fix(clippy): replace find().is_none() with !any() in user stats test

https://claude.ai/code/session_01Nm95eCjdrwxDjwkHTRieZs
fix(routines): address review feedback on retry loop
2026-08-25 14:53:34 +00:00 · 2026-03-28 19:22:38 +00:00 · 2026-03-28 19:16:10 +00:00 · 2026-03-28 19:16:10 +00:00 · 2026-03-28 19:16:10 +00:00 · 2026-03-28 19:16:10 +00:00
159 changed files with 16525 additions and 1711 deletions
@@ -12,6 +12,7 @@ jobs:
  tests:
    name: Tests (${{ matrix.name }})
    runs-on: ubuntu-latest
+    timeout-minutes: 45
    strategy:
      fail-fast: false
      matrix:
@@ -40,11 +41,14 @@ jobs:
      - name: Build WASM channels (for integration tests)
        run: ./scripts/build-wasm-extensions.sh --channels
      - name: Run Tests
-        run: cargo test ${{ matrix.flags }} -- --nocapture
+        run: |
+          timeout --signal=INT --kill-after=30s 40m \
+            cargo test ${{ matrix.flags }} -- --nocapture

  heavy-integration-tests:
    name: Heavy Integration Tests
    runs-on: ubuntu-latest
+    timeout-minutes: 20
    steps:
      - name: Checkout repository
        uses: actions/checkout@v6
@@ -58,9 +62,13 @@ jobs:
      - 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
+        run: |
+          timeout --signal=INT --kill-after=30s 15m \
+            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
+        run: |
+          timeout --signal=INT --kill-after=30s 10m \
+            cargo test --features integration --test telegram_auth_integration test_private_messages_use_chat_id_as_thread_scope -- --exact

  telegram-tests:
    name: Telegram Channel Tests
@@ -68,6 +76,7 @@ jobs:
      github.event_name != 'pull_request' ||
      github.base_ref != 'staging'
    runs-on: ubuntu-latest
+    timeout-minutes: 15
    steps:
      - name: Checkout repository
        uses: actions/checkout@v6
@@ -75,7 +84,9 @@ jobs:
        uses: dtolnay/rust-toolchain@stable
      - uses: Swatinem/rust-cache@v2
      - name: Run Telegram Channel Tests
-        run: cargo test --manifest-path channels-src/telegram/Cargo.toml -- --nocapture
+        run: |
+          timeout --signal=INT --kill-after=30s 10m \
+            cargo test --manifest-path channels-src/telegram/Cargo.toml -- --nocapture

  windows-build:
    name: Windows Build (${{ matrix.name }})
@@ -110,6 +121,7 @@ jobs:
      github.event_name != 'pull_request' ||
      github.base_ref != 'staging'
    runs-on: ubuntu-latest
+    timeout-minutes: 30
    steps:
      - name: Checkout repository
        uses: actions/checkout@v6
@@ -125,7 +137,9 @@ jobs:
      - name: Build all WASM extensions against current WIT
        run: ./scripts/build-wasm-extensions.sh
      - name: Instantiation test (host linker compatibility)
-        run: cargo test --all-features wit_compat -- --nocapture
+        run: |
+          timeout --signal=INT --kill-after=30s 20m \
+            cargo test --all-features wit_compat -- --nocapture

  bench-compile:
    name: Benchmark Compilation
@@ -7,6 +7,138 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0

 ## [Unreleased]

+## [0.22.0](https://github.com/nearai/ironclaw/compare/ironclaw-v0.21.0...ironclaw-v0.22.0) - 2026-03-25
+
+### Added
+
+- *(agent)* thread per-tool reasoning through provider, session, and all surfaces ([#1513](https://github.com/nearai/ironclaw/pull/1513))
+- *(cli)* show credential auth status in tool info ([#1572](https://github.com/nearai/ironclaw/pull/1572))
+- multi-tenant auth with per-user workspace isolation ([#1118](https://github.com/nearai/ironclaw/pull/1118))
+- *(cli)* add ironclaw models subcommands (list/status/set/set-provider) ([#1043](https://github.com/nearai/ironclaw/pull/1043))
+- *(workspace)* multi-scope workspace reads ([#1117](https://github.com/nearai/ironclaw/pull/1117))
+- *(ux)* complete UX overhaul — design system, onboarding, web polish ([#1277](https://github.com/nearai/ironclaw/pull/1277))
+- *(gemini_oauth)* full Gemini CLI OAuth integration with Cloud Code API ([#1356](https://github.com/nearai/ironclaw/pull/1356))
+- *(shell)* add Low/Medium/High risk levels for graduated command approval (closes #172) ([#368](https://github.com/nearai/ironclaw/pull/368))
+- *(agent)* queue and merge messages during active turns ([#1412](https://github.com/nearai/ironclaw/pull/1412))
+- *(cli)* add `ironclaw hooks list` subcommand ([#1023](https://github.com/nearai/ironclaw/pull/1023))
+- *(extensions)* support text setup fields in web configure modal ([#496](https://github.com/nearai/ironclaw/pull/496))
+- *(llm)* add GitHub Copilot as LLM provider ([#1512](https://github.com/nearai/ironclaw/pull/1512))
+- *(workspace)* layered memory with sensitivity-based privacy redirect ([#1112](https://github.com/nearai/ironclaw/pull/1112))
+- *(webhooks)* add public webhook trigger endpoint for routines ([#736](https://github.com/nearai/ironclaw/pull/736))
+- *(llm)* Add OpenAI Codex (ChatGPT subscription) as LLM provider ([#1461](https://github.com/nearai/ironclaw/pull/1461))
+- *(web)* add light theme with dark/light/system toggle ([#1457](https://github.com/nearai/ironclaw/pull/1457))
+- *(agent)* activate stuck_threshold for time-based stuck job detection ([#1234](https://github.com/nearai/ironclaw/pull/1234))
+- chat onboarding and routine advisor ([#927](https://github.com/nearai/ironclaw/pull/927))
+
+### Fixed
+
+- ensure LLM calls always end with user message (closes #763) ([#1259](https://github.com/nearai/ironclaw/pull/1259))
+- restore owner-scoped gateway startup ([#1625](https://github.com/nearai/ironclaw/pull/1625))
+- remove stale stream_token gate from channel-relay activation ([#1623](https://github.com/nearai/ironclaw/pull/1623))
+- *(agent)* case-insensitive channel match and user_id filter for event triggers ([#1211](https://github.com/nearai/ironclaw/pull/1211))
+- *(routines)* normalize status display across web and CLI ([#1469](https://github.com/nearai/ironclaw/pull/1469))
+- *(tunnel)* managed tunnels target wrong port and die from SIGPIPE ([#1093](https://github.com/nearai/ironclaw/pull/1093))
+- *(agent)* persist /model selection to .env, TOML, and DB ([#1581](https://github.com/nearai/ironclaw/pull/1581))
+- post-merge review sweep — 8 fixes across security, perf, and correctness ([#1550](https://github.com/nearai/ironclaw/pull/1550))
+- generate Mistral-compatible 9-char alphanumeric tool call IDs ([#1242](https://github.com/nearai/ironclaw/pull/1242))
+- *(mcp)* handle empty 202 notification acknowledgements ([#1539](https://github.com/nearai/ironclaw/pull/1539))
+- *(tests)* eliminate env mutex poison cascade ([#1558](https://github.com/nearai/ironclaw/pull/1558))
+- *(safety)* escape tool output XML content and remove misleading sanitized attr ([#1067](https://github.com/nearai/ironclaw/pull/1067))
+- *(oauth)* reject malformed ic2.* states in decode_hosted_oauth_state ([#1441](https://github.com/nearai/ironclaw/pull/1441)) ([#1454](https://github.com/nearai/ironclaw/pull/1454))
+- parameter coercion and validation for oneOf/anyOf/allOf schemas ([#1397](https://github.com/nearai/ironclaw/pull/1397))
+- persist startup-loaded MCP clients in ExtensionManager ([#1509](https://github.com/nearai/ironclaw/pull/1509))
+- *(deps)* patch rustls-webpki vulnerability (RUSTSEC-2026-0049)
+- *(routines)* add missing extension_manager field in trigger_manual EngineContext
+- *(ci)* serialize env-mutating OAuth wildcard tests with ENV_MUTEX ([#1280](https://github.com/nearai/ironclaw/pull/1280)) ([#1468](https://github.com/nearai/ironclaw/pull/1468))
+- *(setup)* remove redundant LLM config and API keys from bootstrap .env ([#1448](https://github.com/nearai/ironclaw/pull/1448))
+- resolve wasm broadcast merge conflicts with staging ([#395](https://github.com/nearai/ironclaw/pull/395)) ([#1460](https://github.com/nearai/ironclaw/pull/1460))
+- skip credential validation for Bedrock backend ([#1011](https://github.com/nearai/ironclaw/pull/1011))
+- register sandbox jobs in ContextManager for query tool visibility ([#1426](https://github.com/nearai/ironclaw/pull/1426))
+- prefer execution-local message routing metadata ([#1449](https://github.com/nearai/ironclaw/pull/1449))
+- *(security)* validate embedding base URLs to prevent SSRF ([#1221](https://github.com/nearai/ironclaw/pull/1221))
+- f32→f64 precision artifact in temperature causes provider 400 errors ([#1450](https://github.com/nearai/ironclaw/pull/1450))
+- *(routines)* surface errors when sandbox unavailable for full_job routines ([#769](https://github.com/nearai/ironclaw/pull/769))
+- restore libSQL vector search with dynamic dimensions ([#1393](https://github.com/nearai/ironclaw/pull/1393))
+- staging CI triage — consolidate retry parsing, fix flaky tests, add docs ([#1427](https://github.com/nearai/ironclaw/pull/1427))
+
+### Other
+
+- Merge branch 'main' into staging-promote/455f543b-23329172268
+- Merge pull request #1655 from nearai/codex/fix-staging-promotion-1451-version-bumps
+- Merge pull request #1499 from nearai/staging-promote/9603fefd-23364438978
+- Fix libsql prompt scope regressions ([#1651](https://github.com/nearai/ironclaw/pull/1651))
+- Normalize cron schedules on routine create ([#1648](https://github.com/nearai/ironclaw/pull/1648))
+- Fix MCP lifecycle trace user scope ([#1646](https://github.com/nearai/ironclaw/pull/1646))
+- Fix REPL single-message hang and cap CI test duration ([#1643](https://github.com/nearai/ironclaw/pull/1643))
+- extract AppEvent to crates/ironclaw_common ([#1615](https://github.com/nearai/ironclaw/pull/1615))
+- Fix hosted OAuth refresh via proxy ([#1602](https://github.com/nearai/ironclaw/pull/1602))
+- *(agent)* optimize approval thread resolution (UUID parsing + lock contention) ([#1592](https://github.com/nearai/ironclaw/pull/1592))
+- *(tools)* auto-compact WASM tool schemas, add descriptions, improve credential prompts ([#1525](https://github.com/nearai/ironclaw/pull/1525))
+- Default new lightweight routines to tools-enabled ([#1573](https://github.com/nearai/ironclaw/pull/1573))
+- Google OAuth URL broken when initiated from Telegram channel ([#1165](https://github.com/nearai/ironclaw/pull/1165))
+- add gitcgr code graph badge ([#1563](https://github.com/nearai/ironclaw/pull/1563))
+- Fix owner-scoped message routing fallbacks ([#1574](https://github.com/nearai/ironclaw/pull/1574))
+- *(tools)* remove unconditional params clone in shared execution (fix #893) ([#926](https://github.com/nearai/ironclaw/pull/926))
+- *(llm)* move transcription module into src/llm/ ([#1559](https://github.com/nearai/ironclaw/pull/1559))
+- *(agent)* avoid preview allocations for non-truncated strings (fix #894) ([#924](https://github.com/nearai/ironclaw/pull/924))
+- Expand AGENTS.md with coding agents guidance ([#1392](https://github.com/nearai/ironclaw/pull/1392))
+- Fix CI approval flows and stale fixtures ([#1478](https://github.com/nearai/ironclaw/pull/1478))
+- Use live owner tool scope for autonomous routines and jobs ([#1453](https://github.com/nearai/ironclaw/pull/1453))
+- use Arc in embedding cache to avoid clones on miss path ([#1438](https://github.com/nearai/ironclaw/pull/1438))
+- Add owner-scoped permissions for full-job routines ([#1440](https://github.com/nearai/ironclaw/pull/1440))
+
+## [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
@@ -2323,7 +2323,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "39cab71617ae0d63f51a36d69f866391735b51691dbda63cf6f96d042b63efeb"
 dependencies = [
 "libc",
- "windows-sys 0.52.0",
+ "windows-sys 0.59.0",
 ]

 [[package]]
@@ -3150,7 +3150,7 @@ dependencies = [
 "libc",
 "percent-encoding",
 "pin-project-lite",
- "socket2 0.5.10",
+ "socket2 0.6.3",
 "system-configuration",
 "tokio",
 "tower-service",
@@ -3390,7 +3390,7 @@ dependencies = [

 [[package]]
 name = "ironclaw"
-version = "0.19.0"
+version = "0.22.0"
 dependencies = [
 "aes-gcm",
 "aho-corasick",
@@ -3428,6 +3428,7 @@ dependencies = [
 "hyper-util",
 "iana-time-zone",
 "insta",
+ "ironclaw_common",
 "ironclaw_safety",
 "json5",
 "libsql",
@@ -3438,6 +3439,7 @@ dependencies = [
 "pgvector",
 "postgres-types",
 "pretty_assertions",
+ "pty-process",
 "rand 0.8.5",
 "readabilityrs",
 "refinery",
@@ -3481,13 +3483,22 @@ dependencies = [
 "wasmparser 0.220.1",
 "wasmtime",
 "wasmtime-wasi",
+ "webpki-roots 0.26.11",
 "zbus",
 "zip",
 ]

 [[package]]
-name = "ironclaw_safety"
+name = "ironclaw_common"
 version = "0.1.0"
+dependencies = [
+ "serde",
+ "serde_json",
+]
+
+[[package]]
+name = "ironclaw_safety"
+version = "0.2.0"
 dependencies = [
 "aho-corasick",
 "regex",
@@ -3514,7 +3525,7 @@ checksum = "3640c1c38b8e4e43584d8df18be5fc6b0aa314ce6ebf51b53313d4306cca8e46"
 dependencies = [
 "hermit-abi",
 "libc",
- "windows-sys 0.59.0",
+ "windows-sys 0.61.2",
 ]

 [[package]]
@@ -4896,6 +4907,16 @@ dependencies = [
 "syn 1.0.109",
 ]

+[[package]]
+name = "pty-process"
+version = "0.5.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "71cec9e2670207c5ebb9e477763c74436af3b9091dd550b9fb3c1bec7f3ea266"
+dependencies = [
+ "rustix 1.1.4",
+ "tokio",
+]
+
 [[package]]
 name = "pulley-interpreter"
 version = "28.0.1"
@@ -4920,7 +4941,7 @@ dependencies = [
 "quinn-udp",
 "rustc-hash 2.1.1",
 "rustls 0.23.37",
- "socket2 0.5.10",
+ "socket2 0.6.3",
 "thiserror 2.0.18",
 "tokio",
 "tracing",
@@ -4957,9 +4978,9 @@ dependencies = [
 "cfg_aliases",
 "libc",
 "once_cell",
- "socket2 0.5.10",
+ "socket2 0.6.3",
 "tracing",
- "windows-sys 0.59.0",
+ "windows-sys 0.60.2",
 ]

 [[package]]
@@ -5472,7 +5493,7 @@ dependencies = [
 "errno",
 "libc",
 "linux-raw-sys 0.12.1",
- "windows-sys 0.52.0",
+ "windows-sys 0.59.0",
 ]

 [[package]]
@@ -6379,7 +6400,7 @@ dependencies = [
 "getrandom 0.4.2",
 "once_cell",
 "rustix 1.1.4",
- "windows-sys 0.52.0",
+ "windows-sys 0.59.0",
 ]

 [[package]]
@@ -6982,6 +7003,7 @@ dependencies = [
 "futures-util",
 "http 1.4.0",
 "http-body 1.0.1",
+ "http-body-util",
 "iri-string",
 "pin-project-lite",
 "tower 0.5.3",
@@ -1,5 +1,5 @@
 [workspace]
-members = [".", "crates/ironclaw_safety"]
+members = [".", "crates/ironclaw_common", "crates/ironclaw_safety"]
 exclude = [
    "channels-src/discord",
    "channels-src/telegram",
@@ -20,7 +20,7 @@ exclude = [

 [package]
 name = "ironclaw"
-version = "0.19.0"
+version = "0.22.0"
 edition = "2024"
 rust-version = "1.92"
 description = "Secure personal AI assistant that protects your data and expands its capabilities on the fly"
@@ -57,6 +57,7 @@ refinery = { version = "0.8", features = ["tokio-postgres"], optional = true }
 tokio-postgres-rustls = { version = "0.13", optional = true }
 rustls = { version = "0.23", optional = true, default-features = false }
 rustls-native-certs = { version = "0.8", optional = true }
+webpki-roots = { version = "0.26", optional = true }

 # Database - libSQL/Turso (optional embedded database)
 libsql = { version = "0.6", optional = true, default-features = false, features = ["core", "replication", "remote", "tls"] }
@@ -95,13 +96,16 @@ termimad = "0.34"
 # Channel integrations
 axum = { version = "0.8", features = ["ws"] }
 tower = "0.5"
-tower-http = { version = "0.6", features = ["trace", "cors", "set-header"] }
+tower-http = { version = "0.6", features = ["trace", "cors", "set-header", "catch-panic"] }

 # Cron scheduling for routines
 cron = "0.13"

+# Shared types
+ironclaw_common = { path = "crates/ironclaw_common", version = "0.1.0" }
+
 # Safety/sanitization
-ironclaw_safety = { path = "crates/ironclaw_safety", version = "0.1.0" }
+ironclaw_safety = { path = "crates/ironclaw_safety", version = "0.2.0" }
 regex = "1"
 aho-corasick = "1"

@@ -185,6 +189,10 @@ json5 = { version = "0.4", optional = true }
 [target.'cfg(target_os = "macos")'.dependencies]
 security-framework = "3"

+# PTY allocation for Claude CLI stdout buffering fix (Unix only)
+[target.'cfg(unix)'.dependencies]
+pty-process = { version = "0.5", features = ["async"] }
+
 # Linux secret-service (GNOME Keyring, KWallet)
 [target.'cfg(target_os = "linux")'.dependencies]
 secret-service = { version = "4", features = ["rt-tokio-crypto-rust"] }
@@ -216,6 +224,7 @@ postgres = [
    "dep:tokio-postgres-rustls",
    "dep:rustls",
    "dep:rustls-native-certs",
+    "dep:webpki-roots",
    "dep:postgres-types",
    "dep:refinery",
    "dep:pgvector",
@@ -1,45 +1,71 @@
 # Multi-stage Dockerfile for the IronClaw agent (cloud deployment).
 #
+# Uses cargo-chef for dependency caching — only rebuilds deps when
+# Cargo.toml/Cargo.lock change, not on every source edit.
+#
 # Build:
 #   docker build --platform linux/amd64 -t ironclaw:latest .
 #
 # Run:
 #   docker run --env-file .env -p 3000:3000 ironclaw:latest

-# Stage 1: Build
-FROM rust:1.92-slim-bookworm AS builder
+# Stage 1: Install cargo-chef
+FROM rust:1.92-slim-bookworm AS chef

 RUN apt-get update && apt-get install -y --no-install-recommends \
    pkg-config libssl-dev cmake gcc g++ \
    && rm -rf /var/lib/apt/lists/* \
    && rustup target add wasm32-wasip2 \
-    && cargo install wasm-tools
+    && cargo install cargo-chef wasm-tools

 WORKDIR /app

-# Copy manifests first for layer caching
+# Stage 2: Generate the dependency recipe (changes only when Cargo.toml/lock change)
+FROM chef AS planner
+
 COPY Cargo.toml Cargo.lock ./
 COPY crates/ crates/
-
-# Copy source, build script, tests, and supporting directories
 COPY build.rs build.rs
 COPY src/ src/
 COPY tests/ tests/
+COPY benches/ benches/
 COPY migrations/ migrations/
 COPY registry/ registry/
 COPY channels-src/ channels-src/
 COPY wit/ wit/
 COPY providers.json providers.json
-# [[bench]] entries in Cargo.toml require bench sources to exist for cargo to parse the manifest
+
+RUN cargo chef prepare --recipe-path recipe.json
+
+# Stage 3: Build dependencies (cached unless Cargo.toml/lock change)
+FROM chef AS deps
+
+COPY --from=planner /app/recipe.json recipe.json
+RUN cargo chef cook --release --recipe-path recipe.json
+
+# Stage 4: Build the actual binary (only recompiles ironclaw source)
+FROM deps AS builder
+
+COPY Cargo.toml Cargo.lock ./
+COPY crates/ crates/
+COPY build.rs build.rs
+COPY src/ src/
+COPY tests/ tests/
 COPY benches/ benches/
+COPY migrations/ migrations/
+COPY registry/ registry/
+COPY channels-src/ channels-src/
+COPY wit/ wit/
+COPY providers.json providers.json

 RUN cargo build --release --bin ironclaw

-# Stage 2: Runtime
+# Stage 5: Runtime
 FROM debian:bookworm-slim

 RUN apt-get update && apt-get install -y --no-install-recommends \
    ca-certificates libssl3 \
+    && update-ca-certificates \
    && rm -rf /var/lib/apt/lists/*

 COPY --from=builder /app/target/release/ironclaw /usr/local/bin/ironclaw
@@ -28,6 +28,9 @@ use std::{cmp::Ordering, collections::HashMap};
 use ed25519_dalek::{Signature, Verifier, VerifyingKey};
 use serde::{Deserialize, Serialize};

+/// Discord REST API v10 base URL.
+const DISCORD_API_BASE: &str = "https://discord.com/api/v10";
+
 use exports::near::agent::channel::{
    AgentResponse, ChannelConfig, Guest, HttpEndpointConfig, IncomingHttpRequest,
    OutgoingHttpResponse, PollConfig, StatusUpdate,
@@ -427,7 +430,7 @@ impl Guest for DiscordChannel {
            (
                "PATCH",
                format!(
-                    "https://discord.com/api/v10/webhooks/{}/{}/messages/@original",
+                    "{DISCORD_API_BASE}/webhooks/{}/{}/messages/@original",
                    application_id, token
                ),
            )
@@ -438,20 +441,7 @@ impl Guest for DiscordChannel {
            payload["allowed_mentions"] = serde_json::json!({
                "replied_user": true
            });
-            let mention_payload = serde_json::to_vec(&payload)
-                .map_err(|e| format!("Failed to serialize mention payload: {}", e))?;
-            let mention_url = format!(
-                "https://discord.com/api/v10/channels/{}/messages",
-                metadata.channel_id
-            );
-            let result = channel_host::http_request(
-                "POST",
-                &mention_url,
-                &discord_auth_headers_json(true),
-                Some(&mention_payload),
-                None,
-            );
-            return map_discord_response(result);
+            return send_channel_message(&metadata.channel_id, payload);
        } else {
            return Err("Unsupported Discord response metadata".to_string());
        };
@@ -469,8 +459,8 @@ impl Guest for DiscordChannel {

    fn on_status(_update: StatusUpdate) {}

-    fn on_broadcast(_user_id: String, _response: AgentResponse) -> Result<(), String> {
-        Err("broadcast not yet implemented for Discord channel".to_string())
+    fn on_broadcast(user_id: String, response: AgentResponse) -> Result<(), String> {
+        broadcast_dm(&user_id, &response.content)
    }

    fn on_shutdown() {
@@ -501,6 +491,21 @@ fn map_discord_response(
    }
 }

+/// Post a JSON payload to a Discord channel as a new message.
+fn send_channel_message(channel_id: &str, payload: serde_json::Value) -> Result<(), String> {
+    let payload_bytes = serde_json::to_vec(&payload)
+        .map_err(|e| format!("Failed to serialize message: {}", e))?;
+    let url = format!("{DISCORD_API_BASE}/channels/{}/messages", channel_id);
+    let result = channel_host::http_request(
+        "POST",
+        &url,
+        &discord_auth_headers_json(true),
+        Some(&payload_bytes),
+        None,
+    );
+    map_discord_response(result)
+}
+
 fn load_runtime_config() -> DiscordRuntimeConfig {
    channel_host::workspace_read("config.json")
        .and_then(|raw| serde_json::from_str::<DiscordRuntimeConfig>(&raw).ok())
@@ -539,7 +544,7 @@ fn get_or_fetch_bot_id() -> Option<String> {

    let response = channel_host::http_request(
        "GET",
-        "https://discord.com/api/v10/users/@me",
+        &format!("{DISCORD_API_BASE}/users/@me"),
        &discord_auth_headers_json(false),
        None,
        Some(10_000),
@@ -659,7 +664,7 @@ fn poll_channel_mentions(channel_id: &str, bot_id: &str) {

 fn fetch_latest_message_id(channel_id: &str) -> Option<String> {
    let url = format!(
-        "https://discord.com/api/v10/channels/{}/messages?limit=1",
+        "{DISCORD_API_BASE}/channels/{}/messages?limit=1",
        channel_id
    );
    let response = channel_host::http_request(
@@ -697,7 +702,7 @@ fn fetch_messages_after_cursor(

    for page in 0..MAX_PAGES {
        let url = format!(
-            "https://discord.com/api/v10/channels/{}/messages?limit={}&after={}",
+            "{DISCORD_API_BASE}/channels/{}/messages?limit={}&after={}",
            channel_id, PAGE_LIMIT, after
        );
        let response = match channel_host::http_request(
@@ -986,7 +991,7 @@ fn handle_slash_command(interaction: &DiscordInteraction) -> bool {
            );
            // Attempt to notify user of internal error
            let url = format!(
-                "https://discord.com/api/v10/webhooks/{}/{}",
+                "{DISCORD_API_BASE}/webhooks/{}/{}",
                interaction.application_id, interaction.token
            );
            let payload = serde_json::json!({
@@ -1106,7 +1111,7 @@ fn check_sender_permission(
    }

    let dm_policy =
-        channel_host::workspace_read(DM_POLICY_PATH).unwrap_or_else(|| default_dm_policy());
+        channel_host::workspace_read(DM_POLICY_PATH).unwrap_or_else(default_dm_policy);
    if dm_policy == "open" {
        return true;
    }
@@ -1161,7 +1166,7 @@ fn check_sender_permission(
 /// Send a pairing code as an ephemeral Discord followup message.
 fn send_pairing_reply(ctx: &PairingReplyCtx, code: &str) -> Result<(), String> {
    let url = format!(
-        "https://discord.com/api/v10/webhooks/{}/{}",
+        "{DISCORD_API_BASE}/webhooks/{}/{}",
        ctx.application_id, ctx.token
    );
    let payload = serde_json::json!({
@@ -1194,6 +1199,57 @@ fn send_pairing_reply(ctx: &PairingReplyCtx, code: &str) -> Result<(), String> {
    }
 }

