    ConfigError::InvalidValue {
+                        key: "HEARTBEAT_FIRE_AT".to_string(),
+                        message: format!("must be HH:MM (24h), e.g. '14:00': {e}"),
+                    }
+                })
+            })
+            .transpose()?;
+
        Ok(Self {
            enabled: parse_bool_env("HEARTBEAT_ENABLED", settings.heartbeat.enabled)?,
            interval_secs: parse_optional_env(
@@ -47,6 +63,7 @@ impl HeartbeatConfig {
                .or_else(|| settings.heartbeat.notify_channel.clone()),
            notify_user: optional_env("HEARTBEAT_NOTIFY_USER")?
                .or_else(|| settings.heartbeat.notify_user.clone()),
+            fire_at,
            quiet_hours_start: parse_option_env::<u32>("HEARTBEAT_QUIET_START")?
                .or(settings.heartbeat.quiet_hours_start)
                .map(|h| {
@@ -9,7 +9,6 @@ use crate::llm::config::*;
 use crate::llm::registry::{ProviderProtocol, ProviderRegistry};
 use crate::llm::session::SessionConfig;
 use crate::settings::Settings;
-
 impl LlmConfig {
    /// Create a test-friendly config without reading env vars.
    #[cfg(feature = "libsql")]
@@ -39,6 +38,8 @@ impl LlmConfig {
            provider: None,
            bedrock: None,
            request_timeout_secs: 120,
+            cheap_model: None,
+            smart_routing_cascade: false,
        }
    }

@@ -169,6 +170,14 @@ impl LlmConfig {

        let request_timeout_secs = parse_optional_env("LLM_REQUEST_TIMEOUT_SECS", 120)?;

+        // Generic cheap model (works with any backend).
+        // Falls back to NearAI-specific cheap_model in provider chain logic.
+        let cheap_model = optional_env("LLM_CHEAP_MODEL")?;
+
+        // Generic smart routing cascade flag.
+        // Defaults to true. Overrides NearAI-specific smart_routing_cascade.
+        let smart_routing_cascade = parse_optional_env("SMART_ROUTING_CASCADE", true)?;
+
        Ok(Self {
            backend: if is_nearai {
                "nearai".to_string()
@@ -184,6 +193,8 @@ impl LlmConfig {
            provider,
            bedrock,
            request_timeout_secs,
+            cheap_model,
+            smart_routing_cascade,
        })
    }

@@ -241,8 +252,30 @@ impl LlmConfig {
            )
        };

-        // Resolve API key from env
-        let api_key = if let Some(env_var) = api_key_env {
+        // Codex auth.json override: when LLM_USE_CODEX_AUTH=true,
+        // credentials from the Codex CLI's auth.json take highest priority
+        // (over env vars AND secrets store). In ChatGPT mode, the base URL
+        // is also overridden to the private ChatGPT backend endpoint.
+        let mut codex_base_url_override: Option<String> = None;
+        let codex_creds = if parse_optional_env("LLM_USE_CODEX_AUTH", false)? {
+            let path = optional_env("CODEX_AUTH_PATH")?
+                .map(std::path::PathBuf::from)
+                .unwrap_or_else(crate::llm::codex_auth::default_codex_auth_path);
+            crate::llm::codex_auth::load_codex_credentials(&path)
+        } else {
+            None
+        };
+
+        let codex_refresh_token = codex_creds.as_ref().and_then(|c| c.refresh_token.clone());
+        let codex_auth_path = codex_creds.as_ref().and_then(|c| c.auth_path.clone());
+
+        let api_key = if let Some(creds) = codex_creds {
+            if creds.is_chatgpt_mode {
+                codex_base_url_override = Some(creds.base_url().to_string());
+            }
+            Some(creds.token)
+        } else if let Some(env_var) = api_key_env {
+            // Resolve API key from env (including secrets store overlay)
            optional_env(env_var)?.map(SecretString::from)
        } else {
            None
@@ -259,22 +292,28 @@ impl LlmConfig {
            }
        }

-        // Resolve base URL: env var > settings (backward compat) > registry default
-        let base_url = if let Some(env_var) = base_url_env {
-            optional_env(env_var)?
-        } else {
-            None
-        }
-        .or_else(|| {
-            // Backward compat: check legacy settings fields
-            match backend {
-                "ollama" => settings.ollama_base_url.clone(),
-                "openai_compatible" | "openrouter" => settings.openai_compatible_base_url.clone(),
-                _ => None,
-            }
-        })
-        .or_else(|| default_base_url.map(String::from))
-        .unwrap_or_default();
+        // Resolve base URL: codex override > env var > settings (backward compat) > registry default
+        let is_codex_chatgpt = codex_base_url_override.is_some();
+        let base_url = codex_base_url_override
+            .or_else(|| {
+                if let Some(env_var) = base_url_env {
+                    optional_env(env_var).ok().flatten()
+                } else {
+                    None
+                }
+            })
+            .or_else(|| {
+                // Backward compat: check legacy settings fields
+                match backend {
+                    "ollama" => settings.ollama_base_url.clone(),
+                    "openai_compatible" | "openrouter" => {
+                        settings.openai_compatible_base_url.clone()
+                    }
+                    _ => None,
+                }
+            })
+            .or_else(|| default_base_url.map(String::from))
+            .unwrap_or_default();

        if base_url_required
            && base_url.is_empty()
@@ -340,6 +379,9 @@ impl LlmConfig {
            model,
            extra_headers,
            oauth_token,
+            is_codex_chatgpt,
+            refresh_token: codex_refresh_token,
+            auth_path: codex_auth_path,
            cache_retention,
            unsupported_params,
        })
@@ -26,7 +26,7 @@ mod tunnel;
 mod wasm;

 use std::collections::HashMap;
-use std::sync::{LazyLock, Mutex};
+use std::sync::{LazyLock, Mutex, Once};

 use crate::error::ConfigError;
 use crate::settings::Settings;
@@ -38,7 +38,7 @@ pub use self::channels::{
    ChannelsConfig, CliConfig, DEFAULT_GATEWAY_PORT, GatewayConfig, HttpConfig, SignalConfig,
 };
 pub use self::database::{DatabaseBackend, DatabaseConfig, SslMode, default_libsql_path};
-pub use self::embeddings::EmbeddingsConfig;
+pub use self::embeddings::{DEFAULT_EMBEDDING_CACHE_SIZE, EmbeddingsConfig};
 pub use self::heartbeat::HeartbeatConfig;
 pub use self::hygiene::HygieneConfig;
 pub use self::llm::default_session_path;
@@ -74,10 +74,12 @@ pub use self::helpers::{env_or_override, set_runtime_env};
 /// their data. Whichever runs first initialises the map; the second merges in.
 static INJECTED_VARS: LazyLock<Mutex<HashMap<String, String>>> =
    LazyLock::new(|| Mutex::new(HashMap::new()));
+static WARNED_EXPLICIT_DEFAULT_OWNER_ID: Once = Once::new();

 /// Main configuration for the agent.
 #[derive(Debug, Clone)]
 pub struct Config {
+    pub owner_id: String,
    pub database: DatabaseConfig,
    pub llm: LlmConfig,
    pub embeddings: EmbeddingsConfig,
@@ -118,6 +120,7 @@ impl Config {
        installed_skills_dir: std::path::PathBuf,
    ) -> Self {
        Self {
+            owner_id: "default".to_string(),
            database: DatabaseConfig {
                backend: DatabaseBackend::LibSql,
                url: secrecy::SecretString::from("unused://test".to_string()),
@@ -228,13 +231,7 @@ impl Config {
    pub async fn from_env_with_toml(
        toml_path: Option<&std::path::Path>,
    ) -> Result<Self, ConfigError> {
-        let _ = dotenvy::dotenv();
-        crate::bootstrap::load_ironclaw_env();
-        let mut settings = Settings::load();
-
-        // Overlay TOML config file (values win over JSON settings)
-        Self::apply_toml_overlay(&mut settings, toml_path)?;
-
+        let settings = load_bootstrap_settings(toml_path)?;
        Self::build(&settings).await
    }

@@ -306,26 +303,25 @@ impl Config {

    /// Build config from settings (shared by from_env and from_db).
    async fn build(settings: &Settings) -> Result<Self, ConfigError> {
-        // Resolve tunnel first so channels can default to loopback when a
-        // tunnel handles external exposure (no need to bind 0.0.0.0).
-        let tunnel = TunnelConfig::resolve(settings)?;
+        let owner_id = resolve_owner_id(settings)?;