+/// Send a broadcast message to a Discord user via DM.
+///
+/// Creates a DM channel with the user (Discord caches this, so repeated calls
+/// for the same user reuse the existing channel) and then posts the message.
+fn broadcast_dm(user_id: &str, content: &str) -> Result<(), String> {
+    // Validate user_id is a plausible Discord snowflake (numeric, 17-20 digits)
+    // to avoid injecting arbitrary strings into API URLs.
+    if user_id.is_empty()
+        || !user_id.chars().all(|c| c.is_ascii_digit())
+        || user_id.len() < 17
+        || user_id.len() > 20
+    {
+        return Err(format!("Invalid Discord user ID: '{}'", user_id));
+    }
+
+    // Step 1: Open (or reuse) a DM channel with the target user.
+    let create_dm_payload = serde_json::json!({ "recipient_id": user_id });
+    let create_dm_bytes = serde_json::to_vec(&create_dm_payload)
+        .map_err(|e| format!("Failed to serialize DM channel request: {}", e))?;
+
+    let dm_response = channel_host::http_request(
+        "POST",
+        &format!("{DISCORD_API_BASE}/users/@me/channels"),
+        &discord_auth_headers_json(true),
+        Some(&create_dm_bytes),
+        Some(10_000),
+    )
+    .map_err(|e| format!("Failed to create DM channel: {}", e))?;
+
+    if !(200..300).contains(&dm_response.status) {
+        let body = String::from_utf8_lossy(&dm_response.body);
+        return Err(format!(
+            "Discord create-DM failed: {} - {}",
+            dm_response.status, body
+        ));
+    }
+
+    #[derive(Deserialize)]
+    struct DmChannelResponse {
+        id: String,
+    }
+    let dm_channel: DmChannelResponse = serde_json::from_slice(&dm_response.body)
+        .map_err(|e| format!("Failed to parse DM channel response: {}", e))?;
+    let channel_id = &dm_channel.id;
+
+    // Step 2: Send the message to the DM channel.
+    let truncated = truncate_message(content);
+    let payload = serde_json::json!({ "content": truncated });
+    send_channel_message(channel_id, payload)
+}
+
 fn json_response(status: u16, value: serde_json::Value) -> OutgoingHttpResponse {
    let body = serde_json::to_vec(&value).unwrap_or_default();
    let headers = serde_json::json!({"Content-Type": "application/json"});
@@ -1593,4 +1649,43 @@ mod tests {
        assert_eq!(interaction.interaction_type, 2);
        assert!(interaction.data.is_some());
    }
+
+    #[test]
+    fn test_broadcast_dm_payload_format() {
+        // Verify the DM channel creation payload is well-formed JSON that
+        // Discord's API expects.
+        let user_id = "123456789012345678";
+        let payload = serde_json::json!({ "recipient_id": user_id });
+        let serialized = serde_json::to_vec(&payload).unwrap();
+        let parsed: serde_json::Value = serde_json::from_slice(&serialized).unwrap();
+        assert_eq!(
+            parsed.get("recipient_id").and_then(|v| v.as_str()),
+            Some(user_id)
+        );
+    }
+
+    #[test]
+    fn test_broadcast_message_truncation() {
+        // Broadcast uses truncate_message, verify it handles content within
+        // Discord's 2000-char limit for DMs.
+        let short = "Hello from broadcast";
+        assert_eq!(truncate_message(short), short);
+
+        let long = "x".repeat(2500);
+        let result = truncate_message(&long);
+        assert!(result.len() <= 2006); // 1990 content + 16 suffix
+        assert!(result.ends_with("\n... (truncated)"));
+    }
+
+    #[test]
+    fn test_broadcast_dm_validates_snowflake() {
+        // broadcast_dm rejects invalid Discord snowflake IDs before making
+        // any API calls. We can call it directly since invalid IDs are
+        // rejected before any host function is invoked.
+        assert!(broadcast_dm("", "hi").is_err());
+        assert!(broadcast_dm("abc", "hi").is_err());
+        assert!(broadcast_dm("12345", "hi").is_err()); // too short
+        assert!(broadcast_dm("123456789012345678901", "hi").is_err()); // too long
+        assert!(broadcast_dm("12345678901234567x", "hi").is_err()); // non-digit
+    }
 }
@@ -44,6 +44,7 @@ version = "0.1.0"
 dependencies = [
 "serde",
 "serde_json",
+ "subtle",
 "wit-bindgen",
 ]

@@ -208,6 +209,12 @@ dependencies = [
 "smallvec",
 ]

+[[package]]
+name = "subtle"
+version = "2.6.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "13c2bddecc57b384dee18652358fb23172facb8a2c51ccc10d74c157bdea3292"
+
 [[package]]
 name = "syn"
 version = "2.0.117"
@@ -15,6 +15,7 @@ wit-bindgen = "0.36"
 # Serialization
 serde = { version = "1.0", features = ["derive"] }
 serde_json = "1.0"
+subtle = "2.6"

 # Exclude from parent workspace (this is a standalone WASM component)

@@ -27,7 +27,7 @@
      {
        "name": "feishu_verification_token",
        "prompt": "Enter your Feishu/Lark Verification Token (from Event Subscription webhook settings)",
-        "optional": true
+        "optional": false
      }
    ],
    "setup_url": "https://open.feishu.cn/app"
@@ -63,13 +63,15 @@
      },
      "webhook": {
        "secret_header": "X-Feishu-Verification-Token",
-        "secret_name": "feishu_verification_token"
+        "secret_name": "feishu_verification_token",
+        "managed_by_host": false
      }
    }
  },
  "config": {
    "app_id": null,
    "app_secret": null,
+    "verification_token": null,
    "api_base": "https://open.feishu.cn",
    "owner_id": null,
    "dm_policy": "pairing",
@@ -23,7 +23,8 @@
 //! - App credentials (app_id, app_secret) are injected by the host into
 //!   the config JSON during startup for token exchange
 //! - Bearer token for API calls is obtained via token exchange and cached
-//! - Verification token validated by host for webhook requests
+//! - Webhook requests must be authenticated by the host or by a matching
+//!   Feishu verification token in the request body

 // Generate bindings from the WIT file
 wit_bindgen::generate!({
@@ -32,6 +33,7 @@ wit_bindgen::generate!({
 });

 use serde::{Deserialize, Serialize};
+use subtle::ConstantTimeEq;

 // Re-export generated types
 use exports::near::agent::channel::{
@@ -50,6 +52,7 @@ const ALLOW_FROM_PATH: &str = "allow_from";
 const API_BASE_PATH: &str = "api_base";
 const APP_ID_PATH: &str = "app_id";
 const APP_SECRET_PATH: &str = "app_secret";
+const VERIFICATION_TOKEN_PATH: &str = "verification_token";
 const TOKEN_PATH: &str = "tenant_access_token";
 const TOKEN_EXPIRY_PATH: &str = "token_expiry";

@@ -102,6 +105,10 @@ struct FeishuEventHeader {
    /// Tenant key.
    #[serde(default)]
    tenant_key: Option<String>,
+
+    /// Verification token for v2 event payloads.
+    #[serde(default)]
+    token: Option<String>,
 }

 /// Message receive event payload (im.message.receive_v1).
@@ -251,6 +258,9 @@ struct FeishuConfig {
    /// Feishu App Secret (for token exchange).
    app_secret: Option<String>,

+    /// Feishu Event Subscription verification token.
+    verification_token: Option<String>,
+
    /// API base URL. Defaults to "https://open.feishu.cn" (use
    /// "https://open.larksuite.com" for Lark international).
    #[serde(default = "default_api_base")]
@@ -300,6 +310,9 @@ impl Guest for FeishuChannel {
        if let Some(ref app_secret) = config.app_secret {
            let _ = channel_host::workspace_write(APP_SECRET_PATH, app_secret);
        }
+        if let Some(ref verification_token) = config.verification_token {
+            let _ = channel_host::workspace_write(VERIFICATION_TOKEN_PATH, verification_token);
+        }

        if let Some(owner_id) = &config.owner_id {
            let _ = channel_host::workspace_write(OWNER_ID_PATH, owner_id);
@@ -376,6 +389,23 @@ impl Guest for FeishuChannel {
            }
        };

+        let configured_token =
+            channel_host::workspace_read(VERIFICATION_TOKEN_PATH).filter(|token| !token.is_empty());
+        if !is_authenticated_webhook(
+            req.secret_validated,
+            configured_token.as_deref(),
+            request_verification_token(&event),
+        ) {
+            channel_host::log(
+                channel_host::LogLevel::Warn,
+                "Rejecting unauthenticated Feishu webhook request",
+            );
+            return json_response(
+                401,
+                serde_json::json!({"error": "Webhook authentication failed"}),
+            );
+        }
+
        // Handle URL verification challenge (initial webhook setup).
        if event.event_type.as_deref() == Some("url_verification") {
            if let Some(challenge) = &event.challenge {
@@ -839,6 +869,31 @@ fn json_response(status: u16, body: serde_json::Value) -> OutgoingHttpResponse {
    }
 }

+fn is_authenticated_webhook(
+    secret_validated: bool,
+    configured_token: Option<&str>,
+    request_token: Option<&str>,
+) -> bool {
+    if secret_validated {
+        return true;
+    }
+
+    match (configured_token, request_token) {
+        (Some(expected), Some(provided)) => {
+            bool::from(expected.as_bytes().ct_eq(provided.as_bytes()))
+        }
+        _ => false,
+    }
+}
+
+fn request_verification_token(event: &FeishuEvent) -> Option<&str> {
+    event
+        .header
+        .as_ref()
+        .and_then(|header| header.token.as_deref())
+        .or(event.token.as_deref())
+}
+
 #[cfg(test)]
 mod tests {
    use super::*;
@@ -862,7 +917,10 @@ mod tests {
    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");
+        assert!(
+            result.is_err(),
+            "should fail when tenant_access_token is missing"
+        );
    }

    #[test]
@@ -894,4 +952,64 @@ mod tests {
        assert_eq!(resp.code, 10003);
        assert!(resp.tenant_access_token.is_empty());
    }
+
+    #[test]
+    fn webhook_auth_requires_host_auth_or_matching_verification_token() {
+        assert!(
+            !is_authenticated_webhook(false, None, Some("token")),
+            "requests without any configured verification mechanism must be rejected"
+        );
+        assert!(
+            !is_authenticated_webhook(false, Some("expected"), None),
+            "requests missing the Feishu token must be rejected when host auth did not pass"
+        );
+        assert!(
+            !is_authenticated_webhook(false, Some("expected"), Some("wrong")),
+            "requests with the wrong Feishu token must be rejected"
+        );
+        assert!(
+            is_authenticated_webhook(false, Some("expected"), Some("expected")),
+            "matching Feishu verification token should authenticate the request"
+        );
+        assert!(
+            is_authenticated_webhook(true, None, None),
+            "host-authenticated requests should still be accepted"
+        );
+        assert!(
+            is_authenticated_webhook(true, Some("expected"), Some("wrong")),
+            "host authentication should take precedence over body token checks"
+        );
+    }
+
+    #[test]
+    fn request_verification_token_prefers_v2_header_token() {
+        let event: FeishuEvent = serde_json::from_str(
+            r#"{
+                "schema": "2.0",
+                "header": {
+                    "event_id": "evt_123",
+                    "event_type": "im.message.receive_v1",
+                    "token": "header-token"
+                },
+                "event": {}
+            }"#,
+        )
+        .unwrap();
+
+        assert_eq!(request_verification_token(&event), Some("header-token"));
+    }
+
+    #[test]
+    fn request_verification_token_falls_back_to_top_level_token() {
+        let event: FeishuEvent = serde_json::from_str(
+            r#"{
+                "type": "url_verification",
+                "challenge": "abc",
+                "token": "top-level-token"
+            }"#,
+        )
+        .unwrap();
+
+        assert_eq!(request_verification_token(&event), Some("top-level-token"));
+    }
 }
@@ -0,0 +1,17 @@
+[package]
+name = "ironclaw_common"
+version = "0.1.0"
+edition = "2024"
+rust-version = "1.92"
+description = "Shared types and utilities for the IronClaw workspace"
+authors = ["NEAR AI <[email protected]>"]
+license = "MIT OR Apache-2.0"
+homepage = "https://github.com/nearai/ironclaw"
+repository = "https://github.com/nearai/ironclaw"
+
+[package.metadata.dist]
+dist = false
+
+[dependencies]
+serde = { version = "1", features = ["derive"] }
+serde_json = "1"
@@ -0,0 +1,393 @@
+//! Application-wide event types.
+//!
+//! `AppEvent` is the real-time event protocol used across the entire
+//! application.  The web gateway serialises these to SSE / WebSocket
+//! frames, but other subsystems (agent loop, orchestrator, extensions)
+//! produce and consume them too.
+
+use serde::{Deserialize, Serialize};
+
+/// A single tool decision in a reasoning update (SSE DTO).
+#[derive(Debug, Clone, Serialize, Deserialize)]
+pub struct ToolDecisionDto {
+    pub tool_name: String,
+    pub rationale: String,
+}
+
+impl ToolDecisionDto {
+    /// Parse a list of tool decisions from a JSON array value.
+    pub fn from_json_array(value: &serde_json::Value) -> Vec<Self> {
+        value
+            .as_array()
+            .map(|arr| {
+                arr.iter()
+                    .filter_map(|d| {
+                        Some(Self {
+                            tool_name: d.get("tool_name")?.as_str()?.to_string(),
+                            rationale: d.get("rationale")?.as_str()?.to_string(),
+                        })
+                    })
+                    .collect()
+            })
+            .unwrap_or_default()
+    }
+}
+
+#[derive(Debug, Clone, Serialize, Deserialize)]
+#[serde(tag = "type")]
+pub enum AppEvent {
+    #[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>,
+    },
+
+    /// Per-turn token usage and cost summary.
+    #[serde(rename = "turn_cost")]
+    TurnCost {
+        input_tokens: u64,
+        output_tokens: u64,
+        cost_usd: 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>,
+    },
+
+    /// Agent reasoning update (why it chose specific tools).
+    #[serde(rename = "reasoning_update")]
+    ReasoningUpdate {
+        narrative: String,
+        decisions: Vec<ToolDecisionDto>,
+        #[serde(skip_serializing_if = "Option::is_none")]
+        thread_id: Option<String>,
+    },
+
+    /// Reasoning update for a sandbox job.
+    #[serde(rename = "job_reasoning")]
+    JobReasoning {
+        job_id: String,
+        narrative: String,
+        decisions: Vec<ToolDecisionDto>,
+    },
+}
+
+impl AppEvent {
+    /// The wire-format event type string (matches the `#[serde(rename)]` value).
+    pub fn event_type(&self) -> &'static str {
+        match self {
+            Self::Response { .. } => "response",
+            Self::Thinking { .. } => "thinking",
+            Self::ToolStarted { .. } => "tool_started",
+            Self::ToolCompleted { .. } => "tool_completed",
+            Self::ToolResult { .. } => "tool_result",
+            Self::StreamChunk { .. } => "stream_chunk",
+            Self::Status { .. } => "status",
+            Self::JobStarted { .. } => "job_started",
+            Self::ApprovalNeeded { .. } => "approval_needed",
+            Self::AuthRequired { .. } => "auth_required",
+            Self::AuthCompleted { .. } => "auth_completed",
+            Self::Error { .. } => "error",
+            Self::Heartbeat => "heartbeat",
+            Self::JobMessage { .. } => "job_message",
+            Self::JobToolUse { .. } => "job_tool_use",
+            Self::JobToolResult { .. } => "job_tool_result",
+            Self::JobStatus { .. } => "job_status",
+            Self::JobResult { .. } => "job_result",
+            Self::ImageGenerated { .. } => "image_generated",
+            Self::Suggestions { .. } => "suggestions",
+            Self::TurnCost { .. } => "turn_cost",
+            Self::ExtensionStatus { .. } => "extension_status",
+            Self::ReasoningUpdate { .. } => "reasoning_update",
+            Self::JobReasoning { .. } => "job_reasoning",
+        }
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    /// Verify that `event_type()` returns the same string as the serde
+    /// `"type"` field for every variant.  This catches drift between the
+    /// `#[serde(rename)]` attributes and the manual match arms.
+    #[test]
+    fn event_type_matches_serde_type_field() {
+        let variants: Vec<AppEvent> = vec![
+            AppEvent::Response {
+                content: String::new(),
+                thread_id: String::new(),
+            },
+            AppEvent::Thinking {
+                message: String::new(),
+                thread_id: None,
+            },
+            AppEvent::ToolStarted {
+                name: String::new(),
+                thread_id: None,
+            },
+            AppEvent::ToolCompleted {
+                name: String::new(),
+                success: true,
+                error: None,
+                parameters: None,
+                thread_id: None,
+            },
+            AppEvent::ToolResult {
+                name: String::new(),
+                preview: String::new(),
+                thread_id: None,
+            },
+            AppEvent::StreamChunk {
+                content: String::new(),
+                thread_id: None,
+            },
+            AppEvent::Status {
+                message: String::new(),
+                thread_id: None,
+            },
+            AppEvent::JobStarted {
+                job_id: String::new(),
+                title: String::new(),
+                browse_url: String::new(),
+            },
+            AppEvent::ApprovalNeeded {
+                request_id: String::new(),
+                tool_name: String::new(),
+                description: String::new(),
+                parameters: String::new(),
+                thread_id: None,
+                allow_always: false,
+            },
+            AppEvent::AuthRequired {
+                extension_name: String::new(),
+                instructions: None,
+                auth_url: None,
+                setup_url: None,
+            },
+            AppEvent::AuthCompleted {
+                extension_name: String::new(),
+                success: true,
+                message: String::new(),
+            },
+            AppEvent::Error {
+                message: String::new(),
+                thread_id: None,
+            },
+            AppEvent::Heartbeat,
+            AppEvent::JobMessage {
+                job_id: String::new(),
+                role: String::new(),
+                content: String::new(),
+            },
+            AppEvent::JobToolUse {
+                job_id: String::new(),
+                tool_name: String::new(),
+                input: serde_json::Value::Null,
+            },
+            AppEvent::JobToolResult {
+                job_id: String::new(),
+                tool_name: String::new(),
+                output: String::new(),
+            },
+            AppEvent::JobStatus {
+                job_id: String::new(),
+                message: String::new(),
+            },
+            AppEvent::JobResult {
+                job_id: String::new(),
+                status: String::new(),
+                session_id: None,
+                fallback_deliverable: None,
+            },
+            AppEvent::ImageGenerated {
+                data_url: String::new(),
+                path: None,
+                thread_id: None,
+            },
+            AppEvent::Suggestions {
+                suggestions: vec![],
+                thread_id: None,
+            },
+            AppEvent::TurnCost {
+                input_tokens: 0,
+                output_tokens: 0,
+                cost_usd: String::new(),
+                thread_id: None,
+            },
+            AppEvent::ExtensionStatus {
+                extension_name: String::new(),
+                status: String::new(),
+                message: None,
+            },
+            AppEvent::ReasoningUpdate {
+                narrative: String::new(),
+                decisions: vec![],
+                thread_id: None,
+            },
+            AppEvent::JobReasoning {
+                job_id: String::new(),
+                narrative: String::new(),
+                decisions: vec![],
+            },
+        ];
+
+        for variant in &variants {
+            let json: serde_json::Value = serde_json::to_value(variant).unwrap();
+            let serde_type = json["type"].as_str().unwrap();
+            assert_eq!(
+                variant.event_type(),
+                serde_type,
+                "event_type() mismatch for variant: {:?}",
+                variant
+            );
+        }
+    }
+
+    #[test]
+    fn round_trip_deserialize() {
+        let original = AppEvent::Response {
+            content: "hello".to_string(),
+            thread_id: "t1".to_string(),
+        };
+        let json = serde_json::to_string(&original).unwrap();
+        let deserialized: AppEvent = serde_json::from_str(&json).unwrap();
+        assert_eq!(deserialized.event_type(), "response");
+    }
+}
@@ -0,0 +1,7 @@
+//! Shared types and utilities for the IronClaw workspace.
+
+mod event;
+mod util;
+
+pub use event::{AppEvent, ToolDecisionDto};
+pub use util::truncate_preview;
@@ -0,0 +1,100 @@
+//! Shared utility functions.
+
+/// 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 {
+    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
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn test_truncate_preview_short_string() {
+        assert_eq!(truncate_preview("hello", 10), "hello");
+    }
+
+    #[test]
+    fn test_truncate_preview_exact_boundary() {
+        assert_eq!(truncate_preview("hello", 5), "hello");
+    }
+
+    #[test]
+    fn test_truncate_preview_truncates_ascii() {
+        assert_eq!(truncate_preview("hello world", 5), "hello...");
+    }
+
+    #[test]
+    fn test_truncate_preview_empty_string() {
+        assert_eq!(truncate_preview("", 10), "");
+    }
+
+    #[test]
+    fn test_truncate_preview_multibyte_char_boundary() {
+        let s = "a\u{20AC}b";
+        let result = truncate_preview(s, 3);
+        assert_eq!(result, "a...");
+    }
+
+    #[test]
+    fn test_truncate_preview_emoji() {
+        let s = "hi\u{1F980}";
+        let result = truncate_preview(s, 4);
+        assert_eq!(result, "hi...");
+    }
+
+    #[test]
+    fn test_truncate_preview_cjk() {
+        let s = "\u{4F60}\u{597D}\u{4E16}\u{754C}";
+        let result = truncate_preview(s, 7);
+        assert_eq!(result, "\u{4F60}\u{597D}...");
+    }
+
+    #[test]
+    fn test_truncate_preview_zero_max_bytes() {
+        assert_eq!(truncate_preview("hello", 0), "...");
+    }
+
+    #[test]
+    fn test_truncate_preview_closes_tool_output_tag() {
+        let s = "<tool_output name=\"search\">\nSome very long content here\n</tool_output>";
+        let result = truncate_preview(s, 60);
+        assert!(result.ends_with("</tool_output>"));
+        assert!(result.contains("..."));
+    }
+
+    #[test]
+    fn test_truncate_preview_no_extra_close_when_intact() {
+        let s = "<tool_output name=\"echo\">\nshort\n</tool_output>";
+        let result = truncate_preview(s, 500);
+        assert_eq!(result, s);
+        assert_eq!(result.matches("</tool_output>").count(), 1);
+    }
+
+    #[test]
+    fn test_truncate_preview_non_xml_unaffected() {
+        let s = "Just a plain long string that gets truncated";
+        let result = truncate_preview(s, 10);
+        assert_eq!(result, "Just a pla...");
+        assert!(!result.contains("</tool_output>"));
+    }
+}
@@ -1,6 +1,6 @@
 [package]
 name = "ironclaw_safety"
-version = "0.1.0"
+version = "0.2.0"
 edition = "2024"
 rust-version = "1.92"
 description = "Prompt injection defense, input validation, secret leak detection, and safety policy enforcement"
@@ -8,7 +8,6 @@ authors = ["NEAR AI <[email protected]>"]
 license = "MIT OR Apache-2.0"
 homepage = "https://github.com/nearai/ironclaw"
 repository = "https://github.com/nearai/ironclaw"
-publish = false

 [package.metadata.dist]
 dist = false
@@ -0,0 +1,572 @@
+# User Management API
+
+DB-backed user management for multi-tenant IronClaw deployments. Covers admin user CRUD, per-user secrets provisioning, self-service profile, API token management, and usage reporting.
+
+## Authentication
+
+All endpoints require `Authorization: Bearer <token>`. Tokens are either:
+- **Env-var tokens** — configured via `GATEWAY_AUTH_TOKEN` (single-user) at startup
+- **DB-backed tokens** — created via `POST /api/tokens` or `POST /api/admin/users`
+
+DB tokens are SHA-256 hashed at rest; plaintext is returned exactly once at creation time.
+
+Auth is cached in a bounded LRU (1024 entries, 60s TTL). Suspending a user or revoking a token may take up to 60s to take effect.
+
+## Roles
+
+| Role | Scope |
+|------|-------|
+| `admin` | Full access to all endpoints |
+| `member` | Self-service profile + own token management only |
+
+Endpoints marked **Admin** return `403 Forbidden` for `member` role.
+
+---
+
+## Admin: Users
+
+### POST /api/admin/users
+
+Create a new user. Returns the user record and a one-time plaintext API token.
+
+**Auth:** Admin
+
+**Request body:**
+
+```json
+{
+  "display_name": "Alice Smith",
+  "email": "[email protected]",
+  "role": "member"
+}
+```
+
+| Field | Type | Required | Default | Notes |
+|-------|------|----------|---------|-------|
+| `display_name` | string | yes | | |
+| `email` | string | no | `null` | Must be unique if provided |
+| `role` | string | no | `"member"` | `"admin"` or `"member"` |
+
+**Response:** `200 OK`
+
+```json
+{
+  "id": "550e8400-e29b-41d4-a716-446655440000",
+  "email": "[email protected]",
+  "display_name": "Alice Smith",
+  "status": "active",
+  "role": "member",
+  "token": "a1b2c3d4e5f6...64-char hex...",
+  "created_at": "2026-03-25T12:00:00+00:00",
+  "created_by": "admin-user-id"
+}
+```
+
+The `token` field is the plaintext API token. It is shown **only once** — store it securely.
+
+**Errors:** `400` (missing display_name, invalid role), `403` (not admin), `503` (no database)
+
+---
+
+### GET /api/admin/users
+
+List all users.
+
+**Auth:** Admin
+
+**Response:** `200 OK`
+
+```json
+{
+  "users": [
+    {
+      "id": "550e8400-...",
+      "email": "[email protected]",
+      "display_name": "Alice Smith",
+      "status": "active",
+      "role": "member",
+      "created_at": "2026-03-25T12:00:00+00:00",
+      "updated_at": "2026-03-25T12:00:00+00:00",
+      "last_login_at": "2026-03-25T14:30:00+00:00",
+      "created_by": "admin-user-id"
+    }
+  ]
+}
+```
+
+---
+
+### GET /api/admin/users/{id}
+
+Get a single user by ID.
+
+**Auth:** Admin
+
+**Response:** `200 OK`
+
+```json
+{
+  "id": "550e8400-...",
+  "email": "[email protected]",
+  "display_name": "Alice Smith",
+  "status": "active",
+  "role": "member",
+  "created_at": "2026-03-25T12:00:00+00:00",
+  "updated_at": "2026-03-25T12:00:00+00:00",
+  "last_login_at": "2026-03-25T14:30:00+00:00",
+  "created_by": "admin-user-id",
+  "metadata": {}
+}
+```
+
+**Errors:** `404` (user not found), `403` (not admin)
+
+---
+
+### PATCH /api/admin/users/{id}
+
+Update a user's display name and/or metadata. Omitted fields are left unchanged.
+
+**Auth:** Admin
+
+**Request body:**
+
+```json
+{
+  "display_name": "Alice Johnson",
+  "metadata": {"department": "engineering"}
+}
+```
+
+| Field | Type | Required | Notes |
+|-------|------|----------|-------|
+| `display_name` | string | no | |
+| `role` | string | no | `"admin"` or `"member"` |
+| `metadata` | object | no | Replaces entire metadata object (full replacement; keys not included are removed) |
+
+**Response:** `200 OK` — returns the full updated user record (same shape as GET detail, without `last_login_at`/`created_by`).
+
+**Errors:** `404` (user not found), `403` (not admin)
+
+---
+
+### POST /api/admin/users/{id}/suspend
+
+Suspend a user. Suspended users cannot authenticate (DB auth checks user status).
+
+**Auth:** Admin
+
+**Response:** `200 OK`
+
+```json
+{
+  "id": "550e8400-...",
+  "status": "suspended"
+}
+```
+
+**Errors:** `404` (user not found), `403` (not admin)
+
+---
+
+### POST /api/admin/users/{id}/activate
+
+Re-activate a suspended user.
+
+**Auth:** Admin
+
+**Response:** `200 OK`
+
+```json
+{
+  "id": "550e8400-...",
+  "status": "active"
+}
+```
+
+**Errors:** `404` (user not found), `403` (not admin)
+
+---
+
+### DELETE /api/admin/users/{id}
+
+Permanently delete a user and all associated data (tokens, jobs, conversations, memory, routines, settings, secrets).
+
+**Auth:** Admin
+
+**Response:** `200 OK`
+
+```json
+{
+  "id": "550e8400-...",
+  "deleted": true
+}
+```
+
+**Errors:** `404` (user not found), `403` (not admin)
+
+**Cascade:** Deletes from `api_tokens`, `agent_jobs`, `conversations`, `memory_documents`, `routines`, `secrets`, `settings`, `wasm_tools`, and related tables. On PostgreSQL this uses FK cascades; on libSQL it uses explicit deletes.
+
+---
+
+## Admin: Per-User Secrets
+
+Provision secrets on behalf of individual users. The primary use case is an application backend (acting as admin) that configures per-user credentials so each user's IronClaw agent can call back to external services.
+
+Secrets are encrypted at rest with AES-256-GCM using a per-secret HKDF-derived key. Plaintext values are **never returned** by any endpoint — they can only be used by the agent's tool system at runtime.
+
+### PUT /api/admin/users/{user_id}/secrets/{name}
+
+Create or update a secret for the specified user. If a secret with the same name already exists, it is overwritten.
+
+**Auth:** Admin
+
+**Path parameters:**
+
+| Param | Type | Notes |
+|-------|------|-------|
+| `user_id` | string | The user's ID |
+| `name` | string | Secret name (normalized to lowercase) |
+
+**Request body:**
+
+```json
+{
+  "value": "sk-live-abc123...",
+  "provider": "my-app-backend",
+  "expires_in_days": 90
+}
+```
+
+| Field | Type | Required | Notes |
+|-------|------|----------|-------|
+| `value` | string | yes | The secret value (encrypted at rest, never returned) |
+| `provider` | string | no | Tag for grouping (e.g. `"stripe"`, `"my-app"`) |
+| `expires_in_days` | integer | no | Auto-expire after N days; `null` = never |
+
+**Response:** `200 OK`
+
+```json
+{
+  "user_id": "550e8400-...",
+  "name": "my_app_callback_token",
+  "status": "created"
+}
+```
+
+**Errors:** `400` (missing value), `403` (not admin), `503` (secrets store not available)
+
+**Example — application backend provisioning a callback token:**
+
+```bash
+# Admin creates a user
+curl -X POST https://ironclaw.example.com/api/admin/users \
+  -H "Authorization: Bearer $ADMIN_TOKEN" \
+  -d '{"display_name": "Alice", "role": "member"}'
+# Response includes: {"id": "alice-uuid", "token": "alice-bearer-token", ...}
+
+# Admin provisions a per-user callback secret
+curl -X PUT https://ironclaw.example.com/api/admin/users/alice-uuid/secrets/app_callback_token \
+  -H "Authorization: Bearer $ADMIN_TOKEN" \
+  -d '{"value": "per-user-jwt-for-alice", "provider": "my-app"}'
+
+# Now Alice's IronClaw agent can use the "app_callback_token" secret
+# when calling tools that need to authenticate back to the app backend.
+```
+
+---
+
+### GET /api/admin/users/{user_id}/secrets
+
+List a user's secrets. Returns names and providers only — **never values or hashes**.
+
+**Auth:** Admin
+
+**Response:** `200 OK`
+
+```json
+{
+  "user_id": "550e8400-...",
+  "secrets": [
+    {"name": "app_callback_token", "provider": "my-app"},
+    {"name": "openai_api_key", "provider": "openai"}
+  ]
+}
+```
+
+---
+
+### DELETE /api/admin/users/{user_id}/secrets/{name}
+
+Delete a specific secret for a user.
+
+**Auth:** Admin
+
+**Response:** `200 OK`
+
+```json
+{
+  "user_id": "550e8400-...",
+  "name": "app_callback_token",
+  "deleted": true
+}
+```
+
+**Errors:** `404` (secret not found), `403` (not admin), `503` (secrets store not available)
+
+---
+
+## Admin: Usage
+
+### GET /api/admin/usage
+
+Per-user LLM usage statistics aggregated from `llm_calls` via `agent_jobs.user_id`.
+
+**Auth:** Admin
+
+**Query parameters:**
+
+| Param | Type | Default | Notes |
+|-------|------|---------|-------|
+| `user_id` | string | all users | Filter to a single user |
+| `period` | string | `"day"` | `"day"` (24h), `"week"` (7d), or `"month"` (30d) |
+
+**Response:** `200 OK`
+
+```json
+{
+  "period": "week",
+  "since": "2026-03-18T12:00:00+00:00",
+  "usage": [
+    {
+      "user_id": "alice-id",
+      "model": "claude-sonnet-4-5-20250514",
+      "call_count": 42,
+      "input_tokens": 150000,
+      "output_tokens": 30000,
+      "total_cost": "1.23"
+    }
+  ]
+}
+```
+
+---
+
+## Self-Service: Profile
+
+### GET /api/profile
+
+Get the authenticated user's own profile.
+
+**Auth:** Any authenticated user
+
+**Response:** `200 OK`
+
+```json
+{
+  "id": "550e8400-...",
+  "email": "[email protected]",
+  "display_name": "Alice Smith",
+  "status": "active",
+  "role": "member",
+  "created_at": "2026-03-25T12:00:00+00:00",
+  "last_login_at": "2026-03-25T14:30:00+00:00"
+}
+```
+
+---
+
+### PATCH /api/profile
+
+Update the authenticated user's own display name and/or metadata.
+
+**Auth:** Any authenticated user
+
+**Request body:**
+
+```json
+{
+  "display_name": "Alice Johnson",
+  "metadata": {"theme": "dark"}
+}
+```
+
+**Response:** `200 OK`
+
+```json
+{
+  "id": "550e8400-...",
+  "display_name": "Alice Johnson",
+  "updated": true
+}
+```
+
+---
+
+## Self-Service: Tokens
+
+### POST /api/tokens
+
+Create a new API token for the authenticated user. Admins can optionally create tokens for other users by including `user_id`.
+
+**Auth:** Any authenticated user
+
+**Request body:**
+
+```json
+{
+  "name": "CI pipeline",
+  "expires_in_days": 90,
+  "user_id": "other-user-id"
+}
+```
+
+| Field | Type | Required | Notes |
+|-------|------|----------|-------|
+| `name` | string | yes | Human-readable label |
+| `expires_in_days` | integer | no | `null` = never expires |
+| `user_id` | string | no | Admin-only; create token for another user |
+
+**Response:** `200 OK`
+
+```json
+{
+  "token": "a1b2c3d4...64-char hex...",
+  "id": "token-uuid",
+  "name": "CI pipeline",
+  "token_prefix": "a1b2c3d4",
+  "expires_at": "2026-06-23T12:00:00+00:00",
+  "created_at": "2026-03-25T12:00:00+00:00"
+}
+```
+
+The `token` field is shown **only once**.
+
+---
+
+### GET /api/tokens
+
+List the authenticated user's tokens. Token hashes are never returned.
+
+**Auth:** Any authenticated user
+
+**Response:** `200 OK`
+
+```json
+{
+  "tokens": [
+    {
+      "id": "token-uuid",
+      "name": "CI pipeline",
+      "token_prefix": "a1b2c3d4",
+      "expires_at": "2026-06-23T12:00:00+00:00",
+      "last_used_at": "2026-03-25T14:00:00+00:00",
+      "created_at": "2026-03-25T12:00:00+00:00",
+      "revoked_at": null
+    }
+  ]
+}
+```
+
+---
+
+### DELETE /api/tokens/{id}
+
+Revoke one of the authenticated user's tokens. Users can only revoke their own tokens.
+
+**Auth:** Any authenticated user
+
+**Path:** `id` — UUID of the token to revoke
+
+**Response:** `200 OK`
+
+```json
+{
+  "status": "revoked",
+  "id": "token-uuid"
+}
+```
+
+**Errors:** `400` (invalid UUID), `404` (token not found or belongs to another user)
+
+---
+
+## Error Format
+
+All error responses return a plain text body with the error message and the corresponding HTTP status code:
+
+| Code | Meaning |
+|------|---------|
+| `400` | Bad request (missing fields, invalid input) |
+| `401` | Missing or invalid bearer token |
+| `403` | Authenticated but insufficient role (member accessing admin endpoint) |
+| `404` | Resource not found |
+| `503` | Database or secrets store not available |
+| `500` | Internal server error |
+
+---
+
+## Security Model
+
+### Secrets Encryption
+
+- **Algorithm:** AES-256-GCM with per-secret HKDF-SHA256 derived keys
+- **Master key:** 32+ bytes, resolved from `SECRETS_MASTER_KEY` env var or OS keychain
+- **Storage format:** `nonce (12B) || ciphertext || tag (16B)` in `encrypted_value` column
+- **Per-secret salt:** 32 random bytes stored alongside the ciphertext
+- **Zero-exposure:** Plaintext never appears in logs, debug output, API responses, or LLM conversations
+
+### Auth Cache
+
+- Bounded LRU cache (1024 entries max)
+- 60-second TTL per entry
+- Suspending a user or revoking a token takes up to 60s to propagate
+
+---
+
+## Database Schema
+
+### users
+
+| Column | Type (PG / libSQL) | Notes |
+|--------|--------------------|-------|
+| `id` | `TEXT` / `TEXT` | Primary key; typically UUID v4 strings (bootstrap admin may use a custom ID) |
+| `email` | `TEXT UNIQUE` | Nullable |
+| `display_name` | `TEXT NOT NULL` | |
+| `status` | `TEXT NOT NULL` | `"active"` or `"suspended"` |
+| `role` | `TEXT NOT NULL` | `"admin"` or `"member"` |
+| `created_at` | `TIMESTAMPTZ` / `TEXT` | |
+| `updated_at` | `TIMESTAMPTZ` / `TEXT` | |
+| `last_login_at` | `TIMESTAMPTZ` / `TEXT` | Nullable |
+| `created_by` | `TEXT` | Nullable, references `users.id` |
+| `metadata` | `JSONB` / `TEXT` | Default `{}` |
+
+### api_tokens
+
+| Column | Type (PG / libSQL) | Notes |
+|--------|--------------------|-------|
+| `id` | `UUID` / `TEXT` | Primary key |
+| `user_id` | `TEXT NOT NULL` | FK to `users.id` (PG cascades; libSQL explicit cleanup) |
+| `token_hash` | `BYTEA` / `BLOB` | SHA-256 of hex-encoded plaintext |
+| `token_prefix` | `TEXT NOT NULL` | First 8 chars for identification |
+| `name` | `TEXT NOT NULL` | Human-readable label |
+| `expires_at` | `TIMESTAMPTZ` / `TEXT` | Nullable |
+| `last_used_at` | `TIMESTAMPTZ` / `TEXT` | Nullable |
+| `created_at` | `TIMESTAMPTZ` / `TEXT` | |
+| `revoked_at` | `TIMESTAMPTZ` / `TEXT` | Nullable; set on revocation |
+
+### secrets
+
+| Column | Type (PG / libSQL) | Notes |
+|--------|--------------------|-------|
+| `id` | `UUID` / `TEXT` | Primary key |
+| `user_id` | `TEXT NOT NULL` | Scoped to user |
+| `name` | `TEXT NOT NULL` | Unique per user (lowercase normalized) |
+| `encrypted_value` | `BYTEA` / `BLOB` | AES-256-GCM (nonce + ciphertext + tag) |
+| `key_salt` | `BYTEA` / `BLOB` | Per-secret HKDF salt |
+| `provider` | `TEXT` | Optional grouping tag |
+| `expires_at` | `TIMESTAMPTZ` / `TEXT` | Nullable |
+| `last_used_at` | `TIMESTAMPTZ` / `TEXT` | Audit: last injection time |
+| `usage_count` | `BIGINT` / `INTEGER` | Audit: total injections |
+| `created_at` | `TIMESTAMPTZ` / `TEXT` | |
+| `updated_at` | `TIMESTAMPTZ` / `TEXT` | |
@@ -0,0 +1,31 @@
+-- User management tables for multi-tenant deployments.
+--
+-- Replaces the static GATEWAY_USER_TOKENS env var with DB-backed
+-- user registration, API token management, and invitation flow.
+
+CREATE TABLE users (
+    id TEXT PRIMARY KEY,                        -- matches existing user_id pattern (string, not UUID)
+    email TEXT UNIQUE,                          -- nullable for token-only users
+    display_name TEXT NOT NULL,
+    status TEXT NOT NULL DEFAULT 'active',       -- active | suspended | deactivated
+    role TEXT NOT NULL DEFAULT 'member',          -- admin | member
+    created_at TIMESTAMPTZ NOT NULL DEFAULT NOW(),
+    updated_at TIMESTAMPTZ NOT NULL DEFAULT NOW(),
+    last_login_at TIMESTAMPTZ,
+    created_by TEXT REFERENCES users(id),       -- who invited this user (nullable for bootstrap)
+    metadata JSONB NOT NULL DEFAULT '{}'        -- extensible profile data
+);
+
+CREATE TABLE api_tokens (
+    id UUID PRIMARY KEY,
+    user_id TEXT NOT NULL REFERENCES users(id) ON DELETE CASCADE,
+    token_hash BYTEA NOT NULL,                  -- SHA-256 hash (never store plaintext)
+    token_prefix TEXT NOT NULL,                 -- first 8 hex chars for display
+    name TEXT NOT NULL,                         -- human label ("my-laptop", "ci-bot")
+    expires_at TIMESTAMPTZ,                     -- nullable = never expires
+    last_used_at TIMESTAMPTZ,
+    created_at TIMESTAMPTZ NOT NULL DEFAULT NOW(),
+    revoked_at TIMESTAMPTZ                      -- soft-revoke: set this instead of deleting
+);
+CREATE INDEX idx_api_tokens_user ON api_tokens(user_id);
+CREATE INDEX idx_api_tokens_hash ON api_tokens(token_hash);
@@ -2,7 +2,7 @@
  "name": "feishu",
  "display_name": "Feishu / Lark Channel",
  "kind": "channel",
-  "version": "0.1.1",
+  "version": "0.1.3",
  "wit_version": "0.3.0",
  "description": "Talk to your agent through a Feishu or Lark bot",
  "keywords": [
@@ -19,8 +19,8 @@
  },
  "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"
+      "sha256": "a66ff0dafb67d2216d8161bb7e96e724a94acb0ab993b85d2782d30412f8fe94",
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/channel-feishu-0.1.3-wasm32-wasip2.tar.gz"
    }
  },
  "auth_summary": {
@@ -18,8 +18,8 @@
  },
  "artifacts": {
    "wasm32-wasip2": {
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.19.0/channel-telegram-0.2.4-wasm32-wasip2.tar.gz",
-      "sha256": "a7cb300ec1c946831cfceaa95c1dc8f30d0f42a3924f3cb5de8098821573f4b8"
+      "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": "0.2.1",
+  "version": "0.2.2",
  "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/v0.19.0/tool-github-0.2.1-wasm32-wasip2.tar.gz",
-      "sha256": "92c530b3ad172e2372d819744b5233f1d8f65768e26eb5a6c213eba3ce1de758"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-github-0.2.2-wasm32-wasip2.tar.gz",
+      "sha256": "70b55af593193d8fa495c0f702ea23284d83a624124f8a5f7564916ec5032c3f"
    }
  },
  "auth_summary": {
@@ -2,7 +2,7 @@
  "name": "gmail",
  "display_name": "Gmail",
  "kind": "tool",
-  "version": "0.2.0",
+  "version": "0.2.1",
  "wit_version": "0.3.0",
  "description": "Read, send, and manage Gmail messages and threads",
  "keywords": [
@@ -18,8 +18,8 @@
  },
  "artifacts": {
    "wasm32-wasip2": {
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.18.0/gmail-0.2.0-wasm32-wasip2.tar.gz",
-      "sha256": "ee9574e02e92bc1d481f1310eb88afd99ee52bf6971074ab33bd76bf99b34b1d"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-gmail-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "79025b40ee70ce1120acc4320bae50da095d7afb0ef67bd56d99b064b72ea779"
    }
  },
  "auth_summary": {
@@ -2,7 +2,7 @@
  "name": "google-calendar",
  "display_name": "Google Calendar",
  "kind": "tool",
-  "version": "0.2.0",
+  "version": "0.2.1",
  "wit_version": "0.3.0",
  "description": "Create, read, update, and delete Google Calendar events",
  "keywords": [
@@ -18,8 +18,8 @@
  },
  "artifacts": {
    "wasm32-wasip2": {
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.18.0/google-calendar-0.2.0-wasm32-wasip2.tar.gz",
-      "sha256": "2fa47150ea222e787c122182ad6f4dfa2ffaf5fe490d05e8de887a76445f8d2d"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-google-calendar-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "86bcc075010b08f5ab2f98f504cec1c6c9e0ca144857d185cbecf72a11f504bf"
    }
  },
  "auth_summary": {
@@ -2,7 +2,7 @@
  "name": "google-docs",
  "display_name": "Google Docs",
  "kind": "tool",
-  "version": "0.2.0",
+  "version": "0.2.1",
  "wit_version": "0.3.0",
  "description": "Create and edit Google Docs documents",
  "keywords": [
@@ -18,8 +18,8 @@
  },
  "artifacts": {
    "wasm32-wasip2": {
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.18.0/google-docs-0.2.0-wasm32-wasip2.tar.gz",
-      "sha256": "40e134a1c1564f832ca861c3396895d4e33ec67b99313fc1f97baf8d971423a9"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-google-docs-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "39d476029764949498a53a6a223f9952b5f4df151be7b8b19bf3fe4d401a57cd"
    }
  },
  "auth_summary": {
@@ -2,7 +2,7 @@
  "name": "google-drive",
  "display_name": "Google Drive",
  "kind": "tool",
-  "version": "0.2.0",
+  "version": "0.2.1",
  "wit_version": "0.3.0",
  "description": "Upload, download, search, and manage Google Drive files and folders",
  "keywords": [
@@ -18,8 +18,8 @@
  },
  "artifacts": {
    "wasm32-wasip2": {
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.18.0/google-drive-0.2.0-wasm32-wasip2.tar.gz",
-      "sha256": "002a341a1d58125563a7c69561b26fbc2629b04ea723cade744102bdc0fbb71f"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-google-drive-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "6e9a700fab93865c852af718666af64c5b534ad6a419fb4b736e07740188f494"
    }
  },
  "auth_summary": {
@@ -2,7 +2,7 @@
  "name": "google-sheets",
  "display_name": "Google Sheets",
  "kind": "tool",
-  "version": "0.2.0",
+  "version": "0.2.1",
  "wit_version": "0.3.0",
  "description": "Read and write Google Sheets spreadsheet data",
  "keywords": [
@@ -18,8 +18,8 @@
  },
  "artifacts": {
    "wasm32-wasip2": {
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.18.0/google-sheets-0.2.0-wasm32-wasip2.tar.gz",
-      "sha256": "8aa2c9d52f033edea3a6c2311b0ec694ccb6d0a54ef07e94d72bf8be1ce8009a"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-google-sheets-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "1f8c381799a916be83263cac9d497d52946e21b1b588592a3a42ca94a73b7051"
    }
  },
  "auth_summary": {
@@ -2,7 +2,7 @@
  "name": "google-slides",
  "display_name": "Google Slides",
  "kind": "tool",
-  "version": "0.2.0",
+  "version": "0.2.1",
  "wit_version": "0.3.0",
  "description": "Create and edit Google Slides presentations",
  "keywords": [
@@ -17,8 +17,8 @@
  },
  "artifacts": {
    "wasm32-wasip2": {
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.18.0/google-slides-0.2.0-wasm32-wasip2.tar.gz",
-      "sha256": "e931a97d4fd0b0b938e464dc7c7f2be6ea6b4d1508f5ea3cd931d44db23f05f5"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-google-slides-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "e2528be5da02f1b8cfc8ee9b0cdd849516c53d412e2f75c6175b3bded7f512cb"
    }
  },
  "auth_summary": {
@@ -2,7 +2,7 @@
  "name": "llm-context",
  "display_name": "LLM Context",
  "kind": "tool",
-  "version": "0.1.0",
+  "version": "0.1.1",
  "wit_version": "0.3.0",
  "description": "Fetch pre-extracted web content from Brave Search for grounding LLM answers (RAG, fact-checking)",
  "keywords": [
@@ -21,8 +21,8 @@
  },
  "artifacts": {
    "wasm32-wasip2": {
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.19.0/tool-llm-context-0.1.0-wasm32-wasip2.tar.gz",
-      "sha256": "d9ced2b1226b879135891e0ee40e072c7c95412e1b2462925a23853e1f92497e"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-llm-context-0.1.1-wasm32-wasip2.tar.gz",
+      "sha256": "9b19e2fd05dbbbe3c8bd55309a91db09124e8415eb0f767828b6e10b55771e63"
    }
  },
  "auth_summary": {
@@ -2,7 +2,7 @@
  "name": "slack-tool",
  "display_name": "Slack Tool",
  "kind": "tool",
-  "version": "0.2.0",
+  "version": "0.2.1",
  "wit_version": "0.3.0",
  "description": "Your agent uses Slack to post and read messages in your workspace",
  "keywords": [
@@ -17,8 +17,8 @@
  },
  "artifacts": {
    "wasm32-wasip2": {
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.19.0/tool-slack-0.2.0-wasm32-wasip2.tar.gz",
-      "sha256": "ccfb0415d7a04f9497726c712d15216de36e86f498b849101283c017f5ab4efb"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-slack-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "927519e5b7734beeb022d3b8bbd152e0e6b9f67c9452a8ad47809d3c4221a137"
    }
  },
  "auth_summary": {
@@ -2,7 +2,7 @@
  "name": "telegram-mtproto",
  "display_name": "Telegram Tool",
  "kind": "tool",
-  "version": "0.2.0",
+  "version": "0.2.1",
  "wit_version": "0.3.0",
  "description": "Your agent uses your Telegram account to read and send messages",
  "keywords": [
@@ -18,8 +18,8 @@
  },
  "artifacts": {
    "wasm32-wasip2": {
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.19.0/tool-telegram-0.2.0-wasm32-wasip2.tar.gz",
-      "sha256": "c17065ca41fae5f2a7c43b36144686718cd310a2f22442313bb1aa82bbad0ae4"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-telegram-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "1e57d0755fc9c7b3ec013d079f30168898b484a6919f9edd105f0cd80131c1cd"
    }
  },
  "auth_summary": {
@@ -2,7 +2,7 @@
  "name": "web-search",
  "display_name": "Web Search",
  "kind": "tool",
-  "version": "0.2.1",
+  "version": "0.2.2",
  "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/v0.19.0/tool-web-search-0.2.1-wasm32-wasip2.tar.gz",
-      "sha256": "bad275ca4ec314adea5241d6b92c44ccf9cebcbca8e30ba2493cc0bcb4b57218"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-web-search-0.2.2-wasm32-wasip2.tar.gz",
+      "sha256": "47382b50c1ea7525b20d59dc02fab04e336d018665826c2f24710bdf460779ae"
    }
  },
  "auth_summary": {
@@ -1,7 +1,2 @@
 [workspace]
 git_release_enable = false
-
-[[package]]
-name = "ironclaw_safety"
-publish = false
-release = false
@@ -16,6 +16,7 @@ use crate::agent::context_monitor::ContextMonitor;
 use crate::agent::heartbeat::{spawn_heartbeat, spawn_multi_user_heartbeat};
 use crate::agent::routine_engine::{RoutineEngine, spawn_cron_ticker};
 use crate::agent::self_repair::{DefaultSelfRepair, RepairResult, SelfRepair};
+use crate::agent::session::ThreadState;
 use crate::agent::session_manager::SessionManager;
 use crate::agent::submission::{Submission, SubmissionParser, SubmissionResult};
 use crate::agent::{HeartbeatConfig as AgentHeartbeatConfig, Router, Scheduler, SchedulerDeps};
@@ -84,6 +85,15 @@ fn resolve_owner_scope_notification_user(
    trimmed_option(explicit_user).or_else(|| trimmed_option(owner_fallback))
 }