        Ok(Self {
+            owner_id: owner_id.clone(),
            database: DatabaseConfig::resolve()?,
            llm: LlmConfig::resolve(settings)?,
            embeddings: EmbeddingsConfig::resolve(settings)?,
-            channels: ChannelsConfig::resolve(settings, tunnel.is_enabled())?,
-            tunnel,
+            tunnel: TunnelConfig::resolve(settings)?,
+            channels: ChannelsConfig::resolve(settings, &owner_id)?,
            agent: AgentConfig::resolve(settings)?,
-            safety: resolve_safety_config()?,
-            wasm: WasmConfig::resolve()?,
+            safety: resolve_safety_config(settings)?,
+            wasm: WasmConfig::resolve(settings)?,
            secrets: SecretsConfig::resolve().await?,
-            builder: BuilderModeConfig::resolve()?,
+            builder: BuilderModeConfig::resolve(settings)?,
            heartbeat: HeartbeatConfig::resolve(settings)?,
            hygiene: HygieneConfig::resolve()?,
            routines: RoutineConfig::resolve()?,
-            sandbox: SandboxModeConfig::resolve()?,
-            claude_code: ClaudeCodeConfig::resolve()?,
+            sandbox: SandboxModeConfig::resolve(settings)?,
+            claude_code: ClaudeCodeConfig::resolve(settings)?,
            skills: SkillsConfig::resolve()?,
            transcription: TranscriptionConfig::resolve(settings)?,
            search: WorkspaceSearchConfig::resolve()?,
@@ -335,52 +331,43 @@ impl Config {
            relay: RelayConfig::from_env(),
        })
    }
+}

-    /// Validate cross-field invariants.
-    ///
-    /// Returns a list of warnings/errors for config combinations that are
-    /// likely mistakes. Called during startup for early feedback.
-    pub fn validate(&self) -> Vec<String> {
-        let mut issues = Vec::new();
+pub(crate) fn load_bootstrap_settings(
+    toml_path: Option<&std::path::Path>,
+) -> Result<Settings, ConfigError> {
+    let _ = dotenvy::dotenv();
+    crate::bootstrap::load_ironclaw_env();

-        // Heartbeat enabled but no workspace path hints
-        if self.heartbeat.enabled && self.database.backend == DatabaseBackend::default() {
-            // Heartbeat requires a workspace (which requires a DB).
-            // This is a soft warning — the system will still start.
-        }
+    let mut settings = Settings::load();
+    Config::apply_toml_overlay(&mut settings, toml_path)?;
+    Ok(settings)
+}

-        // Sandbox enabled but Docker might not be available
-        if self.sandbox.enabled {
-            // Check if Docker socket exists (macOS/Linux)
-            let docker_sock = std::path::Path::new("/var/run/docker.sock");
-            if !docker_sock.exists() {
-                issues.push(
-                    "Sandbox is enabled but /var/run/docker.sock not found. \
-                     Docker may not be running."
-                        .to_string(),
-                );
-            }
-        }
+pub(crate) fn resolve_owner_id(settings: &Settings) -> Result<String, ConfigError> {
+    let env_owner_id = self::helpers::optional_env("IRONCLAW_OWNER_ID")?;
+    let settings_owner_id = settings.owner_id.clone();
+    let configured_owner_id = env_owner_id.clone().or(settings_owner_id.clone());

-        // WASM enabled but tools directory missing
-        if self.wasm.enabled && !self.wasm.tools_dir.exists() {
-            issues.push(format!(
-                "WASM is enabled but tools directory '{}' does not exist",
-                self.wasm.tools_dir.display()
-            ));
-        }
+    let owner_id = configured_owner_id
+        .map(|value| value.trim().to_string())
+        .filter(|value| !value.is_empty())
+        .unwrap_or_else(|| "default".to_string());

-        // Skills enabled but local dir missing
-        if self.skills.enabled && !self.skills.local_dir.exists() {
-            // Not necessarily an error — skills can be installed later
-            tracing::debug!(
-                "Skills enabled but local_dir '{}' does not exist yet",
-                self.skills.local_dir.display()
+    if owner_id == "default"
+        && (env_owner_id.is_some()
+            || settings_owner_id
+                .as_deref()
+                .is_some_and(|value| !value.trim().is_empty()))
+    {
+        WARNED_EXPLICIT_DEFAULT_OWNER_ID.call_once(|| {
+            tracing::warn!(
+                "IRONCLAW_OWNER_ID resolved to the legacy 'default' scope explicitly; durable state will keep legacy owner behavior"
            );
-        }
-
-        issues
+        });
    }
+
+    Ok(owner_id)
 }

 /// Load API keys from the encrypted secrets store into a thread-safe overlay.
@@ -7,7 +7,7 @@ use secrecy::SecretString;
 pub struct RelayConfig {
    /// Base URL of the channel-relay service (e.g., `http://localhost:3001`).
    pub url: String,
-    /// API key for authenticated channel-relay endpoints.
+    /// Bearer token for authenticated channel-relay endpoints (`sk-agent-*`).
    pub api_key: SecretString,
    /// Override for the OAuth callback URL (e.g., a tunnel URL).
    pub callback_url: Option<String>,
@@ -15,12 +15,8 @@ pub struct RelayConfig {
    pub instance_id: Option<String>,
    /// HTTP request timeout in seconds (default: 30).
    pub request_timeout_secs: u64,
-    /// SSE stream long-poll timeout in seconds (default: 86400 = 24 h).
-    pub stream_timeout_secs: u64,
-    /// Initial exponential backoff in milliseconds (default: 1000).
-    pub backoff_initial_ms: u64,
-    /// Maximum exponential backoff in milliseconds (default: 60000).
-    pub backoff_max_ms: u64,
+    /// Path for the webhook callback endpoint (default: `/relay/events`).
+    pub webhook_path: String,
 }

 impl std::fmt::Debug for RelayConfig {
@@ -31,9 +27,7 @@ impl std::fmt::Debug for RelayConfig {
            .field("callback_url", &self.callback_url)
            .field("instance_id", &self.instance_id)
            .field("request_timeout_secs", &self.request_timeout_secs)
-            .field("stream_timeout_secs", &self.stream_timeout_secs)
-            .field("backoff_initial_ms", &self.backoff_initial_ms)
-            .field("backoff_max_ms", &self.backoff_max_ms)
+            .field("webhook_path", &self.webhook_path)
            .finish()
    }
 }
@@ -41,8 +35,10 @@ impl std::fmt::Debug for RelayConfig {
 impl RelayConfig {
    /// Load relay config from environment variables.
    ///
-    /// Returns `None` if either `CHANNEL_RELAY_URL` or `CHANNEL_RELAY_API_KEY`
-    /// is not set, making the relay integration opt-in.
+    /// Returns `None` if either of the required env vars (`CHANNEL_RELAY_URL`,
+    /// `CHANNEL_RELAY_API_KEY`) is not set, making the relay integration opt-in.
+    /// The signing secret is fetched from channel-relay at activation time via
+    /// the authenticated `/relay/signing-secret` endpoint — no env var required.
    pub fn from_env() -> Option<Self> {
        Self::from_env_reader(|key| std::env::var(key).ok())
    }
@@ -55,9 +51,7 @@ impl RelayConfig {
            callback_url: None,
            instance_id: None,
            request_timeout_secs: 30,
-            stream_timeout_secs: 86400,
-            backoff_initial_ms: 1000,
-            backoff_max_ms: 60000,
+            webhook_path: "/relay/events".into(),
        }
    }

@@ -73,15 +67,7 @@ impl RelayConfig {
            request_timeout_secs: env("RELAY_REQUEST_TIMEOUT_SECS")
                .and_then(|v| v.parse().ok())
                .unwrap_or(30),
-            stream_timeout_secs: env("RELAY_STREAM_TIMEOUT_SECS")
-                .and_then(|v| v.parse().ok())
-                .unwrap_or(86400),
-            backoff_initial_ms: env("RELAY_BACKOFF_INITIAL_MS")
-                .and_then(|v| v.parse().ok())
-                .unwrap_or(1000),
-            backoff_max_ms: env("RELAY_BACKOFF_MAX_MS")
-                .and_then(|v| v.parse().ok())
-                .unwrap_or(60000),
+            webhook_path: env("RELAY_WEBHOOK_PATH").unwrap_or_else(|| "/relay/events".into()),
        })
    }
 }
@@ -97,7 +83,21 @@ mod tests {
    }