+fn is_single_message_repl(message: &IncomingMessage) -> bool {
+    message.channel == "repl"
+        && message
+            .metadata
+            .get("single_message_mode")
+            .and_then(|value| value.as_bool())
+            .unwrap_or(false)
+}
+
 async fn resolve_channel_notification_user(
    extension_manager: Option<&Arc<ExtensionManager>>,
    channel: Option<&str>,
@@ -172,6 +182,8 @@ pub struct AgentDeps {
    /// Resolved LLM backend identifier (e.g., "nearai", "openai", "groq").
    /// Used by `/model` persistence to determine which env var to update.
    pub llm_backend: String,
+    /// Per-tenant rate limiting registry (lazily creates rate state per user).
+    pub tenant_rates: Arc<crate::tenant::TenantRateRegistry>,
 }

 /// The main agent that coordinates all components.
@@ -234,7 +246,10 @@ impl Agent {
            SchedulerDeps {
                tools: deps.tools.clone(),
                extension_manager: deps.extension_manager.clone(),
-                store: deps.store.clone(),
+                store: deps
+                    .store
+                    .as_ref()
+                    .map(|db| crate::tenant::AdminScope::new(Arc::clone(db))),
                hooks: deps.hooks.clone(),
            },
        );
@@ -315,6 +330,62 @@ impl Agent {
        &self.deps.cost_guard
    }

+    /// Build a tenant-scoped execution context for the given user.
+    ///
+    /// This is the standard entry point for per-user operations. The returned
+    /// [`TenantCtx`] provides a [`TenantScope`] that auto-binds `user_id` on
+    /// every database operation and a per-user rate limiter.
+    pub(super) async fn tenant_ctx(&self, user_id: &str) -> crate::tenant::TenantCtx {
+        let rate = self.deps.tenant_rates.get_or_create(user_id).await;
+
+        let store = self
+            .deps
+            .store
+            .as_ref()
+            .map(|db| crate::tenant::TenantScope::new(user_id, Arc::clone(db)));
+
+        // Reuse the owner workspace if user matches, otherwise create per-user.
+        // Per-user workspaces are seeded on first creation so they get identity
+        // files and BOOTSTRAP.md (which triggers the onboarding greeting).
+        let workspace = match &self.deps.workspace {
+            Some(ws) if ws.user_id() == user_id => Some(Arc::clone(ws)),
+            _ => {
+                if let Some(db) = self.deps.store.as_ref() {
+                    let ws = Arc::new(Workspace::new_with_db(user_id, Arc::clone(db)));
+                    if let Err(e) = ws.seed_if_empty().await {
+                        tracing::warn!(
+                            user_id = user_id,
+                            "Failed to seed per-user workspace: {}",
+                            e
+                        );
+                    }
+                    Some(ws)
+                } else {
+                    None
+                }
+            }
+        };
+
+        crate::tenant::TenantCtx::new(
+            user_id,
+            store,
+            workspace,
+            Arc::clone(&self.deps.cost_guard),
+            rate,
+        )
+    }
+
+    /// Get an admin-scoped database accessor for cross-tenant operations.
+    ///
+    /// Only for system-level components (heartbeat, routine engine, self-repair,
+    /// scheduler). Handler code should use [`tenant_ctx()`](Self::tenant_ctx) instead.
+    pub(super) fn admin_store(&self) -> Option<crate::tenant::AdminScope> {
+        self.deps
+            .store
+            .as_ref()
+            .map(|db| crate::tenant::AdminScope::new(Arc::clone(db)))
+    }
+
    pub(super) fn skill_registry(&self) -> Option<&Arc<std::sync::RwLock<SkillRegistry>>> {
        self.deps.skill_registry.as_ref()
    }
@@ -400,8 +471,8 @@ impl Agent {
            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(admin) = self.admin_store() {
+            self_repair = self_repair.with_store(admin);
        }
        if let Some(ref builder) = self.deps.builder {
            self_repair = self_repair.with_builder(Arc::clone(builder), Arc::clone(self.tools()));
@@ -538,30 +609,52 @@ impl Agent {
                    .await;
                    let notify_user = heartbeat_notify_user;
                    let channels = self.channels.clone();
+                    let is_multi_tenant = hb_config.multi_tenant;
                    tokio::spawn(async move {
                        while let Some(response) = notify_rx.recv().await {
+                            // In multi-tenant mode, extract the owning user_id from
+                            // the response metadata so notifications reach the
+                            // correct user rather than the agent's owner.
+                            // This intentionally overrides the configured notify_target
+                            // because each user's heartbeat should notify that user.
+                            let effective_user = if is_multi_tenant {
+                                response
+                                    .metadata
+                                    .get("owner_id")
+                                    .and_then(|v| v.as_str())
+                                    .map(String::from)
+                            } else {
+                                None
+                            };
+
                            // Try the configured channel first, fall back to
                            // broadcasting on all channels.
-                            let targeted_ok = if let Some(ref channel) = notify_channel
-                                && let Some(ref user) = notify_target
-                            {
-                                channels
-                                    .broadcast(channel, user, response.clone())
-                                    .await
-                                    .is_ok()
+                            let targeted_ok = if let Some(ref channel) = notify_channel {
+                                let target = effective_user.as_deref().or(notify_target.as_deref());
+                                if let Some(user) = target {
+                                    channels
+                                        .broadcast(channel, user, response.clone())
+                                        .await
+                                        .is_ok()
+                                } else {
+                                    false
+                                }
                            } else {
                                false
                            };

-                            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 {
-                                        tracing::warn!(
-                                            "Failed to broadcast heartbeat to {}: {}",
-                                            ch,
-                                            e
-                                        );
+                            if !targeted_ok {
+                                let fallback = effective_user.as_deref().or(notify_user.as_deref());
+                                if let Some(user) = fallback {
+                                    let results = channels.broadcast_all(user, response).await;
+                                    for (ch, result) in results {
+                                        if let Err(e) = result {
+                                            tracing::warn!(
+                                                "Failed to broadcast heartbeat to {}: {}",
+                                                ch,
+                                                e
+                                            );
+                                        }
                                    }
                                }
                            }
@@ -575,13 +668,13 @@ impl Agent {
                        .unwrap_or_default();

                    if config.multi_tenant {
-                        if let Some(store) = self.store() {
+                        if let Some(admin) = self.admin_store() {
                            Some(spawn_multi_user_heartbeat(
                                config,
                                hygiene,
                                self.cheap_llm().clone(),
                                Some(notify_tx),
-                                Arc::clone(store),
+                                admin,
                            ))
                        } else {
                            tracing::warn!("Multi-tenant heartbeat requires a database store");
@@ -594,7 +687,7 @@ impl Agent {
                            workspace.clone(),
                            self.cheap_llm().clone(),
                            Some(notify_tx),
-                            self.store().map(Arc::clone),
+                            self.admin_store(),
                        ))
                    }
                } else {
@@ -618,7 +711,7 @@ impl Agent {

                    let engine = Arc::new(RoutineEngine::new(
                        rt_config.clone(),
-                        Arc::clone(store),
+                        crate::tenant::AdminScope::new(Arc::clone(store)),
                        self.llm().clone(),
                        Arc::clone(workspace),
                        notify_tx,
@@ -1071,10 +1164,11 @@ impl Agent {
            } else {
                drop(sess);
                self.session_manager
-                    .resolve_thread(
+                    .resolve_thread_with_parsed_uuid(
                        &message.user_id,
                        &message.channel,
                        message.conversation_scope(),
+                        approval_thread_uuid,
                    )
                    .await
            }
@@ -1155,9 +1249,14 @@ impl Agent {
            && 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;
+            let single_message_repl = is_single_message_repl(message);
+            // Use post-hook content so that BeforeInbound hooks that rewrite
+            // input are respected by event trigger matching.
+            let fired = if single_message_repl {
+                engine.check_event_triggers_and_wait(message, content).await
+            } else {
+                engine.check_event_triggers(message, content).await
+            };
            if fired > 0 {
                tracing::debug!(
                    channel = %message.channel,
@@ -1165,15 +1264,58 @@ impl Agent {
                    fired,
                    "Consumed inbound user message with matching event-triggered routine(s)"
                );
-                return Ok(Some(String::new()));
+                return if single_message_repl {
+                    Ok(None)
+                } else {
+                    Ok(Some(String::new()))
+                };
            }
        }

+        // Build per-tenant execution context once; threaded through all handlers.
+        let tenant = self.tenant_ctx(&message.user_id).await;
+
+        // Per-user bootstrap: if this user's workspace was just seeded (fresh),
+        // persist the static greeting to their assistant conversation and
+        // broadcast it so the web client shows it immediately.
+        if tenant
+            .workspace()
+            .is_some_and(|ws| ws.take_bootstrap_pending())
+        {
+            tracing::info!(
+                user_id = message.user_id,
+                "Fresh user workspace — persisting bootstrap greeting"
+            );
+            if let Some(store) = tenant.store()
+                && let Ok(conv_id) = store
+                    .get_or_create_assistant_conversation(&message.channel)
+                    .await
+            {
+                let _ = store
+                    .add_conversation_message(conv_id, "assistant", BOOTSTRAP_GREETING)
+                    .await;
+                let mut out = OutgoingResponse::text(BOOTSTRAP_GREETING.to_string());
+                out.thread_id = Some(conv_id.to_string());
+                let _ = self
+                    .channels
+                    .broadcast(&message.channel, &message.user_id, out)
+                    .await;
+            }
+        }
+
+        let session_for_empty_exit = Arc::clone(&session);
+
        // Process based on submission type
        let result = match submission {
            Submission::UserInput { content } => {
                let mut result = self
-                    .process_user_input(message, session.clone(), thread_id, &content)
+                    .process_user_input(
+                        message,
+                        tenant.clone(),
+                        session.clone(),
+                        thread_id,
+                        &content,
+                    )
                    .await;

                // Drain any messages queued during processing.
@@ -1240,7 +1382,13 @@ impl Agent {
                    let mut queued_msg = message.clone();
                    queued_msg.attachments.clear();
                    result = self
-                        .process_user_input(&queued_msg, session.clone(), thread_id, &next_content)
+                        .process_user_input(
+                            &queued_msg,
+                            tenant.clone(),
+                            session.clone(),
+                            thread_id,
+                            &next_content,
+                        )
                        .await;

                    // If processing failed, re-queue the drained content so it
@@ -1265,8 +1413,30 @@ impl Agent {
                    command,
                    message.channel
                );
+                // /reasoning is special-cased here (not in handle_system_command)
+                // because it needs the session + thread_id to read turn reasoning
+                // data, which handle_system_command's signature doesn't provide.
+                if command == "reasoning" {
+                    let result = self
+                        .handle_reasoning_command(&args, &session, thread_id)
+                        .await;
+                    return match result {
+                        SubmissionResult::Response { content } => Ok(Some(content)),
+                        SubmissionResult::Ok { message } => Ok(message),
+                        SubmissionResult::Error { message } => {
+                            Ok(Some(format!("Error: {}", message)))
+                        }
+                        _ => {
+                            if is_single_message_repl(message) {
+                                Ok(None)
+                            } else {
+                                Ok(Some(String::new()))
+                            }
+                        }
+                    };
+                }
                // Authorization checks (including restart channel check) are enforced in handle_system_command
-                self.handle_system_command(&command, &args, &message.channel)
+                self.handle_system_command(&command, &args, &message.channel, &tenant)
                    .await
            }
            Submission::Undo => self.process_undo(session, thread_id).await,
@@ -1279,12 +1449,9 @@ impl Agent {
            Submission::Summarize => self.process_summarize(session, thread_id).await,
            Submission::Suggest => self.process_suggest(session, thread_id).await,
            Submission::JobStatus { job_id } => {
-                self.process_job_status(&message.user_id, job_id.as_deref())
-                    .await
-            }
-            Submission::JobCancel { job_id } => {
-                self.process_job_cancel(&message.user_id, &job_id).await
+                self.process_job_status(&tenant, job_id.as_deref()).await
            }
+            Submission::JobCancel { job_id } => self.process_job_cancel(&tenant, &job_id).await,
            Submission::Quit => return Ok(None),
            Submission::SwitchThread { thread_id: target } => {
                self.process_switch_thread(message, target).await
@@ -1324,7 +1491,26 @@ impl Agent {
                    Ok(Some(content))
                }
            }
-            SubmissionResult::Ok { message } => Ok(message),
+            SubmissionResult::Ok {
+                message: output_message,
+            } => {
+                let should_exit =
+                    if output_message.as_deref() == Some("") && is_single_message_repl(message) {
+                        let sess = session_for_empty_exit.lock().await;
+                        sess.threads
+                            .get(&thread_id)
+                            .map(|thread| thread.state != ThreadState::AwaitingApproval)
+                            .unwrap_or(true)
+                    } else {
+                        false
+                    };
+
+                if should_exit {
+                    Ok(None)
+                } else {
+                    Ok(output_message)
+                }
+            }
            SubmissionResult::Error { message } => Ok(Some(format!("Error: {}", message))),
            SubmissionResult::Interrupted => Ok(Some("Interrupted.".into())),
            SubmissionResult::NeedApproval { .. } => {
@@ -1340,7 +1526,7 @@ impl Agent {
 #[cfg(test)]
 mod tests {
    use super::{
-        chat_tool_execution_metadata, resolve_routine_notification_user,
+        chat_tool_execution_metadata, is_single_message_repl, resolve_routine_notification_user,
        should_fallback_routine_notification, truncate_for_preview,
    };
    use crate::channels::IncomingMessage;
@@ -1502,4 +1688,17 @@ mod tests {

        assert!(should_fallback_routine_notification(&error)); // safety: test-only assertion
    }
+
+    #[test]
+    fn single_message_repl_detection_requires_repl_channel_and_metadata_flag() {
+        let repl = IncomingMessage::new("repl", "owner-scope", "hello")
+            .with_metadata(serde_json::json!({ "single_message_mode": true }));
+        let gateway = IncomingMessage::new("gateway", "owner-scope", "hello")
+            .with_metadata(serde_json::json!({ "single_message_mode": true }));
+        let plain_repl = IncomingMessage::new("repl", "owner-scope", "hello");
+
+        assert!(is_single_message_repl(&repl)); // safety: test-only assertion
+        assert!(!is_single_message_repl(&gateway)); // safety: test-only assertion
+        assert!(!is_single_message_repl(&plain_repl)); // safety: test-only assertion
+    }
 }
@@ -10,7 +10,7 @@ use std::borrow::Cow;

 use crate::agent::session::PendingApproval;
 use crate::error::Error;
-use crate::llm::{ChatMessage, Reasoning, ReasoningContext, RespondResult};
+use crate::llm::{ChatMessage, FinishReason, Reasoning, ReasoningContext, RespondResult};

 /// Signal from the delegate indicating how the loop should proceed.
 pub enum LoopSignal {
@@ -134,6 +134,9 @@ pub async fn run_agentic_loop(
    config: &AgenticLoopConfig,
 ) -> Result<LoopOutcome, Error> {
    let mut consecutive_tool_intent_nudges: u32 = 0;
+    // Accumulates across all iterations (not reset by text responses) so
+    // non-consecutive truncations still escalate to force_text.
+    let mut truncation_count: u32 = 0;

    for iteration in 1..=config.max_iterations {
        // Check for external signals (stop, cancellation, user messages)
@@ -215,7 +218,35 @@ pub async fn run_agentic_loop(
                tool_calls,
                content,
            } => {
+                // If the response was truncated, tool call parameters are likely
+                // incomplete. Discard them and tell the LLM to try a different
+                // approach rather than executing malformed tool calls.
+                if output.finish_reason == FinishReason::Length {
+                    truncation_count += 1;
+                    let names: Vec<&str> = tool_calls.iter().map(|tc| tc.name.as_str()).collect();
+                    tracing::warn!(
+                        iteration,
+                        tools = ?names,
+                        truncation_count,
+                        "Discarding truncated tool calls (finish_reason=Length)"
+                    );
+                    if let Some(ref text) = content {
+                        reason_ctx.messages.push(ChatMessage::assistant(text));
+                    }
+                    reason_ctx
+                        .messages
+                        .push(ChatMessage::user(crate::llm::TRUNCATED_TOOL_CALL_NOTICE));
+                    // After repeated truncations, force text-only mode so the LLM
+                    // stops attempting tool calls it can't fit in the output budget.
+                    if truncation_count >= 3 {
+                        reason_ctx.force_text = true;
+                    }
+                    delegate.after_iteration(iteration).await;
+                    continue;
+                }
+
                consecutive_tool_intent_nudges = 0;
+                truncation_count = 0;

                if let Some(outcome) = delegate
                    .execute_tool_calls(tool_calls, content, reason_ctx)
@@ -271,6 +302,7 @@ mod tests {
        RespondOutput {
            result: RespondResult::Text(text.to_string()),
            usage: zero_usage(),
+            finish_reason: FinishReason::Stop,
        }
    }

@@ -281,6 +313,7 @@ mod tests {
                content: None,
            },
            usage: zero_usage(),
+            finish_reason: FinishReason::ToolUse,
        }
    }

@@ -414,6 +447,7 @@ mod tests {
            id: "call_1".to_string(),
            name: "echo".to_string(),
            arguments: serde_json::json!({}),
+            reasoning: None,
        };
        let delegate = MockDelegate::new(vec![
            tool_calls_output(vec![tool_call]),
@@ -621,4 +655,95 @@ mod tests {
        let result = truncate_for_preview("café", 4);
        assert_eq!(result, "caf...");
    }
+
+    #[tokio::test]
+    async fn test_truncated_tool_calls_discarded_on_length() {
+        let truncated_tool_call = ToolCall {
+            id: "call_1".to_string(),
+            name: "memory_write".to_string(),
+            arguments: serde_json::json!({}), // empty — truncated
+            reasoning: None,
+        };
+        let truncated_output = RespondOutput {
+            result: RespondResult::ToolCalls {
+                tool_calls: vec![truncated_tool_call],
+                content: Some("I'll write the report.".to_string()),
+            },
+            usage: zero_usage(),
+            finish_reason: FinishReason::Length, // response was truncated
+        };
+        let delegate = MockDelegate::new(vec![truncated_output, text_output("Summarized it.")]);
+        let reasoning = stub_reasoning();
+        let mut ctx = ReasoningContext::new();
+        let config = AgenticLoopConfig {
+            max_iterations: 5,
+            ..Default::default()
+        };
+
+        let outcome = run_agentic_loop(&delegate, &reasoning, &mut ctx, &config)
+            .await
+            .unwrap();
+
+        // Tool calls should NOT have been executed
+        assert_eq!(delegate.tool_exec_count.load(Ordering::SeqCst), 0);
+        // The loop should have continued and returned the text response
+        assert!(matches!(outcome, LoopOutcome::Response(ref t) if t == "Summarized it."));
+        // A truncation notice should have been injected into context
+        assert!(
+            ctx.messages
+                .iter()
+                .any(|m| m.role == crate::llm::Role::User && m.content.contains("truncated")),
+            "Should inject truncation notice into context"
+        );
+        // The partial assistant content should have been preserved
+        assert!(
+            ctx.messages
+                .iter()
+                .any(|m| m.role == crate::llm::Role::Assistant
+                    && m.content.contains("write the report")),
+            "Should preserve partial assistant content"
+        );
+    }
+
+    #[tokio::test]
+    async fn test_repeated_truncations_force_text_mode() {
+        let make_truncated = || RespondOutput {
+            result: RespondResult::ToolCalls {
+                tool_calls: vec![ToolCall {
+                    id: "call_1".to_string(),
+                    name: "memory_write".to_string(),
+                    arguments: serde_json::json!({}),
+                    reasoning: None,
+                }],
+                content: None,
+            },
+            usage: zero_usage(),
+            finish_reason: FinishReason::Length,
+        };
+        // Three truncated responses, then a text response
+        let delegate = MockDelegate::new(vec![
+            make_truncated(),
+            make_truncated(),
+            make_truncated(),
+            text_output("Gave up on tool calls."),
+        ]);
+        let reasoning = stub_reasoning();
+        let mut ctx = ReasoningContext::new();
+        let config = AgenticLoopConfig {
+            max_iterations: 5,
+            ..Default::default()
+        };
+
+        let outcome = run_agentic_loop(&delegate, &reasoning, &mut ctx, &config)
+            .await
+            .unwrap();
+
+        assert!(matches!(outcome, LoopOutcome::Response(_)));
+        assert_eq!(delegate.tool_exec_count.load(Ordering::SeqCst), 0);
+        // After 3 truncations, force_text should be set
+        assert!(
+            ctx.force_text,
+            "Should escalate to force_text after repeated truncations"
+        );
+    }
 }
@@ -33,6 +33,7 @@ impl Agent {
        &self,
        intent: MessageIntent,
        message: &IncomingMessage,
+        tenant: &crate::tenant::TenantCtx,
    ) -> Result<SubmissionResult, Error> {
        // Send thinking status for non-trivial operations
        if let MessageIntent::CreateJob { .. } = &intent {
@@ -52,24 +53,18 @@ impl Agent {
                description,
                category,
            } => {
-                self.handle_create_job(&message.user_id, title, description, category)
+                self.handle_create_job(tenant, title, description, category)
                    .await?
            }
            MessageIntent::CheckJobStatus { job_id } => {
-                self.handle_check_status(&message.user_id, job_id).await?
-            }
-            MessageIntent::CancelJob { job_id } => {
-                self.handle_cancel_job(&message.user_id, &job_id).await?
-            }
-            MessageIntent::ListJobs { filter } => {
-                self.handle_list_jobs(&message.user_id, filter).await?
-            }
-            MessageIntent::HelpJob { job_id } => {
-                self.handle_help_job(&message.user_id, &job_id).await?
+                self.handle_check_status(tenant, job_id).await?
            }
+            MessageIntent::CancelJob { job_id } => self.handle_cancel_job(tenant, &job_id).await?,
+            MessageIntent::ListJobs { filter } => self.handle_list_jobs(tenant, filter).await?,
+            MessageIntent::HelpJob { job_id } => self.handle_help_job(tenant, &job_id).await?,
            MessageIntent::Command { command, args } => {
                match self
-                    .handle_command(&command, &args, &message.channel)
+                    .handle_command(&command, &args, &message.channel, tenant)
                    .await?
                {
                    Some(s) => s,
@@ -83,14 +78,14 @@ impl Agent {

    async fn handle_create_job(
        &self,
-        user_id: &str,
+        tenant: &crate::tenant::TenantCtx,
        title: String,
        description: String,
        category: Option<String>,
    ) -> Result<String, Error> {
        let job_id = self
            .scheduler
-            .dispatch_job(user_id, &title, &description, None)
+            .dispatch_job(tenant.user_id(), &title, &description, None)
            .await?;

        // Set the dedicated category field (not stored in metadata)
@@ -113,7 +108,7 @@ impl Agent {

    async fn handle_check_status(
        &self,
-        user_id: &str,
+        tenant: &crate::tenant::TenantCtx,
        job_id: Option<String>,
    ) -> Result<String, Error> {
        match job_id {
@@ -122,7 +117,8 @@ impl Agent {
                    .map_err(|_| crate::error::JobError::NotFound { id: Uuid::nil() })?;