    #[test]
-    fn from_env_reader_loads_defaults() {
+    fn from_env_reader_requires_only_url_and_api_key() {
+        // Signing secret is fetched at activation time — only URL + API key needed.
+        let config = RelayConfig::from_env_reader(|key| match key {
+            "CHANNEL_RELAY_URL" => Some("http://localhost:3001".into()),
+            "CHANNEL_RELAY_API_KEY" => Some("test-key".into()),
+            _ => None,
+        });
+        assert!(
+            config.is_some(),
+            "relay config should load with just URL + API key"
+        );
+    }
+
+    #[test]
+    fn from_env_reader_loads_all_required() {
        let config = RelayConfig::from_env_reader(|key| match key {
            "CHANNEL_RELAY_URL" => Some("http://localhost:3001".into()),
            "CHANNEL_RELAY_API_KEY" => Some("test-key".into()),
@@ -107,9 +107,7 @@ mod tests {

        assert_eq!(config.url, "http://localhost:3001");
        assert_eq!(config.request_timeout_secs, 30);
-        assert_eq!(config.stream_timeout_secs, 86400);
-        assert_eq!(config.backoff_initial_ms, 1000);
-        assert_eq!(config.backoff_max_ms, 60000);
+        assert_eq!(config.webhook_path, "/relay/events");
        assert!(config.callback_url.is_none());
        assert!(config.instance_id.is_none());
    }
@@ -122,9 +120,7 @@ mod tests {
            "IRONCLAW_OAUTH_CALLBACK_URL" => Some("https://tunnel.example.com".into()),
            "IRONCLAW_INSTANCE_ID" => Some("my-instance".into()),
            "RELAY_REQUEST_TIMEOUT_SECS" => Some("60".into()),
-            "RELAY_STREAM_TIMEOUT_SECS" => Some("43200".into()),
-            "RELAY_BACKOFF_INITIAL_MS" => Some("2000".into()),
-            "RELAY_BACKOFF_MAX_MS" => Some("120000".into()),
+            "RELAY_WEBHOOK_PATH" => Some("/custom/events".into()),
            _ => None,
        })
        .expect("config should be Some");
@@ -135,9 +131,7 @@ mod tests {
        );
        assert_eq!(config.instance_id.as_deref(), Some("my-instance"));
        assert_eq!(config.request_timeout_secs, 60);
-        assert_eq!(config.stream_timeout_secs, 43200);
-        assert_eq!(config.backoff_initial_ms, 2000);
-        assert_eq!(config.backoff_max_ms, 120000);
+        assert_eq!(config.webhook_path, "/custom/events");
    }

    #[test]
@@ -148,7 +142,7 @@ mod tests {
    }

    #[test]
-    fn debug_redacts_api_key() {
+    fn debug_redacts_secrets() {
        let config = RelayConfig::from_values("http://localhost:3001", "super-secret");
        let debug = format!("{:?}", config);
        assert!(debug.contains("[REDACTED]"));
@@ -3,9 +3,48 @@ use crate::error::ConfigError;

 pub use ironclaw_safety::SafetyConfig;

-pub(crate) fn resolve_safety_config() -> Result<SafetyConfig, ConfigError> {
+pub(crate) fn resolve_safety_config(
+    settings: &crate::settings::Settings,
+) -> Result<SafetyConfig, ConfigError> {
+    let ss = &settings.safety;
    Ok(SafetyConfig {
-        max_output_length: parse_optional_env("SAFETY_MAX_OUTPUT_LENGTH", 100_000)?,
-        injection_check_enabled: parse_bool_env("SAFETY_INJECTION_CHECK_ENABLED", true)?,
+        max_output_length: parse_optional_env("SAFETY_MAX_OUTPUT_LENGTH", ss.max_output_length)?,
+        injection_check_enabled: parse_bool_env(
+            "SAFETY_INJECTION_CHECK_ENABLED",
+            ss.injection_check_enabled,
+        )?,
    })
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use crate::config::helpers::ENV_MUTEX;
+    use crate::settings::Settings;
+
+    #[test]
+    fn resolve_falls_back_to_settings() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        let mut settings = Settings::default();
+        settings.safety.max_output_length = 42;
+        settings.safety.injection_check_enabled = false;
+
+        let cfg = resolve_safety_config(&settings).expect("resolve");
+        assert_eq!(cfg.max_output_length, 42);
+        assert!(!cfg.injection_check_enabled);
+    }
+
+    #[test]
+    fn env_overrides_settings() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        let mut settings = Settings::default();
+        settings.safety.max_output_length = 42;
+
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe { std::env::set_var("SAFETY_MAX_OUTPUT_LENGTH", "7") };
+        let cfg = resolve_safety_config(&settings).expect("resolve");
+        unsafe { std::env::remove_var("SAFETY_MAX_OUTPUT_LENGTH") };
+
+        assert_eq!(cfg.max_output_length, 7);
+    }
+}
@@ -52,11 +52,20 @@ impl Default for SandboxModeConfig {
 }

 impl SandboxModeConfig {
-    pub(crate) fn resolve() -> Result<Self, ConfigError> {
+    pub(crate) fn resolve(settings: &crate::settings::Settings) -> Result<Self, ConfigError> {
+        let ss = &settings.sandbox;
+
        let extra_domains = optional_env("SANDBOX_EXTRA_DOMAINS")?
            .map(|s| s.split(',').map(|d| d.trim().to_string()).collect())
-            .unwrap_or_default();
+            .unwrap_or_else(|| {
+                if ss.extra_allowed_domains.is_empty() {
+                    Vec::new()
+                } else {
+                    ss.extra_allowed_domains.clone()
+                }
+            });

+        // reaper/orphan fields have no Settings counterpart — env > default only.
        let reaper_interval_secs: u64 = parse_optional_env("SANDBOX_REAPER_INTERVAL_SECS", 300)?;
        let orphan_threshold_secs: u64 = parse_optional_env("SANDBOX_ORPHAN_THRESHOLD_SECS", 600)?;

@@ -76,14 +85,15 @@ impl SandboxModeConfig {
        }

        Ok(Self {
-            enabled: parse_bool_env("SANDBOX_ENABLED", true)?,
-            policy: parse_string_env("SANDBOX_POLICY", "readonly")?,
+            enabled: parse_bool_env("SANDBOX_ENABLED", ss.enabled)?,
+            policy: parse_string_env("SANDBOX_POLICY", ss.policy.clone())?,
+            // allow_full_access has no Settings counterpart — env > default only.
            allow_full_access: parse_bool_env("SANDBOX_ALLOW_FULL_ACCESS", false)?,
-            timeout_secs: parse_optional_env("SANDBOX_TIMEOUT_SECS", 120)?,
-            memory_limit_mb: parse_optional_env("SANDBOX_MEMORY_LIMIT_MB", 2048)?,
-            cpu_shares: parse_optional_env("SANDBOX_CPU_SHARES", 1024)?,
-            image: parse_string_env("SANDBOX_IMAGE", "ironclaw-worker:latest")?,
-            auto_pull_image: parse_bool_env("SANDBOX_AUTO_PULL", true)?,
+            timeout_secs: parse_optional_env("SANDBOX_TIMEOUT_SECS", ss.timeout_secs)?,
+            memory_limit_mb: parse_optional_env("SANDBOX_MEMORY_LIMIT_MB", ss.memory_limit_mb)?,
+            cpu_shares: parse_optional_env("SANDBOX_CPU_SHARES", ss.cpu_shares)?,
+            image: parse_string_env("SANDBOX_IMAGE", ss.image.clone())?,
+            auto_pull_image: parse_bool_env("SANDBOX_AUTO_PULL", ss.auto_pull_image)?,
            extra_allowed_domains: extra_domains,
            reaper_interval_secs,
            orphan_threshold_secs,
@@ -200,7 +210,7 @@ impl ClaudeCodeConfig {
    /// Load from environment variables only (used inside containers where
    /// there is no database or full config).
    pub fn from_env() -> Self {
-        match Self::resolve() {
+        match Self::resolve_env_only() {
            Ok(c) => c,
            Err(e) => {
                tracing::warn!("Failed to resolve ClaudeCodeConfig: {e}, using defaults");
@@ -253,7 +263,33 @@ impl ClaudeCodeConfig {
        None
    }

-    pub(crate) fn resolve() -> Result<Self, ConfigError> {
+    pub(crate) fn resolve(settings: &crate::settings::Settings) -> Result<Self, ConfigError> {
+        let defaults = Self::default();
+        Ok(Self {
+            // Use settings.sandbox.claude_code_enabled as fallback (written by setup wizard).
+            enabled: parse_bool_env("CLAUDE_CODE_ENABLED", settings.sandbox.claude_code_enabled)?,
+            config_dir: optional_env("CLAUDE_CONFIG_DIR")?
+                .map(std::path::PathBuf::from)
+                .unwrap_or(defaults.config_dir),
+            model: parse_string_env("CLAUDE_CODE_MODEL", defaults.model)?,
+            max_turns: parse_optional_env("CLAUDE_CODE_MAX_TURNS", defaults.max_turns)?,
+            memory_limit_mb: parse_optional_env(
+                "CLAUDE_CODE_MEMORY_LIMIT_MB",
+                defaults.memory_limit_mb,
+            )?,
+            allowed_tools: optional_env("CLAUDE_CODE_ALLOWED_TOOLS")?
+                .map(|s| {
+                    s.split(',')
+                        .map(|t| t.trim().to_string())
+                        .filter(|t| !t.is_empty())
+                        .collect()
+                })
+                .unwrap_or(defaults.allowed_tools),
+        })
+    }
+
+    /// Resolve from env vars only, no Settings. Used inside containers.
+    fn resolve_env_only() -> Result<Self, ConfigError> {
        let defaults = Self::default();
        Ok(Self {
            enabled: parse_bool_env("CLAUDE_CODE_ENABLED", defaults.enabled)?,
@@ -554,6 +590,80 @@ mod tests {
        );
    }

+    // ── Settings fallback tests ──────────────────────────────────────
+
+    #[test]
+    fn sandbox_resolve_falls_back_to_settings() {
+        let _guard = crate::config::helpers::ENV_MUTEX
+            .lock()
+            .expect("env mutex poisoned");
+        let mut settings = crate::settings::Settings::default();
+        settings.sandbox.cpu_shares = 99;
+        settings.sandbox.auto_pull_image = false;
+        settings.sandbox.enabled = false;
+
+        let cfg = SandboxModeConfig::resolve(&settings).expect("resolve");
+        assert!(!cfg.enabled);
+        assert_eq!(cfg.cpu_shares, 99);
+        assert!(!cfg.auto_pull_image);
+    }
+
+    #[test]
+    fn sandbox_env_overrides_settings() {
+        let _guard = crate::config::helpers::ENV_MUTEX
+            .lock()
+            .expect("env mutex poisoned");
+        let mut settings = crate::settings::Settings::default();
+        settings.sandbox.timeout_secs = 999;
+
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe { std::env::set_var("SANDBOX_TIMEOUT_SECS", "5") };
+        let cfg = SandboxModeConfig::resolve(&settings).expect("resolve");
+        unsafe { std::env::remove_var("SANDBOX_TIMEOUT_SECS") };
+
+        assert_eq!(cfg.timeout_secs, 5);
+    }
+
+    // ── ClaudeCodeConfig settings fallback tests ────────────────────
+
+    #[test]
+    fn claude_code_resolve_uses_settings_enabled() {
+        let _guard = crate::config::helpers::ENV_MUTEX
+            .lock()
+            .expect("env mutex poisoned");
+        let mut settings = crate::settings::Settings::default();
+        settings.sandbox.claude_code_enabled = true;
+
+        let cfg = ClaudeCodeConfig::resolve(&settings).expect("resolve");
+        assert!(cfg.enabled);
+    }
+
+    #[test]
+    fn claude_code_resolve_defaults_disabled() {
+        let _guard = crate::config::helpers::ENV_MUTEX
+            .lock()
+            .expect("env mutex poisoned");
+        let settings = crate::settings::Settings::default();
+        let cfg = ClaudeCodeConfig::resolve(&settings).expect("resolve");
+        assert!(!cfg.enabled);
+    }
+
+    #[test]
+    fn claude_code_env_overrides_settings() {
+        let _guard = crate::config::helpers::ENV_MUTEX
+            .lock()
+            .expect("env mutex poisoned");
+        let mut settings = crate::settings::Settings::default();
+        settings.sandbox.claude_code_enabled = true;
+
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe { std::env::set_var("CLAUDE_CODE_ENABLED", "false") };
+        let cfg = ClaudeCodeConfig::resolve(&settings).expect("resolve");
+        unsafe { std::env::remove_var("CLAUDE_CODE_ENABLED") };
+
+        assert!(!cfg.enabled);
+    }
+
    #[test]
    fn test_readonly_policy_unaffected() {
        let config = SandboxModeConfig {
@@ -9,11 +9,15 @@ use crate::settings::Settings;
 pub struct TranscriptionConfig {
    /// Whether audio transcription is enabled.
    pub enabled: bool,
-    /// Provider: "openai" (default).
+    /// Provider: "openai" (default) or "chat_completions".
    pub provider: String,
    /// OpenAI API key (reuses OPENAI_API_KEY).
    pub openai_api_key: Option<SecretString>,
-    /// Model to use (default: "whisper-1").
+    /// Explicit transcription API key (overrides provider-specific keys).
+    pub api_key: Option<SecretString>,
+    /// LLM API key (reuses LLM_API_KEY, used as fallback for chat_completions).
+    pub llm_api_key: Option<SecretString>,
+    /// Model to use (default depends on provider).
    pub model: String,
    /// Base URL override for the transcription API.
    pub base_url: Option<String>,
@@ -25,6 +29,8 @@ impl Default for TranscriptionConfig {
            enabled: false,
            provider: "openai".to_string(),
            openai_api_key: None,
+            api_key: None,
+            llm_api_key: None,
            model: "whisper-1".to_string(),
            base_url: None,
        }
@@ -42,8 +48,15 @@ impl TranscriptionConfig {
            optional_env("TRANSCRIPTION_PROVIDER")?.unwrap_or_else(|| "openai".to_string());

        let openai_api_key = optional_env("OPENAI_API_KEY")?.map(SecretString::from);
+        let api_key = optional_env("TRANSCRIPTION_API_KEY")?.map(SecretString::from);
+        let llm_api_key = optional_env("LLM_API_KEY")?.map(SecretString::from);

-        let model = optional_env("TRANSCRIPTION_MODEL")?.unwrap_or_else(|| "whisper-1".to_string());
+        let default_model = match provider.as_str() {
+            "chat_completions" => "google/gemini-2.0-flash-001",
+            _ => "whisper-1",
+        };
+        let model =
+            optional_env("TRANSCRIPTION_MODEL")?.unwrap_or_else(|| default_model.to_string());

        let base_url = optional_env("TRANSCRIPTION_BASE_URL")?;

@@ -51,29 +64,67 @@ impl TranscriptionConfig {
            enabled,
            provider,
            openai_api_key,
+            api_key,
+            llm_api_key,
            model,
            base_url,
        })
    }

+    /// Resolve the API key for the configured provider.
+    ///
+    /// Priority: `TRANSCRIPTION_API_KEY` > provider-specific key.
+    fn resolve_api_key(&self) -> Option<&SecretString> {
+        self.api_key
+            .as_ref()
+            .or_else(|| match self.provider.as_str() {
+                "chat_completions" => self.llm_api_key.as_ref().or(self.openai_api_key.as_ref()),
+                _ => self.openai_api_key.as_ref(),
+            })
+    }
+
    /// Create the transcription provider if enabled and configured.
    pub fn create_provider(&self) -> Option<Box<dyn crate::transcription::TranscriptionProvider>> {
        if !self.enabled {
            return None;
        }

-        // Currently only OpenAI Whisper is supported; more providers can be
-        // added here with a match on self.provider.
-        let api_key = self.openai_api_key.as_ref()?;
-        tracing::info!(model = %self.model, "Audio transcription enabled via OpenAI Whisper");
+        let api_key = self.resolve_api_key()?;

-        let mut provider = crate::transcription::OpenAiWhisperProvider::new(api_key.clone())
-            .with_model(&self.model);
+        match self.provider.as_str() {
+            "chat_completions" => {
+                tracing::info!(
+                    model = %self.model,
+                    "Audio transcription enabled via Chat Completions API"
+                );

-        if let Some(ref base_url) = self.base_url {
-            provider = provider.with_base_url(base_url);
+                let mut provider = crate::transcription::ChatCompletionsTranscriptionProvider::new(
+                    api_key.clone(),
+                )
+                .with_model(&self.model);
+
+                if let Some(ref base_url) = self.base_url {
+                    provider = provider.with_base_url(base_url);
+                }
+
+                Some(Box::new(provider))
+            }
+            _ => {
+                tracing::info!(
+                    model = %self.model,
+                    "Audio transcription enabled via OpenAI Whisper"
+                );
+
+                let mut provider =
+                    crate::transcription::OpenAiWhisperProvider::new(api_key.clone())
+                        .with_model(&self.model);
+
+                if let Some(ref base_url) = self.base_url {
+                    provider = provider.with_base_url(base_url);
+                }
+
+                Some(Box::new(provider))
+            }
        }
-
-        Some(Box::new(provider))
    }
 }
@@ -44,20 +44,30 @@ fn default_tools_dir() -> PathBuf {
 }

 impl WasmConfig {
-    pub(crate) fn resolve() -> Result<Self, ConfigError> {
+    pub(crate) fn resolve(settings: &crate::settings::Settings) -> Result<Self, ConfigError> {
+        let ws = &settings.wasm;
        Ok(Self {
-            enabled: parse_bool_env("WASM_ENABLED", true)?,
+            enabled: parse_bool_env("WASM_ENABLED", ws.enabled)?,
            tools_dir: optional_env("WASM_TOOLS_DIR")?
                .map(PathBuf::from)
+                .or_else(|| ws.tools_dir.clone())
                .unwrap_or_else(default_tools_dir),
            default_memory_limit: parse_optional_env(
                "WASM_DEFAULT_MEMORY_LIMIT",
-                10 * 1024 * 1024,
+                ws.default_memory_limit,
            )?,
-            default_timeout_secs: parse_optional_env("WASM_DEFAULT_TIMEOUT_SECS", 60)?,
-            default_fuel_limit: parse_optional_env("WASM_DEFAULT_FUEL_LIMIT", 10_000_000)?,
-            cache_compiled: parse_bool_env("WASM_CACHE_COMPILED", true)?,
-            cache_dir: optional_env("WASM_CACHE_DIR")?.map(PathBuf::from),
+            default_timeout_secs: parse_optional_env(
+                "WASM_DEFAULT_TIMEOUT_SECS",
+                ws.default_timeout_secs,
+            )?,
+            default_fuel_limit: parse_optional_env(
+                "WASM_DEFAULT_FUEL_LIMIT",
+                ws.default_fuel_limit,
+            )?,
+            cache_compiled: parse_bool_env("WASM_CACHE_COMPILED", ws.cache_compiled)?,
+            cache_dir: optional_env("WASM_CACHE_DIR")?
+                .map(PathBuf::from)
+                .or_else(|| ws.cache_dir.clone()),
        })
    }