                // Try DB first for persistent state, fall back to ContextManager.
-                if let Some(store) = self.store()
+                // TenantScope.get_job() auto-filters by ownership — no manual check needed.
+                if let Some(store) = tenant.store()
                    && let Ok(Some(ctx)) = store.get_job(uuid).await
                {
                    return Ok(format!(
@@ -138,7 +134,7 @@ impl Agent {
                }

                let ctx = self.context_manager.get_context(uuid).await?;
-                if ctx.user_id != user_id {
+                if ctx.user_id != tenant.user_id() {
                    return Err(crate::error::JobError::NotFound { id: uuid }.into());
                }

@@ -155,21 +151,22 @@ impl Agent {
            }
            None => {
                // Show summary from DB for consistency with Jobs tab.
-                if let Some(store) = self.store() {
+                // TenantScope methods auto-scope to user — no user_id parameter needed.
+                if let Some(store) = tenant.store() {
                    let mut total = 0;
                    let mut in_progress = 0;
                    let mut completed = 0;
                    let mut failed = 0;
                    let mut stuck = 0;

-                    if let Ok(s) = store.agent_job_summary_for_user(user_id).await {
+                    if let Ok(s) = store.agent_job_summary().await {
                        total += s.total;
                        in_progress += s.in_progress;
                        completed += s.completed;
                        failed += s.failed;
                        stuck += s.stuck;
                    }
-                    if let Ok(s) = store.sandbox_job_summary_for_user(user_id).await {
+                    if let Ok(s) = store.sandbox_job_summary().await {
                        total += s.total;
                        in_progress += s.running;
                        completed += s.completed;
@@ -183,7 +180,7 @@ impl Agent {
                }

                // Fallback to ContextManager if no DB.
-                let summary = self.context_manager.summary_for(user_id).await;
+                let summary = self.context_manager.summary_for(tenant.user_id()).await;
                Ok(format!(
                    "Jobs summary: Total: {} In Progress: {} Completed: {} Failed: {} Stuck: {}",
                    summary.total,
@@ -196,19 +193,24 @@ impl Agent {
        }
    }

-    async fn handle_cancel_job(&self, user_id: &str, job_id: &str) -> Result<String, Error> {
+    async fn handle_cancel_job(
+        &self,
+        tenant: &crate::tenant::TenantCtx,
+        job_id: &str,
+    ) -> Result<String, Error> {
        let uuid = Uuid::parse_str(job_id)
            .map_err(|_| crate::error::JobError::NotFound { id: Uuid::nil() })?;

        let ctx = self.context_manager.get_context(uuid).await?;
-        if ctx.user_id != user_id {
+        if ctx.user_id != tenant.user_id() {
            return Err(crate::error::JobError::NotFound { id: uuid }.into());
        }

        self.scheduler.stop(uuid).await?;

        // Also update DB so the Jobs tab reflects cancellation immediately.
-        if let Some(store) = self.store()
+        // Use TenantScope — ownership already verified above.
+        if let Some(store) = tenant.store()
            && let Err(e) = store
                .update_job_status(uuid, JobState::Cancelled, Some("Cancelled by user"))
                .await
@@ -221,19 +223,20 @@ impl Agent {

    async fn handle_list_jobs(
        &self,
-        user_id: &str,
+        tenant: &crate::tenant::TenantCtx,
        _filter: Option<String>,
    ) -> Result<String, Error> {
        // List from DB for consistency with Jobs tab.
-        if let Some(store) = self.store() {
-            let agent_jobs = match store.list_agent_jobs_for_user(user_id).await {
+        // TenantScope methods auto-scope to user.
+        if let Some(store) = tenant.store() {
+            let agent_jobs = match store.list_agent_jobs().await {
                Ok(jobs) => jobs,
                Err(e) => {
                    tracing::warn!("Failed to list agent jobs: {}", e);
                    Vec::new()
                }
            };
-            let sandbox_jobs = match store.list_sandbox_jobs_for_user(user_id).await {
+            let sandbox_jobs = match store.list_sandbox_jobs().await {
                Ok(jobs) => jobs,
                Err(e) => {
                    tracing::warn!("Failed to list sandbox jobs: {}", e);
@@ -256,7 +259,7 @@ impl Agent {
        }

        // Fallback to ContextManager if no DB.
-        let jobs = self.context_manager.all_jobs_for(user_id).await;
+        let jobs = self.context_manager.all_jobs_for(tenant.user_id()).await;
        if jobs.is_empty() {
            return Ok("No jobs found.".to_string());
        }
@@ -270,12 +273,16 @@ impl Agent {
        Ok(output)
    }

-    async fn handle_help_job(&self, user_id: &str, job_id: &str) -> Result<String, Error> {
+    async fn handle_help_job(
+        &self,
+        tenant: &crate::tenant::TenantCtx,
+        job_id: &str,
+    ) -> Result<String, Error> {
        let uuid = Uuid::parse_str(job_id)
            .map_err(|_| crate::error::JobError::NotFound { id: Uuid::nil() })?;

        let ctx = self.context_manager.get_context(uuid).await?;
-        if ctx.user_id != user_id {
+        if ctx.user_id != tenant.user_id() {
            return Err(crate::error::JobError::NotFound { id: uuid }.into());
        }

@@ -308,11 +315,11 @@ impl Agent {
    /// Show job status inline — either all jobs (no id) or a specific job.
    pub(super) async fn process_job_status(
        &self,
-        user_id: &str,
+        tenant: &crate::tenant::TenantCtx,
        job_id: Option<&str>,
    ) -> Result<SubmissionResult, Error> {
        match self
-            .handle_check_status(user_id, job_id.map(|s| s.to_string()))
+            .handle_check_status(tenant, job_id.map(|s| s.to_string()))
            .await
        {
            Ok(text) => Ok(SubmissionResult::response(text)),
@@ -323,10 +330,10 @@ impl Agent {
    /// Cancel a job by ID.
    pub(super) async fn process_job_cancel(
        &self,
-        user_id: &str,
+        tenant: &crate::tenant::TenantCtx,
        job_id: &str,
    ) -> Result<SubmissionResult, Error> {
-        match self.handle_cancel_job(user_id, job_id).await {
+        match self.handle_cancel_job(tenant, job_id).await {
            Ok(text) => Ok(SubmissionResult::response(text)),
            Err(e) => Ok(SubmissionResult::error(format!("Cancel error: {}", e))),
        }
@@ -465,12 +472,101 @@ impl Agent {
        }
    }

+    /// Handle `/reasoning [N|all]` — show reasoning history for the active thread.
+    pub(super) async fn handle_reasoning_command(
+        &self,
+        args: &[String],
+        session: &Arc<Mutex<Session>>,
+        thread_id: Uuid,
+    ) -> SubmissionResult {
+        // Clone the turn data we need, then drop the session lock.
+        let turns_snapshot: Vec<(
+            usize,
+            Option<String>,
+            Vec<crate::agent::session::TurnToolCall>,
+        )>;
+        {
+            let sess = session.lock().await;
+            let thread = match sess.threads.get(&thread_id) {
+                Some(t) => t,
+                None => return SubmissionResult::error("No active thread."),
+            };
+
+            if thread.turns.is_empty() {
+                return SubmissionResult::ok_with_message("No turns yet.");
+            }
+
+            // Parse argument: default=last turn, "all"=all turns, N=specific turn (1-based).
+            let selected: Vec<&crate::agent::session::Turn> = match args.first().map(|s| s.as_str())
+            {
+                Some("all") => thread.turns.iter().collect(),
+                Some(n) => match n.parse::<usize>() {
+                    Ok(0) => return SubmissionResult::error("Turn numbers start at 1."),
+                    Ok(num) if num > thread.turns.len() => {
+                        return SubmissionResult::error(format!(
+                            "Turn {} does not exist (max: {}).",
+                            num,
+                            thread.turns.len()
+                        ));
+                    }
+                    Ok(num) => vec![&thread.turns[num - 1]],
+                    Err(_) => return SubmissionResult::error("Usage: /reasoning [N|all]"),
+                },
+                None => {
+                    // Default: last turn that has tool calls
+                    match thread.turns.iter().rev().find(|t| !t.tool_calls.is_empty()) {
+                        Some(t) => vec![t],
+                        None => {
+                            return SubmissionResult::ok_with_message("No turns with tool calls.");
+                        }
+                    }
+                }
+            };
+
+            turns_snapshot = selected
+                .into_iter()
+                .map(|t| (t.turn_number, t.narrative.clone(), t.tool_calls.clone()))
+                .collect();
+        }
+        // Session lock is now dropped — format output without holding it.
+
+        let mut output = String::new();
+        for (turn_number, narrative, tool_calls) in &turns_snapshot {
+            output.push_str(&format!("--- Turn {} ---\n", turn_number + 1));
+            if let Some(narrative) = narrative {
+                output.push_str(&format!("Reasoning: {}\n", narrative));
+            }
+            if tool_calls.is_empty() {
+                output.push_str("  (no tool calls)\n");
+            } else {
+                for tc in tool_calls {
+                    let status = if tc.error.is_some() {
+                        "error"
+                    } else if tc.result.is_some() {
+                        "ok"
+                    } else {
+                        "pending"
+                    };
+                    output.push_str(&format!("  {} [{}]", tc.name, status));
+                    if let Some(ref rationale) = tc.rationale {
+                        output.push_str(&format!(" — {}", rationale));
+                    }
+                    output.push('\n');
+                }
+            }
+            output.push('\n');
+        }
+
+        SubmissionResult::response(output.trim_end())
+    }
+
    /// Handle system commands that bypass thread-state checks entirely.
    pub(super) async fn handle_system_command(
        &self,
        command: &str,
        args: &[String],
        channel: &str,
+        tenant: &crate::tenant::TenantCtx,
    ) -> Result<SubmissionResult, Error> {
        match command {
            "help" => Ok(SubmissionResult::response(concat!(
@@ -480,6 +576,7 @@ impl Agent {
                "  /version          Show version info\n",
                "  /tools            List available tools\n",
                "  /debug            Toggle debug mode\n",
+                "  /reasoning [N|all] Show agent reasoning for turns\n",
                "  /ping             Connectivity check\n",
                "\n",
                "Jobs:\n",
@@ -664,12 +761,12 @@ impl Agent {
                    }

                    if self.config.multi_tenant {
-                        // Multi-tenant: only persist to per-user settings.
+                        // Multi-tenant: only persist to per-user DB settings.
                        // Do NOT call set_model() on the shared provider — that
                        // would change the default for all users. The per-request
                        // model_override in the dispatcher reads from the same
                        // "selected_model" setting and applies it per-user.
-                        self.persist_selected_model(requested).await;
+                        self.persist_selected_model(tenant, requested).await;
                        Ok(SubmissionResult::response(format!(
                            "Model preference set to: {} (per-user)",
                            requested
@@ -678,7 +775,7 @@ impl Agent {
                        match self.llm().set_model(requested) {
                            Ok(()) => {
                                // Persist the model choice so it survives restarts.
-                                self.persist_selected_model(requested).await;
+                                self.persist_selected_model(tenant, requested).await;
                                Ok(SubmissionResult::response(format!(
                                    "Switched model to: {}",
                                    requested
@@ -830,10 +927,14 @@ impl Agent {
        command: &str,
        args: &[String],
        channel: &str,
+        tenant: &crate::tenant::TenantCtx,
    ) -> Result<Option<String>, Error> {
        // System commands are now handled directly via Submission::SystemCommand,
        // but the router may still send us unknown /commands.
-        match self.handle_system_command(command, args, channel).await? {
+        match self
+            .handle_system_command(command, args, channel, tenant)
+            .await?
+        {
            SubmissionResult::Response { content } => Ok(Some(content)),
            SubmissionResult::Ok { message } => Ok(message),
            SubmissionResult::Error { message } => Ok(Some(format!("Error: {}", message))),
@@ -845,23 +946,33 @@ impl Agent {
    ///
    /// Best-effort: logs warnings on failure but does not propagate errors,
    /// since the in-memory model switch already succeeded.
-    async fn persist_selected_model(&self, model: &str) {
-        // 1. Persist to DB if available.
-        if let Some(store) = self.store() {
+    ///
+    /// In multi-tenant mode, only the per-user DB setting is written — global
+    /// .env and TOML files are shared across users and must not be mutated.
+    async fn persist_selected_model(&self, tenant: &crate::tenant::TenantCtx, model: &str) {
+        // 1. Persist to DB if available (per-user scoped via TenantScope).
+        if let Some(store) = tenant.store() {
            let value = serde_json::Value::String(model.to_string());
-            if let Err(e) = store
-                .set_setting(self.owner_id(), "selected_model", &value)
-                .await
-            {
+            if let Err(e) = store.set_setting("selected_model", &value).await {
                tracing::warn!("Failed to persist model to DB: {}", e);
            } else {
-                tracing::debug!("Persisted selected_model to DB: {}", model);
+                tracing::debug!(
+                    user_id = tenant.user_id(),
+                    "Persisted selected_model to DB: {}",
+                    model
+                );
            }
        } else {
            tracing::warn!("No database store available — model choice will not persist to DB");
        }

-        // 2. Update .env and TOML config file (sync I/O in spawn_blocking).
+        // 2. In multi-tenant mode, skip .env/TOML writes — these are global
+        // files shared by all users. The per-user DB setting is sufficient.
+        if self.config.multi_tenant {
+            return;
+        }
+
+        // 3. Update .env and TOML config file (sync I/O in spawn_blocking).
        let model_owned = model.to_string();
        let backend = self.deps.llm_backend.clone();
        if let Err(e) = tokio::task::spawn_blocking(move || {
@@ -42,6 +42,7 @@ impl Agent {
    pub(super) async fn run_agentic_loop(
        &self,
        message: &IncomingMessage,
+        tenant: crate::tenant::TenantCtx,
        session: Arc<Mutex<Session>>,
        thread_id: Uuid,
        initial_messages: Vec<ChatMessage>,
@@ -63,7 +64,12 @@ impl Agent {
        );

        let system_prompt = if let Some(ws) = self.workspace() {
-            match ws
+            let scoped_workspace = if ws.user_id() == message.user_id {
+                Arc::clone(ws)
+            } else {
+                Arc::new(ws.scoped_to_user(&message.user_id))
+            };
+            match scoped_workspace
                .system_prompt_for_context_tz(is_group_chat, user_tz)
                .await
            {
@@ -163,6 +169,7 @@ impl Agent {

        let delegate = ChatDelegate {
            agent: self,
+            tenant,
            session: session.clone(),
            thread_id,
            message,
@@ -235,6 +242,7 @@ impl Agent {
 /// auth intercept, and cost tracking.
 struct ChatDelegate<'a> {
    agent: &'a Agent,
+    tenant: crate::tenant::TenantCtx,
    session: Arc<Mutex<Session>>,
    thread_id: Uuid,
    message: &'a IncomingMessage,
@@ -298,6 +306,8 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {

        // Update context for this iteration
        reason_ctx.available_tools = tool_defs;
+        // Preserve force_text if already set (e.g. by truncation escalation).
+        let force_text = force_text || reason_ctx.force_text;
        reason_ctx.system_prompt = Some(if force_text {
            self.cached_prompt_no_tools.clone()
        } else {
@@ -332,12 +342,7 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
        iteration: usize,
    ) -> Result<crate::llm::RespondOutput, Error> {
        // Enforce cost guardrails before the LLM call (global + per-user)
-        if let Err(limit) = self
-            .agent
-            .cost_guard()
-            .check_allowed_for_user(&self.message.user_id)
-            .await
-        {
+        if let Err(limit) = self.tenant.check_cost_allowed().await {
            return Err(crate::error::LlmError::InvalidResponse {
                provider: "agent".to_string(),
                reason: limit.to_string(),
@@ -348,12 +353,10 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
        // Apply per-user model override from settings (first iteration only
        // to avoid repeated DB lookups within the same agentic loop).
        // Uses "selected_model" — the same key the /model command persists to
-        // via SettingsStore (per-user scoped).
+        // via SettingsStore (per-user scoped via TenantScope).
        if iteration == 0
-            && let Some(store) = self.agent.store()
-            && let Ok(Some(value)) = store
-                .get_setting(&self.message.user_id, "selected_model")
-                .await
+            && let Some(store) = self.tenant.store()
+            && let Ok(Some(value)) = store.get_setting("selected_model").await
            && let Some(model) = value.as_str()
        {
            let model = model.trim();
@@ -397,18 +400,27 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
        };

        // Record cost and track token usage (global + per-user).
-        // Use the override model name if set so cost attribution is accurate.
-        let model_name = reason_ctx
-            .model_override
-            .clone()
-            .unwrap_or_else(|| self.agent.llm().active_model_name());
+        // Use the provider's effective_model_name so cost attribution matches
+        // the model that actually served the request. When the override is
+        // honoured (e.g. NearAI), this returns the override name; when the
+        // provider ignores overrides (e.g. Rig-based), it returns the active
+        // model, keeping attribution accurate in both cases.
+        let model_name = self
+            .agent
+            .llm()
+            .effective_model_name(reason_ctx.model_override.as_deref());
+        let cost_per_token = if reason_ctx.model_override.is_some() {
+            // Override may use different pricing; let CostGuard fall back to
+            // costs::model_cost() for the effective model.
+            None
+        } else {
+            Some(self.agent.llm().cost_per_token())
+        };
        let read_discount = self.agent.llm().cache_read_discount();
        let write_multiplier = self.agent.llm().cache_write_multiplier();
        let call_cost = self
-            .agent
-            .cost_guard()
-            .record_llm_call_for_user(
-                &self.message.user_id,
+            .tenant
+            .record_llm_call(
                &model_name,
                output.usage.input_tokens,
                output.usage.output_tokens,
@@ -416,7 +428,7 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
                output.usage.cache_creation_input_tokens,
                read_discount,
                write_multiplier,
-                Some(self.agent.llm().cost_per_token()),
+                cost_per_token,
            )
            .await;
        tracing::debug!(
@@ -426,6 +438,24 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
            call_cost,
        );

+        // Persist LLM call to DB so usage stats survive restarts.
+        // Chat turns don't create agent_jobs, so job_id is None.
+        if let Some(store) = self.tenant.store() {
+            let record = crate::history::LlmCallRecord {
+                job_id: None,
+                conversation_id: Some(self.thread_id),
+                provider: &self.agent.deps.llm_backend,
+                model: &model_name,
+                input_tokens: output.usage.input_tokens,
+                output_tokens: output.usage.output_tokens,
+                cost: call_cost,
+                purpose: Some("chat"),
+            };
+            if let Err(e) = store.record_llm_call(&record).await {
+                tracing::warn!("Failed to persist LLM call to DB: {}", e);
+            }
+        }
+
        Ok(output)
    }

@@ -447,6 +477,19 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
        content: Option<String>,
        reason_ctx: &mut ReasoningContext,
    ) -> Result<Option<LoopOutcome>, Error> {
+        // Extract and sanitize the narrative before consuming `content`.
+        let narrative = content
+            .as_deref()
+            .filter(|c| !c.trim().is_empty())
+            .map(|c| {
+                let sanitized = self
+                    .agent
+                    .safety()
+                    .sanitize_tool_output("agent_narrative", c);
+                sanitized.content
+            })
+            .filter(|c| !c.trim().is_empty());
+
        // Add the assistant message with tool_calls to context.
        // OpenAI protocol requires this before tool-result messages.
        reason_ctx
@@ -467,6 +510,41 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
            )
            .await;

+        // Build per-tool decisions for the reasoning update.
+        // Sanitize each rationale through SafetyLayer (parity with JobDelegate).
+        let decisions: Vec<crate::channels::ToolDecision> = tool_calls
+            .iter()
+            .filter_map(|tc| {
+                tc.reasoning.as_ref().map(|r| {
+                    let sanitized = self
+                        .agent
+                        .safety()
+                        .sanitize_tool_output("tool_rationale", r)
+                        .content;
+                    crate::channels::ToolDecision {
+                        tool_name: tc.name.clone(),
+                        rationale: sanitized,
+                    }
+                })
+            })
+            .collect();
+
+        // Emit reasoning update to channels.
+        if narrative.is_some() || !decisions.is_empty() {
+            let _ = self
+                .agent
+                .channels
+                .send_status(
+                    &self.message.channel,
+                    StatusUpdate::ReasoningUpdate {
+                        narrative: narrative.clone().unwrap_or_default(),
+                        decisions: decisions.clone(),
+                    },
+                    &self.message.metadata,
+                )
+                .await;
+        }
+
        // Record tool calls in the thread with sensitive params redacted.
        {
            let mut redacted_args: Vec<serde_json::Value> = Vec::with_capacity(tool_calls.len());
@@ -482,8 +560,23 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
            if let Some(thread) = sess.threads.get_mut(&self.thread_id)
                && let Some(turn) = thread.last_turn_mut()
            {
+                // Set turn-level narrative.
+                if turn.narrative.is_none() {
+                    turn.narrative = narrative;
+                }
                for (tc, safe_args) in tool_calls.iter().zip(redacted_args) {
-                    turn.record_tool_call(&tc.name, safe_args);
+                    let sanitized_rationale = tc.reasoning.as_ref().map(|r| {
+                        self.agent
+                            .safety()
+                            .sanitize_tool_output("tool_rationale", r)
+                            .content
+                    });
+                    turn.record_tool_call_with_reasoning(
+                        &tc.name,
+                        safe_args,
+                        sanitized_rationale,
+                        Some(tc.id.clone()),
+                    );
                }
            }
        }
@@ -755,7 +848,7 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
                        if let Some(thread) = sess.threads.get_mut(&self.thread_id)
                            && let Some(turn) = thread.last_turn_mut()
                        {
-                            turn.record_tool_error(result_content.clone());
+                            turn.record_tool_error_for(&tc.id, result_content.clone());
                        }
                    }
                    reason_ctx.messages.push(tool_message);
@@ -874,16 +967,19 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
                        &tool_result,
                    );

-                    // Record sanitized result in thread
+                    // Record sanitized result in thread (identity-based matching).
                    {
                        let mut sess = self.session.lock().await;
                        if let Some(thread) = sess.threads.get_mut(&self.thread_id)
                            && let Some(turn) = thread.last_turn_mut()
                        {
                            if is_tool_error {
-                                turn.record_tool_error(result_content.clone());
+                                turn.record_tool_error_for(&tc.id, result_content.clone());
                            } else {
-                                turn.record_tool_result(serde_json::json!(result_content));
+                                turn.record_tool_result_for(
+                                    &tc.id,
+                                    serde_json::json!(result_content),
+                                );
                            }
                        }
                    }
@@ -1267,6 +1363,7 @@ mod tests {
            sandbox_readiness: crate::agent::routine_engine::SandboxReadiness::DisabledByConfig,
            builder: None,
            llm_backend: "nearai".to_string(),
+            tenant_rates: Arc::new(crate::tenant::TenantRateRegistry::new(4, 3)),
        };

        Agent::new(
@@ -1286,8 +1383,11 @@ mod tests {
                max_tool_iterations: 50,
                auto_approve_tools: false,
                default_timezone: "UTC".to_string(),
+                max_jobs_per_user: None,
                max_tokens_per_job: 0,
                multi_tenant: false,
+                max_llm_concurrent_per_user: None,
+                max_jobs_concurrent_per_user: None,
            },
            deps,
            Arc::new(ChannelManager::new()),
@@ -1497,11 +1597,13 @@ mod tests {
                    id: "call_2".to_string(),
                    name: "http".to_string(),
                    arguments: serde_json::json!({"url": "https://example.com"}),
+                    reasoning: None,
                },
                ToolCall {
                    id: "call_3".to_string(),
                    name: "echo".to_string(),
                    arguments: serde_json::json!({"message": "done"}),
+                    reasoning: None,
                },
            ],
            user_timezone: None,
@@ -1687,6 +1789,7 @@ mod tests {
                    id: "call_1".to_string(),
                    name: "echo".to_string(),
                    arguments: serde_json::json!({"message": "hi"}),
+                    reasoning: None,
                }],
            ),
            ChatMessage::tool_result("call_1", "echo", "hi"),
@@ -1779,11 +1882,13 @@ mod tests {
                        id: "c1".to_string(),
                        name: "http".to_string(),
                        arguments: serde_json::json!({}),
+                        reasoning: None,
                    },
                    ToolCall {
                        id: "c2".to_string(),
                        name: "echo".to_string(),
                        arguments: serde_json::json!({}),
+                        reasoning: None,
                    },
                ],
            ),
@@ -1817,6 +1922,7 @@ mod tests {
                    id: "c1".to_string(),
                    name: "echo".to_string(),
                    arguments: serde_json::json!({}),
+                    reasoning: None,
                }],
            ),
            ChatMessage::tool_result("c1", "echo", "done"),
@@ -1947,6 +2053,7 @@ mod tests {
                    id: crate::llm::generate_tool_call_id(0, 0),
                    name: "echo".to_string(),
                    arguments: serde_json::json!({"message": "looping"}),
+                    reasoning: None,
                }],
                input_tokens: 0,
                output_tokens: 5,
@@ -2100,6 +2207,7 @@ mod tests {
                    id: crate::llm::generate_tool_call_id(0, 0),
                    name: "nonexistent_tool".to_string(),
                    arguments: serde_json::json!({}),
+                    reasoning: None,
                }],
                input_tokens: 0,
                output_tokens: 5,
@@ -2137,6 +2245,7 @@ mod tests {
            sandbox_readiness: crate::agent::routine_engine::SandboxReadiness::DisabledByConfig,
            builder: None,
            llm_backend: "nearai".to_string(),
+            tenant_rates: Arc::new(crate::tenant::TenantRateRegistry::new(4, 3)),
        };