@@ -81,3 +91,36 @@ impl WasmConfig {
        }
    }
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use crate::config::helpers::ENV_MUTEX;
+    use crate::settings::Settings;
+
+    #[test]
+    fn resolve_falls_back_to_settings() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        let mut settings = Settings::default();
+        settings.wasm.default_memory_limit = 42;
+        settings.wasm.cache_compiled = false;
+
+        let cfg = WasmConfig::resolve(&settings).expect("resolve");
+        assert_eq!(cfg.default_memory_limit, 42);
+        assert!(!cfg.cache_compiled);
+    }
+
+    #[test]
+    fn env_overrides_settings() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        let mut settings = Settings::default();
+        settings.wasm.default_fuel_limit = 42;
+
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe { std::env::set_var("WASM_DEFAULT_FUEL_LIMIT", "7") };
+        let cfg = WasmConfig::resolve(&settings).expect("resolve");
+        unsafe { std::env::remove_var("WASM_DEFAULT_FUEL_LIMIT") };
+
+        assert_eq!(cfg.default_fuel_limit, 7);
+    }
+}
@@ -0,0 +1,319 @@
+//! Structured fallback deliverables for failed or stuck jobs.
+//!
+//! When a job fails or is detected as stuck, a [`FallbackDeliverable`] captures
+//! what was accomplished before the failure: partial results, action statistics,
+//! cost, and timing. This gives users visibility into terminal jobs instead of
+//! just an error string.
+//!
+//! Fallback deliverables are stored in `JobContext.metadata["fallback_deliverable"]`
+//! and surfaced through the `job_status` tool.
+
+use serde::{Deserialize, Serialize};
+
+use crate::context::memory::Memory;
+use crate::context::state::JobContext;
+
+/// Structured summary of a failed or stuck job.
+///
+/// Stored in `JobContext.metadata["fallback_deliverable"]` when a job fails
+/// or is marked stuck. Surfaced through the `job_status` tool.
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct FallbackDeliverable {
+    /// True if at least one action succeeded before failure.
+    pub partial: bool,
+    /// Why the job failed.
+    pub failure_reason: String,
+    /// Last action taken before failure.
+    pub last_action: Option<LastAction>,
+    /// Aggregate action statistics.
+    pub action_stats: ActionStats,
+    /// Total tokens consumed.
+    pub tokens_used: u64,
+    /// Total cost incurred (decimal as string for JSON safety).
+    pub cost: String,
+    /// Wall-clock elapsed time in seconds.
+    pub elapsed_secs: f64,
+    /// Number of self-repair attempts.
+    pub repair_attempts: u32,
+}
+
+/// Summary of the last action taken before failure.
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct LastAction {
+    pub tool_name: String,
+    /// Truncated to 200 bytes (UTF-8 safe).
+    pub output_preview: String,
+    pub success: bool,
+}
+
+/// Aggregate action counts.
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct ActionStats {
+    pub total: u32,
+    pub successful: u32,
+    pub failed: u32,
+}
+
+impl FallbackDeliverable {
+    /// Build a fallback deliverable from a job context and its memory.
+    pub fn build(ctx: &JobContext, memory: &Memory, reason: &str) -> Self {
+        let successful = memory.successful_actions() as u32;
+        let failed = memory.failed_actions() as u32;
+        let total = memory.actions.len() as u32;
+
+        let last_action = memory.last_action().map(|a| {
+            // Use sanitized output to avoid leaking secrets through the fallback API surface.
+            // For failed actions (no sanitized output), fall back to the error message.
+            // Borrow the string slice directly when possible to avoid cloning
+            // potentially large outputs just for truncation.
+            let owned_fallback;
+            let preview_str: &str = if let Some(v) = a.output_sanitized.as_ref() {
+                match v {
+                    serde_json::Value::String(s) => s.as_str(),
+                    other => {
+                        owned_fallback = serde_json::to_string(other).unwrap_or_default();
+                        &owned_fallback
+                    }
+                }
+            } else if let Some(ref err) = a.error {
+                err.as_str()
+            } else {
+                ""
+            };
+            let preview = truncate_str(preview_str, 200);
+            LastAction {
+                tool_name: a.tool_name.clone(),
+                output_preview: preview.to_string(),
+                success: a.success,
+            }
+        });
+
+        let elapsed_secs = ctx.elapsed().map_or(0.0, |d| d.as_secs_f64());
+
+        Self {
+            partial: successful > 0,
+            failure_reason: truncate_str(reason, 1000).to_string(),
+            last_action,
+            action_stats: ActionStats {
+                total,
+                successful,
+                failed,
+            },
+            tokens_used: ctx.total_tokens_used,
+            cost: ctx.actual_cost.to_string(),
+            elapsed_secs,
+            repair_attempts: ctx.repair_attempts,
+        }
+    }
+}
+
+/// Truncate a string to at most `max_len` bytes on a char boundary.
+fn truncate_str(s: &str, max_len: usize) -> &str {
+    &s[..crate::util::floor_char_boundary(s, max_len)]
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use crate::context::memory::Memory;
+    use crate::context::state::JobContext;
+    use chrono::{Duration, Utc};
+    use rust_decimal::Decimal;
+    use std::time::Duration as StdDuration;
+
+    #[test]
+    fn test_fallback_zero_actions() {
+        let ctx = JobContext::new("Test", "Empty job");
+        let memory = Memory::new(ctx.job_id);
+
+        let fb = FallbackDeliverable::build(&ctx, &memory, "timed out");
+
+        assert!(!fb.partial); // safety: test
+        assert_eq!(fb.failure_reason, "timed out"); // safety: test
+        assert!(fb.last_action.is_none()); // safety: test
+        assert_eq!(fb.action_stats.total, 0); // safety: test
+        assert_eq!(fb.action_stats.successful, 0); // safety: test
+        assert_eq!(fb.action_stats.failed, 0); // safety: test
+        assert_eq!(fb.tokens_used, 0); // safety: test
+        assert_eq!(fb.cost, "0"); // safety: test
+        assert_eq!(fb.repair_attempts, 0); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_mixed_actions() {
+        let mut ctx = JobContext::new("Test", "Mixed job");
+        ctx.total_tokens_used = 5000;
+        ctx.actual_cost = Decimal::new(42, 2); // 0.42
+        ctx.repair_attempts = 1;
+
+        let mut memory = Memory::new(ctx.job_id);
+
+        // 3 successes
+        for _ in 0..3 {
+            let action = memory
+                .create_action("tool_a", serde_json::json!({}))
+                .succeed(
+                    Some("output".to_string()),
+                    serde_json::json!({}),
+                    StdDuration::from_secs(1),
+                );
+            memory.record_action(action);
+        }
+        // 2 failures
+        for _ in 0..2 {