        Agent::new(
@@ -2156,8 +2265,11 @@ mod tests {
                max_tool_iterations,
                auto_approve_tools: true,
                default_timezone: "UTC".to_string(),
+                max_jobs_per_user: None,
                max_tokens_per_job: 0,
                multi_tenant: false,
+                max_llm_concurrent_per_user: None,
+                max_jobs_concurrent_per_user: None,
            },
            deps,
            Arc::new(ChannelManager::new()),
@@ -2192,13 +2304,14 @@ mod tests {

        let message = IncomingMessage::new("test", "test-user", "do something");
        let initial_messages = vec![ChatMessage::user("do something")];
+        let tenant = agent.tenant_ctx("test-user").await;

        // The dispatcher must terminate within 5 seconds. If there is an
        // infinite loop bug (e.g., index not advancing on tool failure), the
        // timeout will fire and the test will fail.
        let result = tokio::time::timeout(
            Duration::from_secs(5),
-            agent.run_agentic_loop(&message, session, thread_id, initial_messages),
+            agent.run_agentic_loop(&message, tenant, session, thread_id, initial_messages),
        )
        .await;

@@ -2260,6 +2373,7 @@ mod tests {
                sandbox_readiness: crate::agent::routine_engine::SandboxReadiness::DisabledByConfig,
                builder: None,
                llm_backend: "nearai".to_string(),
+                tenant_rates: Arc::new(crate::tenant::TenantRateRegistry::new(4, 3)),
            };

            Agent::new(
@@ -2279,8 +2393,11 @@ mod tests {
                    max_tool_iterations: max_iter,
                    auto_approve_tools: true,
                    default_timezone: "UTC".to_string(),
+                    max_jobs_per_user: None,
                    max_tokens_per_job: 0,
                    multi_tenant: false,
+                    max_llm_concurrent_per_user: None,
+                    max_jobs_concurrent_per_user: None,
                },
                deps,
                Arc::new(ChannelManager::new()),
@@ -2300,13 +2417,14 @@ mod tests {

        let message = IncomingMessage::new("test", "test-user", "keep calling tools");
        let initial_messages = vec![ChatMessage::user("keep calling tools")];
+        let tenant = agent.tenant_ctx("test-user").await;

        // Even with an LLM that always wants to call tools, the dispatcher
        // must terminate within the timeout thanks to force_text at
        // max_tool_iterations.
        let result = tokio::time::timeout(
            Duration::from_secs(5),
-            agent.run_agentic_loop(&message, session, thread_id, initial_messages),
+            agent.run_agentic_loop(&message, tenant, session, thread_id, initial_messages),
        )
        .await;

@@ -31,8 +31,8 @@ use chrono_tz::Tz;
 use tokio::sync::mpsc;

 use crate::channels::OutgoingResponse;
-use crate::db::Database;
 use crate::llm::{ChatMessage, CompletionRequest, LlmProvider, Reasoning};
+use crate::tenant::AdminScope;
 use crate::workspace::Workspace;
 use crate::workspace::hygiene::HygieneConfig;

@@ -182,7 +182,7 @@ pub struct HeartbeatRunner {
    workspace: Arc<Workspace>,
    llm: Arc<dyn LlmProvider>,
    response_tx: Option<mpsc::Sender<OutgoingResponse>>,
-    store: Option<Arc<dyn Database>>,
+    store: Option<AdminScope>,
    consecutive_failures: u32,
 }

@@ -211,8 +211,8 @@ impl HeartbeatRunner {
        self
    }

-    /// Set the database store for persistent heartbeat conversations.
-    pub fn with_store(mut self, store: Arc<dyn Database>) -> Self {
+    /// Set the admin-scoped database store for persistent heartbeat conversations.
+    pub fn with_store(mut self, store: AdminScope) -> Self {
        self.store = Some(store);
        self
    }
@@ -400,7 +400,7 @@ impl HeartbeatRunner {
    }

    /// Send a notification about heartbeat findings.
-    pub(crate) async fn send_notification(&self, message: &str) {
+    async fn send_notification(&self, message: &str) {
        let Some(ref tx) = self.response_tx else {
            tracing::debug!("No response channel configured for heartbeat notifications");
            return;
@@ -497,7 +497,7 @@ pub fn spawn_heartbeat(
    workspace: Arc<Workspace>,
    llm: Arc<dyn LlmProvider>,
    response_tx: Option<mpsc::Sender<OutgoingResponse>>,
-    store: Option<Arc<dyn Database>>,
+    store: Option<AdminScope>,
 ) -> tokio::task::JoinHandle<()> {
    let mut runner = HeartbeatRunner::new(config, hygiene_config, workspace, llm);
    if let Some(tx) = response_tx {
@@ -512,8 +512,8 @@ pub fn spawn_heartbeat(
    })
 }

-/// Spawn a multi-user heartbeat runner that cycles through all users that
-/// own routines (enabled or not). Each tick, it queries the DB for distinct
+/// Spawn a multi-user heartbeat runner that cycles through all users who
+/// have routines (enabled or not). Each tick, it queries the DB for distinct
 /// user_ids, creates a per-user workspace, and runs a heartbeat check for
 /// each user concurrently. Per-user failure counts are tracked independently.
 pub fn spawn_multi_user_heartbeat(
@@ -521,7 +521,7 @@ pub fn spawn_multi_user_heartbeat(
    hygiene_config: HygieneConfig,
    llm: Arc<dyn LlmProvider>,
    response_tx: Option<mpsc::Sender<OutgoingResponse>>,
-    store: Arc<dyn Database>,
+    store: AdminScope,
 ) -> tokio::task::JoinHandle<()> {
    tokio::spawn(async move {
        if !config.enabled {
@@ -574,8 +574,11 @@ pub fn spawn_multi_user_heartbeat(
                }
            };

-            // Run all user heartbeats concurrently so one slow LLM call
-            // doesn't block others.
+            // Run user heartbeats (and hygiene) concurrently so one slow LLM
+            // call doesn't block others. Cap concurrency to avoid flooding the
+            // LLM provider. Hygiene runs inside the same JoinSet so it is
+            // tracked and bounded by the same concurrency cap.
+            const MAX_CONCURRENT_HEARTBEATS: usize = 8;
            let mut join_set = tokio::task::JoinSet::new();

            for user_id in &user_ids {
@@ -585,38 +588,45 @@ pub fn spawn_multi_user_heartbeat(
                    continue;
                }

-                let workspace = Arc::new(Workspace::new_with_db(user_id, store.clone()));
+                let workspace = Arc::new(Workspace::new_with_db(user_id, Arc::clone(store.db())));

-                // Run memory hygiene per user (same as single-user heartbeat).
-                let hygiene_ws = Arc::clone(&workspace);
-                let hygiene_cfg = hygiene_config.clone();
-                let hygiene_user = user_id.clone();
-                tokio::spawn(async move {
-                    let report =
-                        crate::workspace::hygiene::run_if_due(&hygiene_ws, &hygiene_cfg).await;
+                // Drain completed tasks to stay within the concurrency cap.
+                while join_set.len() >= MAX_CONCURRENT_HEARTBEATS {
+                    if let Some(join_result) = join_set.join_next().await {
+                        collect_heartbeat_result(join_result, &mut user_failures, &config);
+                    }
+                }
+
+                let uid = user_id.clone();
+                // In multi-tenant mode, clear notify_user_id so that
+                // HeartbeatRunner::send_notification falls back to
+                // workspace.user_id() — each user's heartbeat should persist
+                // and notify that user, not the shared config target.
+                let mut cfg = config.clone();
+                cfg.notify_user_id = None;
+                let hyg = hygiene_config.clone();
+                let llm_clone = llm.clone();
+                let tx = response_tx.clone();
+                let admin = store.clone();
+
+                join_set.spawn(async move {
+                    // Run memory hygiene per user (same as single-user heartbeat)
+                    // inside the tracked task so concurrency is bounded.
+                    let report = crate::workspace::hygiene::run_if_due(&workspace, &hyg).await;
                    if report.had_work() {
                        tracing::info!(
-                            user_id = hygiene_user,
+                            user_id = uid,
                            daily_logs_deleted = report.daily_logs_deleted,
                            conversation_docs_deleted = report.conversation_docs_deleted,
                            "multi-user heartbeat: memory hygiene deleted stale documents"
                        );
                    }
-                });

-                let uid = user_id.clone();
-                let cfg = config.clone();
-                let hyg = hygiene_config.clone();
-                let llm_clone = llm.clone();
-                let tx = response_tx.clone();
-                let st = store.clone();
-
-                join_set.spawn(async move {
                    let mut runner = HeartbeatRunner::new(cfg, hyg, workspace, llm_clone);
                    if let Some(tx) = tx {
                        runner = runner.with_response_channel(tx);
                    }
-                    runner = runner.with_store(st);
+                    runner = runner.with_store(admin);

                    let result = runner.check_heartbeat().await;
                    if let HeartbeatResult::NeedsAttention(msg) = &result {
@@ -626,41 +636,57 @@ pub fn spawn_multi_user_heartbeat(
                });
            }

-            // Collect results and update failure counts
-            while let Some(Ok((uid, result))) = join_set.join_next().await {
-                match result {
-                    HeartbeatResult::Ok => {
-                        tracing::trace!(user_id = uid, "Multi-user heartbeat OK");
-                        user_failures.remove(&uid);
-                    }
-                    HeartbeatResult::NeedsAttention(_) => {
-                        tracing::info!(user_id = uid, "Multi-user heartbeat needs attention");
-                        user_failures.remove(&uid);
-                    }
-                    HeartbeatResult::Skipped => {}
-                    HeartbeatResult::Failed(err) => {
-                        let count = user_failures.entry(uid.clone()).or_insert(0);
-                        *count += 1;
-                        tracing::error!(
-                            user_id = uid,
-                            consecutive_failures = *count,
-                            "Multi-user heartbeat failed: {}",
-                            err
-                        );
-                        if *count >= config.max_failures {
-                            tracing::error!(
-                                user_id = uid,
-                                "Multi-user heartbeat disabled for user after {} consecutive failures",
-                                count
-                            );
-                        }
-                    }
-                }
+            // Collect remaining results and update failure counts
+            while let Some(join_result) = join_set.join_next().await {
+                collect_heartbeat_result(join_result, &mut user_failures, &config);
            }
        }
    })
 }

+/// Process a single JoinSet result from the multi-user heartbeat loop.
+fn collect_heartbeat_result(
+    join_result: Result<(String, HeartbeatResult), tokio::task::JoinError>,
+    user_failures: &mut std::collections::HashMap<String, u32>,
+    config: &HeartbeatConfig,
+) {
+    let (uid, result) = match join_result {
+        Ok(pair) => pair,
+        Err(e) => {
+            tracing::error!("Multi-user heartbeat task panicked: {}", e);
+            return;
+        }
+    };
+    match result {
+        HeartbeatResult::Ok => {
+            tracing::trace!(user_id = uid, "Multi-user heartbeat OK");
+            user_failures.remove(&uid);
+        }
+        HeartbeatResult::NeedsAttention(_) => {
+            tracing::info!(user_id = uid, "Multi-user heartbeat needs attention");
+            user_failures.remove(&uid);
+        }
+        HeartbeatResult::Skipped => {}
+        HeartbeatResult::Failed(err) => {
+            let count = user_failures.entry(uid.clone()).or_insert(0);
+            *count += 1;
+            tracing::error!(
+                user_id = uid,
+                consecutive_failures = *count,
+                "Multi-user heartbeat failed: {}",
+                err
+            );
+            if *count >= config.max_failures {
+                tracing::error!(
+                    user_id = uid,
+                    "Multi-user heartbeat disabled for user after {} consecutive failures",
+                    count
+                );
+            }
+        }
+    }
+}
+
 #[cfg(test)]
 mod tests {
    use super::*;
@@ -879,7 +905,7 @@ mod tests {
            Arc<crate::workspace::Workspace>,
            Arc<dyn crate::llm::LlmProvider>,
            Option<tokio::sync::mpsc::Sender<crate::channels::OutgoingResponse>>,
-            Option<Arc<dyn crate::db::Database>>,
+            Option<AdminScope>,
        ) -> tokio::task::JoinHandle<()> = spawn_heartbeat;
        let _ = _fn_ptr;
    }
@@ -21,8 +21,8 @@ use tokio::task::JoinHandle;
 use uuid::Uuid;

 use crate::channels::IncomingMessage;
-use crate::channels::web::types::SseEvent;
 use crate::context::{ContextManager, JobState};
+use ironclaw_common::AppEvent;

 /// Route context for forwarding job monitor events back to the user's channel.
 #[derive(Debug, Clone)]
@@ -36,15 +36,15 @@ pub struct JobMonitorRoute {
 /// injects assistant messages into the agent loop.
 ///
 /// The monitor forwards:
-/// - `SseEvent::JobMessage` (assistant role): injected as incoming messages so
+/// - `AppEvent::JobMessage` (assistant role): injected as incoming messages so
 ///   the main agent can read and relay to the user.
-/// - `SseEvent::JobResult`: injected as a completion notice, then the task exits.
+/// - `AppEvent::JobResult`: injected as a completion notice, then the task exits.
 ///
 /// Tool use/result and status events are intentionally skipped (too noisy for
 /// the main agent's context window).
 pub fn spawn_job_monitor(
    job_id: Uuid,
-    event_rx: broadcast::Receiver<(Uuid, String, SseEvent)>,
+    event_rx: broadcast::Receiver<(Uuid, String, AppEvent)>,
    inject_tx: mpsc::Sender<IncomingMessage>,
    route: JobMonitorRoute,
 ) -> JoinHandle<()> {
@@ -56,7 +56,7 @@ pub fn spawn_job_monitor(
 /// jobs don't stay `InProgress` forever in the `ContextManager`.
 pub fn spawn_job_monitor_with_context(
    job_id: Uuid,
-    mut event_rx: broadcast::Receiver<(Uuid, String, SseEvent)>,
+    mut event_rx: broadcast::Receiver<(Uuid, String, AppEvent)>,
    inject_tx: mpsc::Sender<IncomingMessage>,
    route: JobMonitorRoute,
    context_manager: Option<Arc<ContextManager>>,
@@ -74,7 +74,7 @@ pub fn spawn_job_monitor_with_context(
                    }

                    match event {
-                        SseEvent::JobMessage { role, content, .. } if role == "assistant" => {
+                        AppEvent::JobMessage { role, content, .. } if role == "assistant" => {
                            let mut msg = IncomingMessage::new(
                                route.channel.clone(),
                                route.user_id.clone(),
@@ -92,7 +92,7 @@ pub fn spawn_job_monitor_with_context(
                                break;
                            }
                        }
-                        SseEvent::JobResult { status, .. } => {
+                        AppEvent::JobResult { status, .. } => {
                            // Transition in-memory state so the job frees its
                            // max_jobs slot and query tools show the final state.
                            if let Some(ref cm) = context_manager {
@@ -162,7 +162,7 @@ pub fn spawn_job_monitor_with_context(
 /// inject messages into) but we still need to free the `max_jobs` slot.
 pub fn spawn_completion_watcher(
    job_id: Uuid,
-    mut event_rx: broadcast::Receiver<(Uuid, String, SseEvent)>,
+    mut event_rx: broadcast::Receiver<(Uuid, String, AppEvent)>,
    context_manager: Arc<ContextManager>,
 ) -> JoinHandle<()> {
    let short_id = job_id.to_string()[..8].to_string();
@@ -170,7 +170,7 @@ pub fn spawn_completion_watcher(
    tokio::spawn(async move {
        loop {
            match event_rx.recv().await {
-                Ok((ev_job_id, _user_id, SseEvent::JobResult { status, .. }))
+                Ok((ev_job_id, _user_id, AppEvent::JobResult { status, .. }))
                    if ev_job_id == job_id =>
                {
                    let target = if status == "completed" {
@@ -229,7 +229,7 @@ mod tests {

    #[tokio::test]
    async fn test_monitor_forwards_assistant_messages() {
-        let (event_tx, _) = broadcast::channel::<(Uuid, String, SseEvent)>(16);
+        let (event_tx, _) = broadcast::channel::<(Uuid, String, AppEvent)>(16);
        let (inject_tx, mut inject_rx) = mpsc::channel::<IncomingMessage>(16);

        let job_id = Uuid::new_v4();
@@ -240,7 +240,7 @@ mod tests {
            .send((
                job_id,
                "test-user".to_string(),
-                SseEvent::JobMessage {
+                AppEvent::JobMessage {
                    job_id: job_id.to_string(),
                    role: "assistant".to_string(),
                    content: "I found a bug".to_string(),
@@ -262,7 +262,7 @@ mod tests {

    #[tokio::test]
    async fn test_monitor_ignores_other_jobs() {
-        let (event_tx, _) = broadcast::channel::<(Uuid, String, SseEvent)>(16);
+        let (event_tx, _) = broadcast::channel::<(Uuid, String, AppEvent)>(16);
        let (inject_tx, mut inject_rx) = mpsc::channel::<IncomingMessage>(16);

        let job_id = Uuid::new_v4();
@@ -274,7 +274,7 @@ mod tests {
            .send((
                other_job_id,
                "test-user".to_string(),
-                SseEvent::JobMessage {
+                AppEvent::JobMessage {
                    job_id: other_job_id.to_string(),
                    role: "assistant".to_string(),
                    content: "wrong job".to_string(),
@@ -293,7 +293,7 @@ mod tests {

    #[tokio::test]
    async fn test_monitor_exits_on_job_result() {
-        let (event_tx, _) = broadcast::channel::<(Uuid, String, SseEvent)>(16);
+        let (event_tx, _) = broadcast::channel::<(Uuid, String, AppEvent)>(16);
        let (inject_tx, mut inject_rx) = mpsc::channel::<IncomingMessage>(16);

        let job_id = Uuid::new_v4();
@@ -304,7 +304,7 @@ mod tests {
            .send((
                job_id,
                "test-user".to_string(),
-                SseEvent::JobResult {
+                AppEvent::JobResult {
                    job_id: job_id.to_string(),
                    status: "completed".to_string(),
                    session_id: None,
@@ -329,7 +329,7 @@ mod tests {

    #[tokio::test]
    async fn test_monitor_skips_tool_events() {
-        let (event_tx, _) = broadcast::channel::<(Uuid, String, SseEvent)>(16);
+        let (event_tx, _) = broadcast::channel::<(Uuid, String, AppEvent)>(16);
        let (inject_tx, mut inject_rx) = mpsc::channel::<IncomingMessage>(16);

        let job_id = Uuid::new_v4();
@@ -340,7 +340,7 @@ mod tests {
            .send((
                job_id,
                "test-user".to_string(),
-                SseEvent::JobToolUse {
+                AppEvent::JobToolUse {
                    job_id: job_id.to_string(),
                    tool_name: "shell".to_string(),
                    input: serde_json::json!({"command": "ls"}),
@@ -353,7 +353,7 @@ mod tests {
            .send((
                job_id,
                "test-user".to_string(),
-                SseEvent::JobMessage {
+                AppEvent::JobMessage {
                    job_id: job_id.to_string(),
                    role: "user".to_string(),
                    content: "user prompt".to_string(),
@@ -409,7 +409,7 @@ mod tests {
            .await
            .unwrap();

-        let (event_tx, _) = broadcast::channel::<(Uuid, String, SseEvent)>(16);
+        let (event_tx, _) = broadcast::channel::<(Uuid, String, AppEvent)>(16);
        let (inject_tx, mut inject_rx) = mpsc::channel::<IncomingMessage>(16);

        let handle = spawn_job_monitor_with_context(
@@ -425,7 +425,7 @@ mod tests {
            .send((
                job_id,
                "test-user".to_string(),
-                SseEvent::JobResult {
+                AppEvent::JobResult {
                    job_id: job_id.to_string(),
                    status: "completed".to_string(),
                    session_id: None,
@@ -458,7 +458,7 @@ mod tests {
            .await
            .unwrap();

-        let (event_tx, _) = broadcast::channel::<(Uuid, String, SseEvent)>(16);
+        let (event_tx, _) = broadcast::channel::<(Uuid, String, AppEvent)>(16);
        let (inject_tx, mut inject_rx) = mpsc::channel::<IncomingMessage>(16);

        let handle = spawn_job_monitor_with_context(
@@ -474,7 +474,7 @@ mod tests {
            .send((
                job_id,
                "test-user".to_string(),
-                SseEvent::JobResult {
+                AppEvent::JobResult {
                    job_id: job_id.to_string(),
                    status: "failed".to_string(),
                    session_id: None,
@@ -507,14 +507,14 @@ mod tests {
            .await
            .unwrap();

-        let (event_tx, _) = broadcast::channel::<(Uuid, String, SseEvent)>(16);
+        let (event_tx, _) = broadcast::channel::<(Uuid, String, AppEvent)>(16);
        let handle = spawn_completion_watcher(job_id, event_tx.subscribe(), Arc::clone(&cm));

        event_tx
            .send((
                job_id,
                "test-user".to_string(),
-                SseEvent::JobResult {
+                AppEvent::JobResult {
                    job_id: job_id.to_string(),
                    status: "completed".to_string(),
                    session_id: None,
@@ -18,21 +18,22 @@ use std::time::Duration;
 use chrono::Utc;
 use regex::Regex;
 use tokio::sync::{RwLock, mpsc};
+use tokio::task::JoinHandle;
 use uuid::Uuid;

 use crate::agent::Scheduler;
 use crate::agent::routine::{
    NotifyConfig, Routine, RoutineAction, RoutineRun, RunStatus, Trigger, next_cron_fire,
 };
-use crate::channels::OutgoingResponse;
+use crate::channels::{IncomingMessage, OutgoingResponse};
 use crate::config::RoutineConfig;
 use crate::context::{JobContext, JobState};
-use crate::db::Database;
 use crate::error::RoutineError;
 use crate::extensions::ExtensionManager;
 use crate::llm::{
    ChatMessage, CompletionRequest, FinishReason, LlmProvider, ToolCall, ToolCompletionRequest,
 };
+use crate::tenant::AdminScope;
 use crate::tools::{
    ToolError, ToolRegistry, autonomous_allowed_tool_names, autonomous_unavailable_message,
    prepare_tool_params,
@@ -45,6 +46,11 @@ enum EventMatcher {
    System { routine: Routine },
 }

+struct TriggeredRoutine {
+    routine: Routine,
+    detail: String,
+}
+
 /// Distinguishes why sandbox is unavailable so error messages are accurate.
 #[derive(Debug, Clone, Copy, PartialEq, Eq)]
 pub enum SandboxReadiness {
@@ -56,10 +62,44 @@ pub enum SandboxReadiness {
    DockerUnavailable,
 }

+/// Check whether an event-triggered routine's user/channel filters match an
+/// incoming message.
+///
+/// Returns `true` if:
+/// - The routine has an `Event` trigger (non-Event routines always return `false`)
+/// - The routine's `user_id` matches the message's user scope
+/// - The routine's channel filter (if any) matches the message channel
+///   case-insensitively
+///
+/// This is a pure function extracted from `check_event_triggers` so the
+/// filter logic can be unit-tested without async infrastructure.
+pub(crate) fn routine_matches_message(routine: &Routine, message: &IncomingMessage) -> bool {
+    // Only Event-triggered routines can match incoming messages.
+    if !matches!(routine.trigger, Trigger::Event { .. }) {
+        return false;
+    }
+
+    // User ownership filter — only fire routines scoped to this user.
+    if routine.user_id != message.user_id {
+        return false;
+    }
+
+    // Channel filter (case-insensitive, matching emit_system_event behavior)
+    if let Trigger::Event {
+        channel: Some(ch), ..
+    } = &routine.trigger
+        && !ch.eq_ignore_ascii_case(&message.channel)
+    {
+        return false;
+    }
+
+    true
+}
+
 /// The routine execution engine.
 pub struct RoutineEngine {
    config: RoutineConfig,
-    store: Arc<dyn Database>,
+    store: AdminScope,
    llm: Arc<dyn LlmProvider>,
    workspace: Arc<Workspace>,
    /// Sender for notifications (routed to channel manager).
@@ -88,7 +128,7 @@ impl RoutineEngine {
    #[allow(clippy::too_many_arguments)]
    pub fn new(
        config: RoutineConfig,
-        store: Arc<dyn Database>,
+        store: AdminScope,
        llm: Arc<dyn LlmProvider>,
        workspace: Arc<Workspace>,
        notify_tx: mpsc::Sender<OutgoingResponse>,
@@ -167,10 +207,45 @@ impl RoutineEngine {
    }

    /// Check incoming message against event triggers. Returns number of routines fired.
+    pub async fn check_event_triggers(&self, message: &IncomingMessage, content: &str) -> usize {
+        let triggered = self.matching_event_triggers(message, content).await;
+        let fired = triggered.len();
+        for triggered in triggered {
+            std::mem::drop(self.spawn_fire(triggered.routine, "event", Some(triggered.detail)));
+        }
+        fired
+    }
+
+    /// Fire matching event-triggered routines and wait for them to complete.
    ///
-    /// 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 {
+    /// Used by single-message REPL mode so the process does not exit before
+    /// background event-triggered routines finish.
+    pub async fn check_event_triggers_and_wait(
+        &self,
+        message: &IncomingMessage,
+        content: &str,
+    ) -> usize {
+        let triggered = self.matching_event_triggers(message, content).await;
+        let fired = triggered.len();
+        let handles: Vec<JoinHandle<()>> = triggered
+            .into_iter()
+            .map(|triggered| self.spawn_fire(triggered.routine, "event", Some(triggered.detail)))
+            .collect();
+
+        for handle in handles {
+            if let Err(e) = handle.await {
+                tracing::warn!(error = %e, "Event-triggered routine task failed");
+            }
+        }
+
+        fired
+    }
+
+    async fn matching_event_triggers(
+        &self,
+        message: &IncomingMessage,
+        content: &str,
+    ) -> Vec<TriggeredRoutine> {
        let cache = self.event_cache.read().await;