+            let action = memory
+                .create_action("tool_b", serde_json::json!({}))
+                .fail("broke", StdDuration::from_secs(1));
+            memory.record_action(action);
+        }
+
+        let fb = FallbackDeliverable::build(&ctx, &memory, "max iterations");
+
+        assert!(fb.partial); // safety: test
+        assert_eq!(fb.action_stats.total, 5); // safety: test
+        assert_eq!(fb.action_stats.successful, 3); // safety: test
+        assert_eq!(fb.action_stats.failed, 2); // safety: test
+        assert_eq!(fb.tokens_used, 5000); // safety: test
+        assert_eq!(fb.cost, "0.42"); // safety: test
+        assert_eq!(fb.repair_attempts, 1); // safety: test
+        assert!(fb.last_action.is_some()); // safety: test
+        let la = fb.last_action.unwrap(); // safety: test
+        assert_eq!(la.tool_name, "tool_b"); // safety: test
+        assert!(!la.success); // safety: test
+        // Failed actions should surface the error message as the output preview
+        assert_eq!(la.output_preview, "broke"); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_failed_action_shows_error() {
+        let ctx = JobContext::new("Test", "Error preview");
+        let mut memory = Memory::new(ctx.job_id);
+
+        let action = memory
+            .create_action("broken_tool", serde_json::json!({}))
+            .fail("connection timed out after 30s", StdDuration::from_secs(30));
+        memory.record_action(action);
+
+        let fb = FallbackDeliverable::build(&ctx, &memory, "tool failure");
+        let la = fb.last_action.unwrap(); // safety: test
+        assert!(!la.success); // safety: test
+        assert_eq!(la.output_preview, "connection timed out after 30s"); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_last_action_truncation() {
+        let ctx = JobContext::new("Test", "Truncation");
+        let mut memory = Memory::new(ctx.job_id);
+
+        let long_output = "x".repeat(500);
+        let action = memory
+            .create_action("tool_c", serde_json::json!({}))
+            .succeed(
+                Some(long_output.clone()),
+                serde_json::Value::String(long_output),
+                StdDuration::from_secs(1),
+            );
+        memory.record_action(action);
+
+        let fb = FallbackDeliverable::build(&ctx, &memory, "failed");
+        let la = fb.last_action.unwrap(); // safety: test
+        assert!(la.output_preview.len() <= 200); // safety: test
+        assert!(!la.output_preview.is_empty()); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_uses_sanitized_output() {
+        let ctx = JobContext::new("Test", "Sanitized");
+        let mut memory = Memory::new(ctx.job_id);
+
+        let action = memory
+            .create_action("tool_d", serde_json::json!({}))
+            .succeed(
+                Some("[REDACTED]".to_string()),
+                serde_json::json!({"api_key": "sk-secret-key-12345"}),
+                StdDuration::from_secs(1),
+            );
+        memory.record_action(action);
+
+        let fb = FallbackDeliverable::build(&ctx, &memory, "failed");
+        let la = fb.last_action.unwrap(); // safety: test
+        // Must use sanitized output, not raw
+        assert!(!la.output_preview.contains("sk-secret")); // safety: test
+        assert!(la.output_preview.contains("REDACTED")); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_elapsed_time() {
+        let mut ctx = JobContext::new("Test", "Timing");
+        let now = Utc::now();
+        ctx.started_at = Some(now - Duration::seconds(10));
+        ctx.completed_at = Some(now);
+
+        let memory = Memory::new(ctx.job_id);
+        let fb = FallbackDeliverable::build(&ctx, &memory, "failed");
+
+        // Should be approximately 10 seconds
+        assert!((fb.elapsed_secs - 10.0).abs() < 0.1); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_no_started_at() {
+        let ctx = JobContext::new("Test", "Never started");
+        let memory = Memory::new(ctx.job_id);
+
+        let fb = FallbackDeliverable::build(&ctx, &memory, "failed");
+        assert!((fb.elapsed_secs - 0.0).abs() < 0.001); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_elapsed_time_no_completed_at() {
+        let mut ctx = JobContext::new("Test", "Still running");
+        ctx.started_at = Some(Utc::now() - Duration::seconds(5));
+        // completed_at is None — should use Utc::now() as fallback
+
+        let memory = Memory::new(ctx.job_id);
+        let fb = FallbackDeliverable::build(&ctx, &memory, "stuck");
+
+        // Should be approximately 5 seconds (using now as end time)
+        assert!(fb.elapsed_secs >= 4.0 && fb.elapsed_secs <= 7.0); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_failure_reason_truncation() {
+        let ctx = JobContext::new("Test", "Long reason");
+        let memory = Memory::new(ctx.job_id);
+
+        let long_reason = "x".repeat(5000);
+        let fb = FallbackDeliverable::build(&ctx, &memory, &long_reason);
+
+        assert!(fb.failure_reason.len() <= 1000); // safety: test
+        assert!(!fb.failure_reason.is_empty()); // safety: test
+    }
+
+    #[test]
+    fn test_truncate_str_ascii() {
+        assert_eq!(truncate_str("hello", 10), "hello"); // safety: test
+        assert_eq!(truncate_str("hello world", 5), "hello"); // safety: test
+    }
+
+    #[test]
+    fn test_truncate_str_unicode() {
+        // "é" is 2 bytes in UTF-8
+        let s = "café";
+        assert_eq!(truncate_str(s, 10), "café"); // safety: test
+        // Truncating at 4 would split "é", should back up to 3
+        assert_eq!(truncate_str(s, 4), "caf"); // safety: test
+    }
+
+    #[test]
+    fn test_fallback_serialization() {
+        let ctx = JobContext::new("Test", "Serialize");
+        let memory = Memory::new(ctx.job_id);
+        let fb = FallbackDeliverable::build(&ctx, &memory, "test error");
+
+        // Should serialize to JSON and back without error
+        let json = serde_json::to_value(&fb).unwrap(); // safety: test
+        let deserialized: FallbackDeliverable = serde_json::from_value(json).unwrap(); // safety: test
+        assert_eq!(deserialized.failure_reason, "test error"); // safety: test
+    }
+}
@@ -46,11 +46,17 @@ impl ContextManager {
        description: impl Into<String>,
    ) -> Result<Uuid, JobError> {
        // Hold write lock for the entire check-insert to prevent TOCTOU races
-        // where two concurrent calls both pass the active_count check.
+        // where two concurrent calls both pass the parallel_count check.
        let mut contexts = self.contexts.write().await;
-        let active_count = contexts.values().filter(|c| c.state.is_active()).count();
+        // Only count jobs that consume execution slots (Pending, InProgress, Stuck).
+        // Completed and Submitted jobs are no longer actively executing and shouldn't
+        // block new job creation.
+        let parallel_count = contexts
+            .values()
+            .filter(|c| c.state.is_parallel_blocking())
+            .count();