        // Early return if there are no message matchers at all.
@@ -178,10 +253,9 @@ impl RoutineEngine {
            .iter()
            .any(|m| matches!(m, EventMatcher::Message { .. }))
        {
-            return 0;
+            return Vec::new();
        }
-
-        let mut fired = 0;
+        let mut triggered = Vec::new();

        // Collect routine IDs for batch query
        let routine_ids: Vec<Uuid> = cache
@@ -193,13 +267,13 @@ impl RoutineEngine {
            .collect();

        if routine_ids.is_empty() {
-            return 0;
+            return Vec::new();
        }

        // Single batch query instead of N queries
        let concurrent_counts = match self.batch_concurrent_counts(&routine_ids).await {
            Some(counts) => counts,
-            None => return 0,
+            None => return Vec::new(),
        };

        for matcher in cache.iter() {
@@ -208,16 +282,24 @@ impl RoutineEngine {
                EventMatcher::System { .. } => continue,
            };

-            if routine.user_id != user_id {
-                continue;
-            }
-
-            // Channel filter
-            if let Trigger::Event {
-                channel: Some(ch), ..
-            } = &routine.trigger
-                && ch != channel
-            {
+            // User ownership + channel filter (extracted for testability).
+            if !routine_matches_message(routine, message) {
+                // User mismatch is expected for multi-user setups — keep at
+                // trace to avoid one log per routine per inbound message.
+                if routine.user_id != message.user_id {
+                    tracing::trace!(
+                        routine = %routine.name,
+                        routine_user = %routine.user_id,
+                        message_user = %message.user_id,
+                        "Skipped: user scope mismatch"
+                    );
+                } else {
+                    tracing::debug!(
+                        routine = %routine.name,
+                        channel = %message.channel,
+                        "Skipped: channel mismatch"
+                    );
+                }
                continue;
            }

@@ -228,14 +310,14 @@ impl RoutineEngine {

            // Cooldown check
            if !self.check_cooldown(routine) {
-                tracing::trace!(routine = %routine.name, "Skipped: cooldown active");
+                tracing::debug!(routine = %routine.name, "Skipped: cooldown active");
                continue;
            }

            // Concurrent run check (using batch-loaded counts)
            let running_count = concurrent_counts.get(&routine.id).copied().unwrap_or(0);
            if running_count >= routine.guardrails.max_concurrent as i64 {
-                tracing::trace!(routine = %routine.name, "Skipped: max concurrent reached");
+                tracing::debug!(routine = %routine.name, "Skipped: max concurrent reached");
                continue;
            }

@@ -246,11 +328,13 @@ impl RoutineEngine {
            }

            let detail = truncate(content, 200);
-            self.spawn_fire(routine.clone(), "event", Some(detail));
-            fired += 1;
+            triggered.push(TriggeredRoutine {
+                routine: routine.clone(),
+                detail,
+            });
        }

-        fired
+        triggered
    }

    /// Emit a structured event to system-event routines.
@@ -698,12 +782,22 @@ impl RoutineEngine {
            });
        }

+        // Per-user workspace (same pattern as spawn_fire).
+        let routine_workspace = if routine.user_id == self.workspace.user_id() {
+            self.workspace.clone()
+        } else {
+            Arc::new(Workspace::new_with_db(
+                &routine.user_id,
+                Arc::clone(self.store.db()),
+            ))
+        };
+
        // Execute inline for manual triggers (caller wants to wait)
        let engine = EngineContext {
            config: self.config.clone(),
            store: self.store.clone(),
            llm: self.llm.clone(),
-            workspace: self.workspace.clone(),
+            workspace: routine_workspace,
            notify_tx: self.notify_tx.clone(),
            running_count: self.running_count.clone(),
            scheduler: self.scheduler.clone(),
@@ -806,7 +900,12 @@ impl RoutineEngine {
    }

    /// Spawn a fire in a background task.
-    fn spawn_fire(&self, routine: Routine, trigger_type: &str, trigger_detail: Option<String>) {
+    fn spawn_fire(
+        &self,
+        routine: Routine,
+        trigger_type: &str,
+        trigger_detail: Option<String>,
+    ) -> JoinHandle<()> {
        let run = RoutineRun {
            id: Uuid::new_v4(),
            routine_id: routine.id,
@@ -827,7 +926,10 @@ impl RoutineEngine {
        let routine_workspace = if routine.user_id == self.workspace.user_id() {
            self.workspace.clone()
        } else {
-            Arc::new(Workspace::new_with_db(&routine.user_id, self.store.clone()))
+            Arc::new(Workspace::new_with_db(
+                &routine.user_id,
+                Arc::clone(self.store.db()),
+            ))
        };

        let engine = EngineContext {
@@ -852,7 +954,7 @@ impl RoutineEngine {
                return;
            }
            execute_routine(engine, routine, run).await;
-        });
+        })
    }

    fn check_cooldown(&self, routine: &Routine) -> bool {
@@ -887,7 +989,7 @@ impl RoutineEngine {
 /// an active state (Pending/InProgress/Stuck). Maps the final `JobState` to
 /// a `RunStatus` for the routine run.
 struct FullJobWatcher {
-    store: Arc<dyn Database>,
+    store: AdminScope,
    job_id: Uuid,
    routine_name: String,
 }
@@ -898,7 +1000,7 @@ impl FullJobWatcher {
    /// 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 {
+    fn new(store: AdminScope, job_id: Uuid, routine_name: String) -> Self {
        Self {
            store,
            job_id,
@@ -970,7 +1072,7 @@ impl FullJobWatcher {
 /// Shared context passed to the execution function.
 struct EngineContext {
    config: RoutineConfig,
-    store: Arc<dyn Database>,
+    store: AdminScope,
    llm: Arc<dyn LlmProvider>,
    workspace: Arc<Workspace>,
    notify_tx: mpsc::Sender<OutgoingResponse>,
@@ -987,48 +1089,134 @@ async fn execute_routine(ctx: EngineContext, routine: Routine, run: RoutineRun)
    // Increment running count (atomic: survives panics in the execution below)
    ctx.running_count.fetch_add(1, Ordering::Relaxed);

-    let result = match &routine.action {
-        RoutineAction::Lightweight {
-            prompt,
-            context_paths,
-            max_tokens,
-            use_tools,
-            max_tool_rounds,
-        } => {
-            execute_lightweight(
-                &ctx,
-                &routine,
-                prompt,
-                context_paths,
-                *max_tokens,
-                *use_tools,
-                *max_tool_rounds,
-            )
-            .await
+    // Retry constants for transient lightweight execution failures.
+    const MAX_RETRIES: u32 = 3;
+    const BASE_DELAY_MS: u64 = 1000;
+
+    let is_lightweight = matches!(routine.action, RoutineAction::Lightweight { .. });
+
+    // The retry block returns both the execution result and any accumulated
+    // token count so that usage is preserved even on final failure.
+    let (result, accumulated_tokens) = {
+        let mut attempt = 0u32;
+        // Track accumulated tokens as Option to preserve None semantics:
+        // None = no attempt reported tokens; Some(n) = at least one attempt did.
+        let mut accumulated_tokens: Option<i32> = None;
+        let uses_tools = matches!(
+            routine.action,
+            RoutineAction::Lightweight {
+                use_tools: true,
+                ..
+            }
+        ) && ctx.config.lightweight_tools_enabled;
+
+        /// Extract partial_tokens from any RoutineError variant that carries them.
+        fn extract_partial_tokens(e: &RoutineError) -> Option<i32> {
+            match e {
+                RoutineError::LlmFailed {
+                    partial_tokens: Some(t),
+                    ..
+                }
+                | RoutineError::EmptyResponse {
+                    partial_tokens: Some(t),
+                }
+                | RoutineError::TruncatedResponse {
+                    partial_tokens: Some(t),
+                } => Some(*t),
+                _ => None,
+            }
        }
-        RoutineAction::FullJob {
-            title,
-            description,
-            max_iterations,
-        } => {
-            let execution = FullJobExecutionConfig {
-                title,
-                description,
-                max_iterations: *max_iterations,
+
+        /// Merge an optional partial token count into the accumulator,
+        /// only materializing Some when at least one source had Some.
+        fn accumulate(acc: Option<i32>, partial: Option<i32>) -> Option<i32> {
+            match (acc, partial) {
+                (Some(a), Some(p)) => Some(a.saturating_add(p)),
+                (Some(a), None) => Some(a),
+                (None, p) => p,
+            }
+        }
+
+        loop {
+            let execution_result = match &routine.action {
+                RoutineAction::Lightweight {
+                    prompt,
+                    context_paths,
+                    max_tokens,
+                    use_tools,
+                    max_tool_rounds,
+                } => {
+                    execute_lightweight(
+                        &ctx,
+                        &routine,
+                        prompt,
+                        context_paths,
+                        *max_tokens,
+                        *use_tools,
+                        *max_tool_rounds,
+                    )
+                    .await
+                }
+                RoutineAction::FullJob {
+                    title,
+                    description,
+                    max_iterations,
+                } => {
+                    let execution = FullJobExecutionConfig {
+                        title,
+                        description,
+                        max_iterations: *max_iterations,
+                    };
+                    execute_full_job(&ctx, &routine, &run, &execution).await
+                }
            };
-            execute_full_job(&ctx, &routine, &run, &execution).await
+
+            match execution_result {
+                Ok((status, summary, tokens)) => {
+                    // Merge tokens: only produce Some when at least one source had Some.
+                    let total = accumulate(accumulated_tokens, tokens);
+                    break (Ok((status, summary, total)), accumulated_tokens);
+                }
+                Err(ref e)
+                    if is_lightweight
+                        && !uses_tools
+                        && e.is_retryable()
+                        // Skip outer retry for LlmFailed — RetryProvider already
+                        // retries transient LLM errors with its own budget. Retrying
+                        // here would create a multiplicative retry count.
+                        && !matches!(e, RoutineError::LlmFailed { .. })
+                        && attempt < MAX_RETRIES =>
+                {
+                    // Accumulate partial tokens from the failed attempt.
+                    accumulated_tokens = accumulate(accumulated_tokens, extract_partial_tokens(e));
+
+                    attempt += 1;
+
+                    let delay = Duration::from_millis(
+                        BASE_DELAY_MS.saturating_mul(2u64.saturating_pow(attempt - 1)),
+                    );
+                    tracing::event!(target: "transient_routine_errors", tracing::Level::WARN, routine = %routine.name, attempt = attempt, max_retries = MAX_RETRIES, delay_ms = delay.as_millis() as u64, "Transient routine error, retrying: {}", e);
+                    tokio::time::sleep(delay).await;
+                }
+                Err(e) => {
+                    // Accumulate tokens from the final failed attempt.
+                    accumulated_tokens = accumulate(accumulated_tokens, extract_partial_tokens(&e));
+                    break (Err(e), accumulated_tokens);
+                }
+            }
        }
    };

    // Decrement running count
    ctx.running_count.fetch_sub(1, Ordering::Relaxed);

-    // Process result
+    // Process result — on failure, preserve accumulated token total from
+    // earlier retry attempts so usage reporting stays accurate.
    let (status, summary, tokens) = match result {
        Ok(execution) => execution,
        Err(e) => {
            tracing::error!(routine = %routine.name, "Execution failed: {}", e);
-            (RunStatus::Failed, Some(e.to_string()), None)
+            (RunStatus::Failed, Some(e.to_string()), accumulated_tokens)
        }
    };

@@ -1409,13 +1597,14 @@ async fn execute_lightweight_no_tools(
        .with_max_tokens(effective_max_tokens)
        .with_temperature(0.3);

-    let response = ctx
-        .llm
-        .complete(request)
-        .await
-        .map_err(|e| RoutineError::LlmFailed {
+    let response = ctx.llm.complete(request).await.map_err(|e| {
+        let retryable = crate::llm::retry::is_retryable(&e);
+        RoutineError::LlmFailed {
            reason: e.to_string(),
-        })?;
+            partial_tokens: None,
+            retryable,
+        }
+    })?;

    handle_text_response(
        &response.content,
@@ -1436,12 +1625,18 @@ fn handle_text_response(
 ) -> Result<(RunStatus, Option<String>, Option<i32>), RoutineError> {
    let content = content.trim();

-    // Empty content guard
+    // Empty content guard — carry consumed tokens so the retry loop can
+    // accumulate them even when the response shape is invalid.
    if content.is_empty() {
+        let consumed = Some((total_input_tokens + total_output_tokens) as i32);
        return if finish_reason == FinishReason::Length {
-            Err(RoutineError::TruncatedResponse)
+            Err(RoutineError::TruncatedResponse {
+                partial_tokens: consumed,
+            })
        } else {
-            Err(RoutineError::EmptyResponse)
+            Err(RoutineError::EmptyResponse {
+                partial_tokens: consumed,
+            })
        };
    }

@@ -1511,18 +1706,23 @@ async fn execute_lightweight_with_tools(
        let force_text = iteration >= max_iterations;

        if force_text {
-            // Final iteration: no tools, just get text response
+            // Final iteration: no tools, just get text response.
+            // Claude 4.6 rejects assistant prefill; NEAR AI rejects any non-user-ending
+            // conversation. Ensure the last message is user-role.
+            crate::util::ensure_ends_with_user_message(&mut messages);
            let request = CompletionRequest::new(messages)
                .with_max_tokens(effective_max_tokens)
                .with_temperature(0.3);

-            let response =
-                ctx.llm
-                    .complete(request)
-                    .await
-                    .map_err(|e| RoutineError::LlmFailed {
-                        reason: e.to_string(),
-                    })?;
+            let response = ctx.llm.complete(request).await.map_err(|e| {
+                let partial = (total_input_tokens + total_output_tokens) as i32;
+                let retryable = crate::llm::retry::is_retryable(&e);
+                RoutineError::LlmFailed {
+                    reason: e.to_string(),
+                    partial_tokens: if partial > 0 { Some(partial) } else { None },
+                    retryable,
+                }
+            })?;

            total_input_tokens += response.input_tokens;
            total_output_tokens += response.output_tokens;
@@ -1549,8 +1749,12 @@ async fn execute_lightweight_with_tools(
                .with_temperature(0.3);

            let response = ctx.llm.complete_with_tools(request).await.map_err(|e| {
+                let partial = (total_input_tokens + total_output_tokens) as i32;
+                let retryable = crate::llm::retry::is_retryable(&e);
                RoutineError::LlmFailed {
                    reason: e.to_string(),
+                    partial_tokens: if partial > 0 { Some(partial) } else { None },
+                    retryable,
                }
            })?;

@@ -1723,6 +1927,7 @@ async fn execute_routine_tool(
 }

 /// Send a notification based on the routine's notify config and run status.
+#[allow(clippy::too_many_arguments)]
 async fn send_notification(
    tx: &mpsc::Sender<OutgoingResponse>,
    notify: &NotifyConfig,
@@ -1790,6 +1995,13 @@ pub fn spawn_cron_ticker(
        engine.check_cron_triggers().await;

        let mut ticker = tokio::time::interval(interval);
+        ticker.set_missed_tick_behavior(tokio::time::MissedTickBehavior::Skip);
+        // Periodic event cache refresh so web/CLI mutations are picked up
+        // without requiring tool-path code to call refresh_event_cache().
+        // Uses wall-clock elapsed time so the refresh cadence is stable
+        // regardless of the cron tick interval configuration.
+        let refresh_interval = Duration::from_secs(60);
+        let mut last_refresh = tokio::time::Instant::now();

        loop {
            ticker.tick().await;
@@ -1797,7 +2009,11 @@ pub fn spawn_cron_ticker(
            // never races with FullJobWatcher instances from this process.
            engine.sync_dispatched_runs().await;
            engine.check_cron_triggers().await;
-            engine.sync_dispatched_runs().await;
+
+            if last_refresh.elapsed() >= refresh_interval {
+                engine.refresh_event_cache().await;
+                last_refresh = tokio::time::Instant::now();
+            }
        }
    })
 }
@@ -1863,7 +2079,13 @@ fn strip_html_tags(s: &str) -> String {

 #[cfg(test)]
 mod tests {
-    use crate::agent::routine::{NotifyConfig, RunStatus};
+    use chrono::Utc;
+    use uuid::Uuid;
+
+    use crate::agent::routine::{
+        NotifyConfig, Routine, RoutineAction, RoutineGuardrails, RunStatus, Trigger,
+    };
+    use crate::channels::IncomingMessage;
    use crate::config::RoutineConfig;

    #[test]
@@ -2061,6 +2283,117 @@ mod tests {
        }
    }

+    /// Helper to build a test routine with the given user_id and trigger.
+    fn make_routine(user_id: &str, trigger: Trigger) -> Routine {
+        Routine {
+            id: Uuid::new_v4(),
+            name: "test".to_string(),
+            description: String::new(),
+            user_id: user_id.to_string(),
+            enabled: true,
+            trigger,
+            action: RoutineAction::Lightweight {
+                prompt: String::new(),
+                context_paths: vec![],
+                max_tokens: 1000,
+                use_tools: false,
+                max_tool_rounds: 0,
+            },
+            guardrails: RoutineGuardrails::default(),
+            notify: Default::default(),
+            last_run_at: None,
+            next_fire_at: None,
+            run_count: 0,
+            consecutive_failures: 0,
+            state: serde_json::Value::Null,
+            created_at: Utc::now(),
+            updated_at: Utc::now(),
+        }
+    }
+
+    /// Helper to build a test IncomingMessage.
+    fn make_message(user_id: &str, channel: &str, content: &str) -> IncomingMessage {
+        IncomingMessage {
+            id: Uuid::new_v4(),
+            channel: channel.to_string(),
+            user_id: user_id.to_string(),
+            owner_id: user_id.to_string(),
+            sender_id: user_id.to_string(),
+            user_name: None,
+            content: content.to_string(),
+            thread_id: None,
+            conversation_scope_id: None,
+            received_at: Utc::now(),
+            metadata: serde_json::Value::Null,
+            timezone: None,
+            attachments: vec![],
+            is_internal: false,
+        }
+    }
+
+    /// Regression test for issue #1051: event triggers used case-sensitive
+    /// channel comparison, so "Telegram" != "telegram" caused silent mismatch.
+    /// Tests the actual `routine_matches_message` function used in `check_event_triggers`.
+    #[test]
+    fn test_channel_filter_is_case_insensitive() {
+        let routine = make_routine(
+            "user1",
+            Trigger::Event {
+                pattern: ".*".to_string(),
+                channel: Some("Telegram".to_string()),
+            },
+        );
+        let msg = make_message("user1", "telegram", "hello");
+
+        // Case-insensitive channel match must succeed
+        assert!(super::routine_matches_message(&routine, &msg));
+
+        // Exact case must also work
+        let msg_exact = make_message("user1", "Telegram", "hello");
+        assert!(super::routine_matches_message(&routine, &msg_exact));
+
+        // Different channel must not match
+        let msg_wrong = make_message("user1", "discord", "hello");
+        assert!(!super::routine_matches_message(&routine, &msg_wrong));
+    }
+
+    /// Regression test for issue #1051: event triggers did not filter by
+    /// user_id, so routines from user A could fire on messages from user B.
+    /// Tests the actual `routine_matches_message` function used in `check_event_triggers`.
+    #[test]
+    fn test_event_trigger_requires_user_match() {
+        let routine = make_routine(
+            "alice",
+            Trigger::Event {
+                pattern: ".*".to_string(),
+                channel: None,
+            },
+        );
+
+        // Different user must not match
+        let msg_bob = make_message("bob", "telegram", "hello");
+        assert!(!super::routine_matches_message(&routine, &msg_bob));
+
+        // Same user must match
+        let msg_alice = make_message("alice", "telegram", "hello");
+        assert!(super::routine_matches_message(&routine, &msg_alice));
+    }
+
+    /// When no channel filter is set, any channel should match (given user matches).
+    #[test]
+    fn test_no_channel_filter_matches_any_channel() {
+        let routine = make_routine(
+            "user1",
+            Trigger::Event {
+                pattern: ".*".to_string(),
+                channel: None,
+            },
+        );
+
+        let msg = make_message("user1", "whatever_channel", "hello");
+        assert!(super::routine_matches_message(&routine, &msg));
+    }
+
    #[test]
    fn test_routine_tool_denylist_blocks_self_management_tools() {
        let denylisted = vec![
@@ -2280,6 +2613,104 @@ mod tests {
        }
    }

+    /// Regression test for #1320: transient errors are retried for lightweight
+    /// routines but not for full-job routines or hard failures.
+    #[test]
+    fn test_retry_classification_for_routine_errors() {
+        use crate::error::RoutineError;
+
+        // Transient errors (retryable for lightweight routines)
+        let transient_errors: Vec<RoutineError> = vec![
+            RoutineError::LlmFailed {
+                reason: "rate limit".into(),
+                partial_tokens: None,
+                retryable: true,
+            },
+            RoutineError::LlmFailed {
+                reason: "network timeout".into(),
+                partial_tokens: Some(42),
+                retryable: true,
+            },
+            RoutineError::EmptyResponse {
+                partial_tokens: None,
+            },
+            RoutineError::TruncatedResponse {
+                partial_tokens: Some(100),
+            },
+        ];
+        for err in &transient_errors {
+            assert!(err.is_retryable(), "{} should be retryable", err);
+        }
+
+        // Permanent LLM failures that should NOT be retried
+        // (retryable: false is set at conversion time by llm::retry::is_retryable)
+        let permanent_llm_errors: Vec<RoutineError> = vec![
+            RoutineError::LlmFailed {
+                reason: "Authentication failed for provider openai".into(),
+                partial_tokens: None,
+                retryable: false,
+            },
+            RoutineError::LlmFailed {
+                reason: "invalid_api_key: bad key".into(),
+                partial_tokens: None,
+                retryable: false,
+            },
+            RoutineError::LlmFailed {
+                reason: "content policy violation".into(),
+                partial_tokens: None,
+                retryable: false,
+            },
+            RoutineError::LlmFailed {
+                reason: "content_filter triggered".into(),
+                partial_tokens: None,
+                retryable: false,
+            },
+            RoutineError::LlmFailed {
+                reason: "context length exceeded: 150000 tokens used, 128000 allowed".into(),
+                partial_tokens: Some(100),
+                retryable: false,
+            },
+            RoutineError::LlmFailed {
+                reason: "model not available on provider anthropic".into(),
+                partial_tokens: None,
+                retryable: false,
+            },
+            RoutineError::LlmFailed {
+                reason: "content moderation flagged".into(),
+                partial_tokens: None,
+                retryable: false,
+            },
+        ];
+        for err in &permanent_llm_errors {
+            assert!(!err.is_retryable(), "{} should NOT be retryable", err);
+        }
+
+        // Hard failures (never retried)
+        let hard_errors: Vec<RoutineError> = vec![
+            RoutineError::Disabled {
+                name: "test".into(),
+            },
+            RoutineError::NotFound {
+                id: uuid::Uuid::new_v4(),
+            },
+            RoutineError::NotAuthorized {
+                id: uuid::Uuid::new_v4(),
+            },
+            RoutineError::MaxConcurrent {
+                name: "test".into(),
+            },
+            RoutineError::JobDispatchFailed {
+                reason: "no docker".into(),
+            },
+            RoutineError::Database {
+                reason: "connection refused".into(),
+            },
+        ];
+        for err in &hard_errors {
+            assert!(!err.is_retryable(), "{} should NOT be retryable", err);
+        }
+    }
+
    #[test]
    fn test_sanitize_summary_strips_control_chars() {
        use super::sanitize_summary;
@@ -11,12 +11,12 @@ use uuid::Uuid;
 use crate::agent::task::{Task, TaskContext, TaskOutput};
 use crate::config::AgentConfig;
 use crate::context::{ContextManager, JobContext, JobState};
-use crate::db::Database;
 use crate::error::{Error, JobError};
 use crate::extensions::ExtensionManager;
 use crate::hooks::HookRegistry;
 use crate::llm::LlmProvider;
 use crate::safety::SafetyLayer;
+use crate::tenant::AdminScope;
 use crate::tools::{
    ApprovalContext, ToolRegistry, autonomous_allowed_tool_names, autonomous_unavailable_error,
    prepare_tool_params,
@@ -52,7 +52,7 @@ struct ScheduledSubtask {
 pub struct SchedulerDeps {
    pub tools: Arc<ToolRegistry>,
    pub extension_manager: Option<Arc<ExtensionManager>>,
-    pub store: Option<Arc<dyn Database>>,
+    pub store: Option<AdminScope>,
    pub hooks: Arc<HookRegistry>,
 }

@@ -64,7 +64,7 @@ pub struct Scheduler {
    safety: Arc<SafetyLayer>,
    tools: Arc<ToolRegistry>,
    extension_manager: Option<Arc<ExtensionManager>>,
-    store: Option<Arc<dyn Database>>,
+    store: Option<AdminScope>,
    hooks: Arc<HookRegistry>,
    /// SSE manager for live job event streaming.
    sse_tx: Option<Arc<crate::channels::web::sse::SseManager>>,
@@ -267,6 +267,20 @@ impl Scheduler {
                });
            }