-        if active_count >= self.max_jobs {
+        if parallel_count >= self.max_jobs {
            return Err(JobError::MaxJobsExceeded { max: self.max_jobs });
        }

@@ -965,4 +971,218 @@ mod tests {
        // And it's in the initial state (Pending), not modified by concurrent workers
        assert_eq!(returned_ctx.state, crate::context::JobState::Pending); // safety: test code
    }
+
+    #[tokio::test]
+    async fn sequential_routines_unlimited_completed_not_counted() {
+        // TEST: Sequential (non-parallel) routines should NOT be limited by max_jobs.
+        //
+        // Completed/Submitted jobs should NOT count toward the parallel job limit,
+        // since they're no longer actively consuming execution resources.
+        //
+        // Scenario: Create 10 sequential routines, each completing before the next starts.
+        // Currently FAILS because Completed jobs still count as "active".
+        // After fix, should PASS because only Pending/InProgress/Stuck count.
+
+        let manager = ContextManager::new(5); // max 5 truly parallel jobs
+
+        // Try to create and complete 10 sequential routines
+        for i in 0..10 {
+            let result = manager
+                .create_job(format!("Sequential Routine {}", i), "one at a time")
+                .await;
+
+            match result {
+                Ok(job_id) => {
+                    // Simulate execution: Pending -> InProgress -> Completed
+                    manager
+                        .update_context(job_id, |ctx| {
+                            ctx.transition_to(crate::context::JobState::InProgress, None)
+                        })
+                        .await
+                        .unwrap()
+                        .unwrap();
+
+                    manager
+                        .update_context(job_id, |ctx| {
+                            ctx.transition_to(crate::context::JobState::Completed, None)
+                        })
+                        .await
+                        .unwrap()
+                        .unwrap();
+
+                    println!("✓ Routine {} created and completed", i);
+                }
+                Err(JobError::MaxJobsExceeded { max }) => {
+                    panic!(
+                        "✗ Routine {} FAILED to create: MaxJobsExceeded (max={}).\n\
+                         This shows the bug: Completed jobs from routines 0-4 are still counting \
+                         toward the limit even though they're not running.\n\
+                         After the fix, this test should pass because Completed jobs won't count.",
+                        i, max
+                    );
+                }
+                Err(e) => {
+                    panic!("Unexpected error for routine {}: {:?}", i, e);
+                }
+            }
+        }
+
+        // If we reach here, all 10 routines succeeded (bug is fixed)
+        assert_eq!(manager.all_jobs().await.len(), 10);
+        println!("✓ SUCCESS: All 10 sequential routines created despite max_jobs=5 limit");
+        println!("  This is correct: Completed jobs don't count toward parallel limit");
+    }
+
+    #[tokio::test]
+    async fn parallel_jobs_limit_enforced_for_active_jobs() {
+        // TEST: Parallel (simultaneous) jobs ARE limited by max_jobs.
+        //
+        // Jobs in Pending/InProgress/Stuck states consume execution slots.
+        // The 6th truly-active job should fail because the limit is 5.
+        //
+        // This test verifies the limit DOES work correctly for parallel execution.
+
+        let manager = ContextManager::new(5); // max 5 parallel jobs
+
+        // Create 5 jobs and make them InProgress (simulating parallel execution)
+        let mut job_ids = Vec::new();
+        for i in 0..5 {
+            let job_id = manager
+                .create_job(format!("Parallel Job {}", i), "running in parallel")
+                .await
+                .expect("First 5 jobs should create successfully");
+            job_ids.push(job_id);
+
+            // Transition to InProgress (simulating active execution)
+            manager
+                .update_context(job_id, |ctx| {
+                    ctx.transition_to(crate::context::JobState::InProgress, None)
+                })
+                .await
+                .unwrap()
+                .unwrap();
+        }
+
+        // Verify all 5 jobs are InProgress
+        for job_id in &job_ids {
+            let ctx = manager.get_context(*job_id).await.unwrap();
+            assert_eq!(
+                ctx.state,
+                crate::context::JobState::InProgress,
+                "All jobs should be InProgress"
+            );
+        }
+
+        // Check active count - should be 5 (all InProgress)
+        let active_count = manager.active_count().await;
+        assert_eq!(
+            active_count, 5,
+            "Active count should be 5 (all InProgress jobs count)"
+        );
+
+        // Try to create a 6th job - should FAIL because limit is reached
+        let result = manager.create_job("Parallel Job 6", "sixth job").await;
+
+        match result {
+            Err(JobError::MaxJobsExceeded { max: 5 }) => {
+                println!("✓ SUCCESS: Parallel job limit correctly enforced at 5 active jobs");
+                println!("✓ 6th InProgress job correctly blocked when 5 are already running");
+            }
+            Ok(_) => {
+                panic!(
+                    "FAILED: 6th parallel job should have been blocked \
+                     but was created. Limit enforcement is broken."
+                );
+            }
+            Err(e) => {
+                panic!(
+                    "UNEXPECTED ERROR: Expected MaxJobsExceeded but got: {:?}",
+                    e
+                );
+            }
+        }
+    }
+
+    #[tokio::test]
+    async fn completed_jobs_should_free_slots_after_fix() {
+        // TEST: After the fix, Completed jobs should NOT count toward the limit.
+        //
+        // This test demonstrates that when a job transitions from InProgress -> Completed,
+        // it should free up a slot in the parallel execution limit.
+        //
+        // Currently FAILS (bug not fixed), proving Completed jobs incorrectly stay in the limit.
+        // After fix, this will PASS (Completed jobs freed their slot).
+
+        let manager = ContextManager::new(5); // max 5 parallel jobs
+
+        // Create 5 InProgress jobs (fill the limit)
+        let mut job_ids = Vec::new();
+        for i in 0..5 {
+            let job_id = manager
+                .create_job(format!("Job {}", i), "parallel")
+                .await
+                .unwrap();
+            job_ids.push(job_id);
+
+            manager
+                .update_context(job_id, |ctx| {
+                    ctx.transition_to(crate::context::JobState::InProgress, None)
+                })
+                .await
+                .unwrap()
+                .unwrap();
+        }
+
+        // Verify limit is hit
+        let result = manager.create_job("Job 5", "should fail").await;
+        assert!(
+            matches!(result, Err(JobError::MaxJobsExceeded { max: 5 })),
+            "Limit should be hit with 5 InProgress jobs"
+        );
+        println!("✓ Limit enforced: 5 InProgress jobs block 6th creation");
+
+        // Now transition job 0 from InProgress -> Completed
+        manager
+            .update_context(job_ids[0], |ctx| {
+                ctx.transition_to(crate::context::JobState::Completed, None)
+            })
+            .await
+            .unwrap()
+            .unwrap();
+
+        println!("✓ Job 0 transitioned: InProgress -> Completed");
+
+        // Try to create a 6th job - this will FAIL until the bug is fixed
+        let result = manager
+            .create_job("Job 5 (retry)", "after 1 Completed")
+            .await;
+
+        match result {
+            Ok(job_6) => {
+                println!("✓ SUCCESS: 6th job created after job 0 completed");
+                println!("✓ This proves Completed jobs don't count toward the limit (BUG FIXED)");
+
+                // Verify we can transition it to InProgress
+                manager
+                    .update_context(job_6, |ctx| {
+                        ctx.transition_to(crate::context::JobState::InProgress, None)
+                    })
+                    .await
+                    .unwrap()
+                    .unwrap();
+                println!("✓ 6th job now InProgress: 4 remaining + 1 new = 5 limit reached");
+            }
+            Err(JobError::MaxJobsExceeded { max: 5 }) => {
+                panic!(
+                    "✗ BUG NOT FIXED: 6th job creation still blocked after freeing slot.\n\
+                     State: 1 Completed (job 0) + 4 InProgress (jobs 1-4) = 5 active\n\
+                     BUG: Completed job 0 still counts toward limit\n\
+                     EXPECTED: Only 4 InProgress count, 1 slot free"
+                );
+            }
+            Err(e) => {
+                panic!("Unexpected error: {:?}", e);
+            }
+        }
+    }
 }
@@ -58,15 +58,19 @@ impl ActionRecord {
    }

    /// Mark the action as successful.
+    ///
+    /// `output_sanitized` is the tool output after safety processing (string).
+    /// `output_raw` is the original tool result (JSON value, stored as a
+    /// pretty-printed JSON string in `ActionRecord.output_raw`).
    pub fn succeed(
        mut self,
-        output_raw: Option<String>,
-        output_sanitized: serde_json::Value,
+        output_sanitized: Option<String>,
+        output_raw: serde_json::Value,
        duration: Duration,
    ) -> Self {
        self.success = true;
-        self.output_raw = output_raw;
-        self.output_sanitized = Some(output_sanitized);
+        self.output_raw = Some(serde_json::to_string_pretty(&output_raw).unwrap_or_default());
+        self.output_sanitized = output_sanitized.map(serde_json::Value::String);
        self.duration = duration;
        self
    }
@@ -248,15 +252,15 @@ mod tests {
    #[test]
    fn test_action_record() {
        let action = ActionRecord::new(0, "test", serde_json::json!({"key": "value"}));
-        assert_eq!(action.sequence, 0);
-        assert!(!action.success);
+        assert_eq!(action.sequence, 0); // safety: test
+        assert!(!action.success); // safety: test

        let action = action.succeed(
            Some("raw".to_string()),
            serde_json::json!({"result": "ok"}),
            Duration::from_millis(100),
        );
-        assert!(action.success);
+        assert!(action.success); // safety: test
    }

    #[test]
@@ -267,7 +271,7 @@ mod tests {
        memory.add(ChatMessage::user("How are you?"));
        memory.add(ChatMessage::assistant("Good!"));

-        assert_eq!(memory.len(), 3); // Oldest removed
+        assert_eq!(memory.len(), 3); // Oldest removed // safety: test
    }

    #[test]
@@ -286,9 +290,9 @@ mod tests {
            .with_cost(Decimal::new(20, 1));
        memory.record_action(action2);

-        assert_eq!(memory.total_cost(), Decimal::new(30, 1));
-        assert_eq!(memory.total_duration(), Duration::from_secs(3));
-        assert_eq!(memory.successful_actions(), 2);
+        assert_eq!(memory.total_cost(), Decimal::new(30, 1)); // safety: test
+        assert_eq!(memory.total_duration(), Duration::from_secs(3)); // safety: test
+        assert_eq!(memory.successful_actions(), 2); // safety: test
    }

    #[test]
@@ -296,11 +300,11 @@ mod tests {
        let action = ActionRecord::new(1, "broken_tool", serde_json::json!({"x": 1}));
        let action = action.fail("something went wrong", Duration::from_millis(50));

-        assert!(!action.success);
-        assert_eq!(action.error.as_deref(), Some("something went wrong"));
-        assert_eq!(action.duration, Duration::from_millis(50));
-        assert!(action.output_raw.is_none());
-        assert!(action.output_sanitized.is_none());
+        assert!(!action.success); // safety: test
+        assert_eq!(action.error.as_deref(), Some("something went wrong")); // safety: test
+        assert_eq!(action.duration, Duration::from_millis(50)); // safety: test
+        assert!(action.output_raw.is_none()); // safety: test
+        assert!(action.output_sanitized.is_none()); // safety: test
    }

    #[test]
@@ -308,9 +312,9 @@ mod tests {
        let action = ActionRecord::new(0, "risky_tool", serde_json::json!({}));
        let action = action.with_warnings(vec!["suspicious pattern".into(), "possible xss".into()]);

-        assert_eq!(action.sanitization_warnings.len(), 2);
-        assert_eq!(action.sanitization_warnings[0], "suspicious pattern");
-        assert_eq!(action.sanitization_warnings[1], "possible xss");
+        assert_eq!(action.sanitization_warnings.len(), 2); // safety: test
+        assert_eq!(action.sanitization_warnings[0], "suspicious pattern"); // safety: test
+        assert_eq!(action.sanitization_warnings[1], "possible xss"); // safety: test
    }

    #[test]
@@ -319,41 +323,46 @@ mod tests {
        let cost = Decimal::new(42, 2); // 0.42
        let action = action.with_cost(cost);

-        assert_eq!(action.cost, Some(Decimal::new(42, 2)));
+        assert_eq!(action.cost, Some(Decimal::new(42, 2))); // safety: test
    }

    #[test]
    fn test_action_record_new_defaults() {
        let action = ActionRecord::new(5, "my_tool", serde_json::json!({"key": "val"}));

-        assert_eq!(action.sequence, 5);
-        assert_eq!(action.tool_name, "my_tool");
-        assert_eq!(action.input, serde_json::json!({"key": "val"}));
-        assert!(!action.success);
-        assert!(action.output_raw.is_none());
-        assert!(action.output_sanitized.is_none());
-        assert!(action.sanitization_warnings.is_empty());
-        assert!(action.cost.is_none());
-        assert_eq!(action.duration, Duration::ZERO);
-        assert!(action.error.is_none());
+        assert_eq!(action.sequence, 5); // safety: test
+        assert_eq!(action.tool_name, "my_tool"); // safety: test
+        assert_eq!(action.input, serde_json::json!({"key": "val"})); // safety: test
+        assert!(!action.success); // safety: test
+        assert!(action.output_raw.is_none()); // safety: test
+        assert!(action.output_sanitized.is_none()); // safety: test
+        assert!(action.sanitization_warnings.is_empty()); // safety: test
+        assert!(action.cost.is_none()); // safety: test
+        assert_eq!(action.duration, Duration::ZERO); // safety: test
+        assert!(action.error.is_none()); // safety: test
    }

    #[test]
    fn test_action_record_succeed_sets_fields() {
        let action = ActionRecord::new(0, "tool", serde_json::json!({}));
        let action = action.succeed(
-            Some("raw output here".into()),
+            Some("sanitized output".into()),
            serde_json::json!({"clean": true}),
            Duration::from_secs(7),
        );

-        assert!(action.success);
-        assert_eq!(action.output_raw.as_deref(), Some("raw output here"));
+        assert!(action.success); // safety: test
+        // output_raw is the JSON value pretty-printed
+        let expected_raw =
+            serde_json::to_string_pretty(&serde_json::json!({"clean": true})).unwrap(); // safety: test
+        assert_eq!(action.output_raw.as_deref(), Some(expected_raw.as_str())); // safety: test
+        // output_sanitized wraps the string in a JSON string value
        assert_eq!(
+            /* safety: test */
            action.output_sanitized,
-            Some(serde_json::json!({"clean": true}))
+            Some(serde_json::json!("sanitized output"))
        );
-        assert_eq!(action.duration, Duration::from_secs(7));
+        assert_eq!(action.duration, Duration::from_secs(7)); // safety: test
    }

    #[test]
@@ -361,13 +370,13 @@ mod tests {
        let mut mem = ConversationMemory::new(10);
        mem.add(ChatMessage::user("hello"));
        mem.add(ChatMessage::assistant("hi"));
-        assert_eq!(mem.len(), 2);
-        assert!(!mem.is_empty());
+        assert_eq!(mem.len(), 2); // safety: test
+        assert!(!mem.is_empty()); // safety: test

        mem.clear();
-        assert_eq!(mem.len(), 0);
-        assert!(mem.is_empty());
-        assert!(mem.messages().is_empty());
+        assert_eq!(mem.len(), 0); // safety: test
+        assert!(mem.is_empty()); // safety: test
+        assert!(mem.messages().is_empty()); // safety: test
    }

    #[test]
@@ -379,20 +388,20 @@ mod tests {
        mem.add(ChatMessage::assistant("four"));

        let last_2 = mem.last_n(2);
-        assert_eq!(last_2.len(), 2);
-        assert_eq!(last_2[0].content, "three");
-        assert_eq!(last_2[1].content, "four");
+        assert_eq!(last_2.len(), 2); // safety: test
+        assert_eq!(last_2[0].content, "three"); // safety: test
+        assert_eq!(last_2[1].content, "four"); // safety: test

        // Requesting more than available returns all
        let last_100 = mem.last_n(100);
-        assert_eq!(last_100.len(), 4);
+        assert_eq!(last_100.len(), 4); // safety: test
    }

    #[test]
    fn test_conversation_memory_last_n_empty() {
        let mem = ConversationMemory::new(10);
        let result = mem.last_n(5);
-        assert!(result.is_empty());
+        assert!(result.is_empty()); // safety: test
    }

    #[test]
@@ -405,13 +414,13 @@ mod tests {
        // At capacity (3). Adding one more should trim, but keep system.
        mem.add(ChatMessage::user("msg3"));

-        assert_eq!(mem.len(), 3);
+        assert_eq!(mem.len(), 3); // safety: test
        // System message must survive
-        assert_eq!(mem.messages()[0].role, crate::llm::Role::System);
-        assert_eq!(mem.messages()[0].content, "You are helpful");
+        assert_eq!(mem.messages()[0].role, crate::llm::Role::System); // safety: test
+        assert_eq!(mem.messages()[0].content, "You are helpful"); // safety: test
        // Oldest non-system message (msg1) should be gone
-        assert_eq!(mem.messages()[1].content, "msg2");
-        assert_eq!(mem.messages()[2].content, "msg3");
+        assert_eq!(mem.messages()[1].content, "msg2"); // safety: test
+        assert_eq!(mem.messages()[2].content, "msg3"); // safety: test
    }

    #[test]
@@ -422,9 +431,9 @@ mod tests {
        // Now at capacity. Add another.
        mem.add(ChatMessage::user("b"));

-        assert_eq!(mem.len(), 2);
-        assert_eq!(mem.messages()[0].role, crate::llm::Role::System);
-        assert_eq!(mem.messages()[1].content, "b");
+        assert_eq!(mem.len(), 2); // safety: test
+        assert_eq!(mem.messages()[0].role, crate::llm::Role::System); // safety: test
+        assert_eq!(mem.messages()[1].content, "b"); // safety: test
    }

    #[test]
@@ -440,7 +449,7 @@ mod tests {
        mem.add(ChatMessage::user("hello"));
        // Should have broken out rather than looping forever.
        // The system message is protected, so len may exceed max.
-        assert!(mem.len() <= 2);
+        assert!(mem.len() <= 2); // safety: test
    }

    #[test]
@@ -459,14 +468,14 @@ mod tests {
            .fail("oops", Duration::from_millis(2));
        memory.record_action(err);

-        assert_eq!(memory.successful_actions(), 1);
-        assert_eq!(memory.failed_actions(), 1);
+        assert_eq!(memory.successful_actions(), 1); // safety: test
+        assert_eq!(memory.failed_actions(), 1); // safety: test
    }

    #[test]
    fn test_memory_last_action() {
        let mut memory = Memory::new(Uuid::new_v4());
-        assert!(memory.last_action().is_none());
+        assert!(memory.last_action().is_none()); // safety: test

        let a1 = memory
            .create_action("first", serde_json::json!({}))
@@ -478,8 +487,8 @@ mod tests {
            .fail("nope", Duration::ZERO);
        memory.record_action(a2);

-        let last = memory.last_action().unwrap();
-        assert_eq!(last.tool_name, "second");
+        let last = memory.last_action().unwrap(); // safety: test
+        assert_eq!(last.tool_name, "second"); // safety: test
    }

    #[test]
@@ -499,9 +508,9 @@ mod tests {
        );
        memory.record_action(a);

-        assert_eq!(memory.actions_by_tool("shell").len(), 3);
-        assert_eq!(memory.actions_by_tool("http").len(), 1);
-        assert_eq!(memory.actions_by_tool("nonexistent").len(), 0);
+        assert_eq!(memory.actions_by_tool("shell").len(), 3); // safety: test
+        assert_eq!(memory.actions_by_tool("http").len(), 1); // safety: test
+        assert_eq!(memory.actions_by_tool("nonexistent").len(), 0); // safety: test
    }

    #[test]
@@ -509,25 +518,25 @@ mod tests {
        let mut memory = Memory::new(Uuid::new_v4());

        let a0 = memory.create_action("t", serde_json::json!({}));
-        assert_eq!(a0.sequence, 0);
+        assert_eq!(a0.sequence, 0); // safety: test

        let a1 = memory.create_action("t", serde_json::json!({}));
-        assert_eq!(a1.sequence, 1);
+        assert_eq!(a1.sequence, 1); // safety: test

        let a2 = memory.create_action("t", serde_json::json!({}));
-        assert_eq!(a2.sequence, 2);
+        assert_eq!(a2.sequence, 2); // safety: test
    }

    #[test]
    fn test_memory_add_message_delegates_to_conversation() {
        let mut memory = Memory::new(Uuid::new_v4());
-        assert!(memory.conversation.is_empty());
+        assert!(memory.conversation.is_empty()); // safety: test

        memory.add_message(ChatMessage::user("hello"));
        memory.add_message(ChatMessage::assistant("hi"));

-        assert_eq!(memory.conversation.len(), 2);
-        assert_eq!(memory.conversation.messages()[0].content, "hello");
+        assert_eq!(memory.conversation.len(), 2); // safety: test
+        assert_eq!(memory.conversation.messages()[0].content, "hello"); // safety: test
    }

    #[test]
@@ -540,7 +549,7 @@ mod tests {
            .succeed(None, serde_json::json!({}), Duration::ZERO);
        memory.record_action(a);

-        assert_eq!(memory.total_cost(), Decimal::ZERO);
+        assert_eq!(memory.total_cost(), Decimal::ZERO); // safety: test
    }

    #[test]
@@ -560,6 +569,6 @@ mod tests {
        memory.record_action(a2);

        // Both successful and failed actions contribute to total duration
-        assert_eq!(memory.total_duration(), Duration::from_millis(300));
+        assert_eq!(memory.total_duration(), Duration::from_millis(300)); // safety: test
    }
 }
--- a/Show More
+++ b/Show More