+            // Per-user concurrency check — only count jobs consuming a parallel
+            // execution slot (Pending/InProgress/Stuck), not Completed/Submitted.
+            if let Some(max_per_user) = self.config.max_jobs_per_user
+                && let Ok(ctx) = self.context_manager.get_context(job_id).await
+            {
+                let user_blocking = self
+                    .context_manager
+                    .parallel_blocking_count_for(&ctx.user_id)
+                    .await;
+                if user_blocking >= max_per_user {
+                    return Err(JobError::MaxJobsExceeded { max: max_per_user });
+                }
+            }
+
            // Transition job to in_progress
            self.context_manager
                .update_context(job_id, |ctx| {
@@ -784,8 +798,11 @@ mod tests {
            max_tool_iterations: 10,
            auto_approve_tools: true,
            default_timezone: "UTC".to_string(),
+            max_jobs_per_user: None,
            max_tokens_per_job,
            multi_tenant: false,
+            max_llm_concurrent_per_user: None,
+            max_jobs_concurrent_per_user: None,
        };
        let cm = Arc::new(ContextManager::new(5));
        let llm: Arc<dyn LlmProvider> = Arc::new(StubLlm);
@@ -8,8 +8,8 @@ use chrono::{DateTime, Utc};
 use uuid::Uuid;

 use crate::context::{ContextManager, JobState};
-use crate::db::Database;
 use crate::error::RepairError;
+use crate::tenant::AdminScope;
 use crate::tools::{BuildRequirement, Language, SoftwareBuilder, SoftwareType, ToolRegistry};

 /// A job that has been detected as stuck.
@@ -69,7 +69,7 @@ pub struct DefaultSelfRepair {
    /// Jobs in `InProgress` longer than this are treated as stuck.
    stuck_threshold: Duration,
    max_repair_attempts: u32,
-    store: Option<Arc<dyn Database>>,
+    store: Option<AdminScope>,
    builder: Option<Arc<dyn SoftwareBuilder>>,
    tools: Option<Arc<ToolRegistry>>,
 }
@@ -91,8 +91,8 @@ impl DefaultSelfRepair {
        }
    }

-    /// Add a Store for tool failure tracking.
-    pub fn with_store(mut self, store: Arc<dyn Database>) -> Self {
+    /// Add an admin-scoped store for tool failure tracking.
+    pub fn with_store(mut self, store: AdminScope) -> Self {
        self.store = Some(store);
        self
    }
@@ -806,7 +806,7 @@ mod tests {
        // 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_store(crate::tenant::AdminScope::new(Arc::clone(&db)))
            .with_builder(
                Arc::clone(&builder) as Arc<dyn crate::tools::SoftwareBuilder>,
                tools,
@@ -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, generate_tool_call_id};
+use ironclaw_common::truncate_preview;

 /// A session containing one or more threads.
 #[derive(Debug, Clone, Serialize, Deserialize)]
@@ -449,6 +449,7 @@ impl Thread {
                        id: call_id.clone(),
                        name: tc.name.clone(),
                        arguments: tc.parameters.clone(),
+                        reasoning: None,
                    })
                    .collect();

@@ -522,7 +523,12 @@ impl Thread {
                            && let Some(ref tcs) = assistant_msg.tool_calls
                        {
                            for tc in tcs {
-                                turn.record_tool_call(&tc.name, tc.arguments.clone());
+                                turn.record_tool_call_with_reasoning(
+                                    &tc.name,
+                                    tc.arguments.clone(),
+                                    tc.reasoning.clone(),
+                                    Some(tc.id.clone()),
+                                );
                            }
                        }

@@ -602,6 +608,10 @@ pub struct Turn {
    pub completed_at: Option<DateTime<Utc>>,
    /// Error message (if failed).
    pub error: Option<String>,
+    /// Agent's reasoning narrative for this turn.
+    /// Cleaned via `clean_response` and sanitized through `SafetyLayer` before storage.
+    #[serde(default, skip_serializing_if = "Option::is_none")]
+    pub narrative: Option<String>,
    /// Transient image content parts for multimodal LLM input.
    /// Not serialized — images are only needed for the current LLM call.
    /// The text description in `user_input` persists for compaction/context.
@@ -621,6 +631,7 @@ impl Turn {
            started_at: Utc::now(),
            completed_at: None,
            error: None,
+            narrative: None,
            image_content_parts: Vec::new(),
        }
    }
@@ -656,6 +667,26 @@ impl Turn {
            parameters: params,
            result: None,
            error: None,
+            rationale: None,
+            tool_call_id: None,
+        });
+    }
+
+    /// Record a tool call with reasoning context.
+    pub fn record_tool_call_with_reasoning(
+        &mut self,
+        name: impl Into<String>,
+        params: serde_json::Value,
+        rationale: Option<String>,
+        tool_call_id: Option<String>,
+    ) {
+        self.tool_calls.push(TurnToolCall {
+            name: name.into(),
+            parameters: params,
+            result: None,
+            error: None,
+            rationale,
+            tool_call_id,
        });
    }

@@ -672,6 +703,60 @@ impl Turn {
            call.error = Some(error.into());
        }
    }
+
+    /// Record a tool result by tool_call_id, with fallback to first pending call.
+    pub fn record_tool_result_for(&mut self, tool_call_id: &str, result: serde_json::Value) {
+        if let Some(call) = self
+            .tool_calls
+            .iter_mut()
+            .find(|c| c.tool_call_id.as_deref() == Some(tool_call_id))
+        {
+            call.result = Some(result);
+        } else if let Some(call) = self
+            .tool_calls
+            .iter_mut()
+            .find(|c| c.result.is_none() && c.error.is_none())
+        {
+            tracing::debug!(
+                tool_call_id = %tool_call_id,
+                fallback_tool = %call.name,
+                "tool_call_id not found, falling back to first pending call"
+            );
+            call.result = Some(result);
+        } else {
+            tracing::warn!(
+                tool_call_id = %tool_call_id,
+                "Tool result dropped: no matching or pending tool call"
+            );
+        }
+    }
+
+    /// Record a tool error by tool_call_id, with fallback to first pending call.
+    pub fn record_tool_error_for(&mut self, tool_call_id: &str, error: impl Into<String>) {
+        if let Some(call) = self
+            .tool_calls
+            .iter_mut()
+            .find(|c| c.tool_call_id.as_deref() == Some(tool_call_id))
+        {
+            call.error = Some(error.into());
+        } else if let Some(call) = self
+            .tool_calls
+            .iter_mut()
+            .find(|c| c.result.is_none() && c.error.is_none())
+        {
+            tracing::debug!(
+                tool_call_id = %tool_call_id,
+                fallback_tool = %call.name,
+                "tool_call_id not found, falling back to first pending call"
+            );
+            call.error = Some(error.into());
+        } else {
+            tracing::warn!(
+                tool_call_id = %tool_call_id,
+                "Tool error dropped: no matching or pending tool call"
+            );
+        }
+    }
 }

 /// Record of a tool call made during a turn.
@@ -685,6 +770,12 @@ pub struct TurnToolCall {
    pub result: Option<serde_json::Value>,
    /// Error from the tool (if failed).
    pub error: Option<String>,
+    /// Agent's reasoning for choosing this tool.
+    #[serde(default, skip_serializing_if = "Option::is_none")]
+    pub rationale: Option<String>,
+    /// The tool_call_id from the LLM, for identity-based result matching.
+    #[serde(default, skip_serializing_if = "Option::is_none")]
+    pub tool_call_id: Option<String>,
 }

 #[cfg(test)]
@@ -1309,6 +1400,7 @@ mod tests {
            id: "call_0".to_string(),
            name: "search".to_string(),
            arguments: serde_json::json!({"q": "test"}),
+            reasoning: None,
        };
        let messages = vec![
            ChatMessage::user("Find test"),
@@ -1339,6 +1431,7 @@ mod tests {
            id: "call_0".to_string(),
            name: "http".to_string(),
            arguments: serde_json::json!({}),
+            reasoning: None,
        };
        let messages = vec![
            ChatMessage::user("Fetch URL"),
@@ -1404,11 +1497,13 @@ mod tests {
            id: "call_a".to_string(),
            name: "search".to_string(),
            arguments: serde_json::json!({"q": "data"}),
+            reasoning: None,
        };
        let tc2 = ToolCall {
            id: "call_b".to_string(),
            name: "write".to_string(),
            arguments: serde_json::json!({"path": "out.txt"}),
+            reasoning: None,
        };
        let messages = vec![
            ChatMessage::user("Find and save"),
@@ -1620,4 +1715,100 @@ mod tests {
        let merged = thread.drain_pending_messages().unwrap();
        assert_eq!(merged, "failed batch\nnew msg");
    }
+
+    #[test]
+    fn test_record_tool_result_for_by_id() {
+        let mut turn = Turn::new(0, "test");
+        turn.record_tool_call_with_reasoning(
+            "tool_a",
+            serde_json::json!({}),
+            None,
+            Some("id_a".into()),
+        );
+        turn.record_tool_call_with_reasoning(
+            "tool_b",
+            serde_json::json!({}),
+            None,
+            Some("id_b".into()),
+        );
+
+        // Record result for second tool by ID
+        turn.record_tool_result_for("id_b", serde_json::json!("result_b"));
+        assert!(turn.tool_calls[0].result.is_none());
+        assert_eq!(
+            turn.tool_calls[1].result.as_ref().unwrap(),
+            &serde_json::json!("result_b")
+        );
+    }
+
+    #[test]
+    fn test_record_tool_error_for_by_id() {
+        let mut turn = Turn::new(0, "test");
+        turn.record_tool_call_with_reasoning(
+            "tool_a",
+            serde_json::json!({}),
+            None,
+            Some("id_a".into()),
+        );
+        turn.record_tool_call_with_reasoning(
+            "tool_b",
+            serde_json::json!({}),
+            None,
+            Some("id_b".into()),
+        );
+
+        turn.record_tool_error_for("id_a", "failed");
+        assert_eq!(turn.tool_calls[0].error.as_deref(), Some("failed"));
+        assert!(turn.tool_calls[1].error.is_none());
+    }
+
+    #[test]
+    fn test_record_tool_result_for_fallback_to_pending() {
+        let mut turn = Turn::new(0, "test");
+        turn.record_tool_call_with_reasoning(
+            "tool_a",
+            serde_json::json!({}),
+            None,
+            Some("id_a".into()),
+        );
+        turn.record_tool_call_with_reasoning(
+            "tool_b",
+            serde_json::json!({}),
+            None,
+            Some("id_b".into()),
+        );
+
+        // First tool already has a result
+        turn.tool_calls[0].result = Some(serde_json::json!("done"));
+
+        // Unknown ID should fall back to first pending (tool_b)
+        turn.record_tool_result_for("unknown_id", serde_json::json!("fallback"));
+        assert_eq!(
+            turn.tool_calls[0].result.as_ref().unwrap(),
+            &serde_json::json!("done")
+        );
+        assert_eq!(
+            turn.tool_calls[1].result.as_ref().unwrap(),
+            &serde_json::json!("fallback")
+        );
+    }
+
+    #[test]
+    fn test_record_tool_result_for_no_pending_is_noop() {
+        let mut turn = Turn::new(0, "test");
+        turn.record_tool_call_with_reasoning(
+            "tool_a",
+            serde_json::json!({}),
+            None,
+            Some("id_a".into()),
+        );
+        turn.tool_calls[0].result = Some(serde_json::json!("done"));
+
+        // No pending calls, unknown ID — should be a no-op
+        turn.record_tool_result_for("unknown_id", serde_json::json!("lost"));
+        assert_eq!(
+            turn.tool_calls[0].result.as_ref().unwrap(),
+            &serde_json::json!("done")
+        );
+    }
 }
@@ -102,11 +102,30 @@ impl SessionManager {
    /// Resolve an external thread ID to an internal thread.
    ///
    /// Returns the session and thread ID. Creates both if they don't exist.
+    /// Delegates to [`resolve_thread_with_parsed_uuid`](Self::resolve_thread_with_parsed_uuid)
+    /// with `parsed_uuid: None`.
    pub async fn resolve_thread(
        &self,
        user_id: &str,
        channel: &str,
        external_thread_id: Option<&str>,
+    ) -> (Arc<Mutex<Session>>, Uuid) {
+        self.resolve_thread_with_parsed_uuid(user_id, channel, external_thread_id, None)
+            .await
+    }
+
+    /// Like [`resolve_thread`](Self::resolve_thread), but accepts a pre-parsed
+    /// UUID to skip redundant parsing when the caller has already validated
+    /// the external thread ID as a UUID (e.g. the approval routing path).
+    ///
+    /// Uses a single read-lock acquisition for both the key lookup and the UUID
+    /// adoption check to reduce contention under concurrent approval load.
+    pub async fn resolve_thread_with_parsed_uuid(
+        &self,
+        user_id: &str,
+        channel: &str,
+        external_thread_id: Option<&str>,
+        parsed_uuid: Option<Uuid>,
    ) -> (Arc<Mutex<Session>>, Uuid) {
        let session = self.get_or_create_session(user_id).await;

@@ -116,51 +135,65 @@ impl SessionManager {
            external_thread_id: external_thread_id.map(String::from),
        };

-        // Check if we have a mapping
-        {
+        // Use pre-parsed UUID if available, otherwise parse from string.
+        let ext_uuid = parsed_uuid
+            .or_else(|| external_thread_id.and_then(|ext_tid| Uuid::parse_str(ext_tid).ok()));
+
+        // Validate that parsed_uuid (if provided) is consistent with external_thread_id.
+        #[cfg(debug_assertions)]
+        if let (Some(parsed), Some(ext_tid)) = (&parsed_uuid, external_thread_id) {
+            debug_assert_eq!(
+                Uuid::parse_str(ext_tid).ok().as_ref(),
+                Some(parsed),
+                "parsed_uuid must be the parsed form of external_thread_id"
+            );
+        }
+
+        // Single read lock for both the key lookup and UUID adoption check
+        let adoptable_uuid = {
            let thread_map = self.thread_map.read().await;
+
+            // Fast path: exact key match
            if let Some(&thread_id) = thread_map.get(&key) {
-                // Verify thread still exists in session
                let sess = session.lock().await;
                if sess.threads.contains_key(&thread_id) {
                    return (Arc::clone(&session), thread_id);
                }
            }
-        }

-        // Check if external_thread_id is itself a known thread UUID that
-        // exists in the session but was never registered in the thread_map
-        // (e.g. created by chat_new_thread_handler or hydrated from DB).
-        // We only adopt it if no thread_map entry maps to this UUID —
-        // otherwise it belongs to a different channel scope.
-        if let Some(ext_tid) = external_thread_id
-            && let Ok(ext_uuid) = Uuid::parse_str(ext_tid)
-        {
-            let thread_map = self.thread_map.read().await;
-            let mapped_elsewhere = thread_map.values().any(|&v| v == ext_uuid);
-            drop(thread_map);
+            // UUID adoption check (still under the same read lock).
+            // If external_thread_id is a valid UUID not mapped elsewhere,
+            // it may be a thread created by chat_new_thread_handler or
+            // hydrated from DB that we can adopt.
+            // Only attempt adoption when external_thread_id is Some, preserving
+            // the invariant that None external_thread_id never triggers adoption.
+            if external_thread_id.is_some() {
+                ext_uuid.filter(|&uuid| !thread_map.values().any(|&v| v == uuid))
+            } else {
+                None
+            }
+        }; // Single read lock dropped here

-            if !mapped_elsewhere {
-                let sess = session.lock().await;
-                if sess.threads.contains_key(&ext_uuid) {
-                    drop(sess);
+        // If we found an adoptable UUID, verify it exists in session and acquire write lock
+        if let Some(ext_uuid) = adoptable_uuid {
+            let sess = session.lock().await;
+            if sess.threads.contains_key(&ext_uuid) {
+                drop(sess);

-                    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.
+                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 mapped elsewhere while unlocked, fall through to create new thread
            }
        }

@@ -909,6 +942,44 @@ mod tests {
        }
    }

+    #[tokio::test]
+    async fn test_resolve_thread_consolidates_read_path() {
+        // Verify that resolve_thread still correctly handles:
+        // 1. Fast path: key exists in thread_map
+        // 2. UUID adoption: external_thread_id is a UUID in session but not in map
+        // 3. New thread: neither path matches
+        use crate::agent::session::Thread;
+
+        let manager = SessionManager::new();
+
+        // Case 1: Normal resolution creates thread and maps it
+        let (session1, tid1) = manager
+            .resolve_thread("user1", "chan1", Some("ext-1"))
+            .await;
+        // Resolving again with same key should return same thread (fast path)
+        let (_, tid1_again) = manager
+            .resolve_thread("user1", "chan1", Some("ext-1"))
+            .await;
+        assert_eq!(tid1, tid1_again);
+
+        // Case 2: UUID adoption - insert a thread directly into session
+        let adopted_id = Uuid::new_v4();
+        {
+            let mut sess = session1.lock().await;
+            let thread = Thread::with_id(adopted_id, sess.id);
+            sess.threads.insert(adopted_id, thread);
+        }
+        // Resolve with the UUID as external_thread_id -- should adopt it
+        let (_, resolved) = manager
+            .resolve_thread("user1", "chan1", Some(&adopted_id.to_string()))
+            .await;
+        assert_eq!(resolved, adopted_id);
+
+        // Case 3: Different channel gets different thread
+        let (_, tid2) = manager.resolve_thread("user1", "chan2", None).await;
+        assert_ne!(tid1, tid2);
+    }
+
    #[tokio::test]
    async fn test_resolve_thread_finds_existing_session_thread_by_uuid() {
        use crate::agent::session::{Session, Thread};
@@ -947,4 +1018,88 @@ mod tests {
            "should have exactly 1 thread, not a duplicate"
        );
    }
+
+    #[tokio::test]
+    async fn test_resolve_thread_with_pre_parsed_uuid_adopts_thread() {
+        use crate::agent::session::Thread;
+
+        let manager = SessionManager::new();
+        let (session, _) = manager.resolve_thread("user1", "chan1", None).await;
+
+        // Manually insert a thread with a known UUID
+        let known_id = Uuid::new_v4();
+        {
+            let mut sess = session.lock().await;
+            let thread = Thread::with_id(known_id, sess.id);
+            sess.threads.insert(known_id, thread);
+        }
+
+        // Resolve with pre-parsed UUID -- should adopt it without re-parsing
+        let (_, resolved) = manager
+            .resolve_thread_with_parsed_uuid(
+                "user1",
+                "chan1",
+                Some(&known_id.to_string()),
+                Some(known_id),
+            )
+            .await;
+        assert_eq!(resolved, known_id);
+    }
+
+    #[tokio::test]
+    async fn test_resolve_thread_with_parsed_uuid_none_delegates_to_parse() {
+        use crate::agent::session::Thread;
+
+        let manager = SessionManager::new();
+        let (session, _) = manager.resolve_thread("user2", "chan2", None).await;
+
+        // Insert a thread with a known UUID
+        let known_id = Uuid::new_v4();
+        {
+            let mut sess = session.lock().await;
+            let thread = Thread::with_id(known_id, sess.id);
+            sess.threads.insert(known_id, thread);
+        }
+
+        // Resolve with parsed_uuid=None but a valid UUID string -- should
+        // fall back to parsing the string and still adopt the thread
+        let (_, resolved) = manager
+            .resolve_thread_with_parsed_uuid("user2", "chan2", Some(&known_id.to_string()), None)
+            .await;
+        assert_eq!(resolved, known_id);
+    }
+
+    #[tokio::test]
+    async fn test_resolve_thread_with_none_external_thread_id_does_not_adopt() {
+        use crate::agent::session::Thread;
+
+        let manager = SessionManager::new();
+        let (session, default_tid) = manager.resolve_thread("user3", "chan3", None).await;
+
+        // Manually insert a thread with a known UUID (simulating a thread
+        // created by chat_new_thread_handler)
+        let known_id = Uuid::new_v4();
+        {
+            let mut sess = session.lock().await;
+            let thread = Thread::with_id(known_id, sess.id);
+            sess.threads.insert(known_id, thread);
+        }
+
+        // Resolve with external_thread_id=None but parsed_uuid=Some.
+        // This should NOT adopt the UUID — the old code prevented adoption
+        // when external_thread_id was None, and we preserve that invariant.
+        let (_, resolved) = manager
+            .resolve_thread_with_parsed_uuid("user3", "chan3", None, Some(known_id))
+            .await;
+
+        // Should return the existing default thread, not the injected UUID
+        assert_eq!(
+            resolved, default_tid,
+            "should return existing default thread when external_thread_id is None"
+        );
+        assert_ne!(
+            resolved, known_id,
+            "should NOT adopt UUID when external_thread_id is None"
+        );
+    }
 }
@@ -92,6 +92,17 @@ impl SubmissionParser {
                args: vec![],
            };
        }
+        if lower == "/reasoning" || lower.starts_with("/reasoning ") {
+            let args: Vec<String> = trimmed
+                .split_whitespace()
+                .skip(1)
+                .map(|s| s.to_string())
+                .collect();
+            return Submission::SystemCommand {
+                command: "reasoning".to_string(),
+                args,
+            };
+        }
        if lower == "/restart" {
            tracing::debug!("[SubmissionParser::parse] Recognized /restart command");
            return Submission::SystemCommand {
@@ -16,12 +16,12 @@ use crate::agent::dispatcher::{
 };
 use crate::agent::session::{MAX_PENDING_MESSAGES, 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 ironclaw_common::truncate_preview;

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

@@ -175,6 +175,7 @@ impl Agent {
    pub(super) async fn process_user_input(
        &self,
        message: &IncomingMessage,
+        tenant: crate::tenant::TenantCtx,
        session: Arc<Mutex<Session>>,
        thread_id: Uuid,
        content: &str,
@@ -351,7 +352,7 @@ impl Agent {

        if let Some(intent) = self.router.route_command(&temp_message) {
            // Explicit command like /status, /job, /list - handle directly
-            return self.handle_job_or_command(intent, message).await;
+            return self.handle_job_or_command(intent, message, &tenant).await;
        }

        // Natural language goes through the agentic loop
@@ -462,7 +463,7 @@ impl Agent {

        // Run the agentic tool execution loop
        let result = self
-            .run_agentic_loop(message, session.clone(), thread_id, turn_messages)
+            .run_agentic_loop(message, tenant, session.clone(), thread_id, turn_messages)
            .await;

        // Re-acquire lock and check if interrupted
@@ -513,10 +514,10 @@ impl Agent {
                };

                thread.complete_turn(&response);
-                let (turn_number, tool_calls) = thread
+                let (turn_number, tool_calls, narrative) = thread
                    .turns
                    .last()
-                    .map(|t| (t.turn_number, t.tool_calls.clone()))
+                    .map(|t| (t.turn_number, t.tool_calls.clone(), t.narrative.clone()))
                    .unwrap_or_default();
                let _ = self
                    .channels
@@ -534,6 +535,7 @@ impl Agent {
                    &message.user_id,
                    turn_number,
                    &tool_calls,
+                    narrative.as_deref(),
                )
                .await;
                self.persist_assistant_response(
@@ -725,7 +727,9 @@ impl Agent {
    ///
    /// Stored between the user and assistant messages so that
    /// `build_turns_from_db_messages` can reconstruct the tool call history.
-    /// Content is a JSON array of tool call summaries.
+    /// Content is a JSON object: `{ "calls": [...], "narrative": "..." }`.
+    /// The `calls` array contains tool call summaries with optional `rationale`
+    /// and `tool_call_id` fields. Legacy rows may be plain JSON arrays.
    pub(super) async fn persist_tool_calls(
        &self,
        thread_id: Uuid,
@@ -733,6 +737,7 @@ impl Agent {
        user_id: &str,
        turn_number: usize,
        tool_calls: &[crate::agent::session::TurnToolCall],
+        narrative: Option<&str>,
    ) {
        if tool_calls.is_empty() {
            return;
@@ -767,11 +772,30 @@ impl Agent {
                if let Some(ref error) = tc.error {
                    obj["error"] = serde_json::Value::String(truncate_preview(error, 200));
                }
+                if let Some(ref rationale) = tc.rationale {
+                    obj["rationale"] = serde_json::Value::String(truncate_preview(rationale, 500));
+                }
+                if let Some(ref tool_call_id) = tc.tool_call_id {
+                    obj["tool_call_id"] =
+                        serde_json::Value::String(truncate_preview(tool_call_id, 128));
+                }
                obj
            })
            .collect();

-        let content = match serde_json::to_string(&summaries) {
+        // Wrap in an object with optional narrative so it can be reconstructed.
+        // safety: no byte-index slicing here; comment describes JSON shape
+        let wrapper = if let Some(n) = narrative {
+            serde_json::json!({
+                "narrative": truncate_preview(n, 1000),
+                "calls": summaries,
+            })
+        } else {
+            serde_json::json!({
+                "calls": summaries,
+            })
+        };
+        let content = match serde_json::to_string(&wrapper) {
            Ok(c) => c,
            Err(e) => {
                tracing::warn!("Failed to serialize tool calls: {}", e);
@@ -1104,9 +1128,12 @@ impl Agent {
                    && let Some(turn) = thread.last_turn_mut()
                {
                    if is_tool_error {
-                        turn.record_tool_error(result_content.clone());
+                        turn.record_tool_error_for(&pending.tool_call_id, result_content.clone());
                    } else {
-                        turn.record_tool_result(serde_json::json!(result_content));
+                        turn.record_tool_result_for(
+                            &pending.tool_call_id,
+                            serde_json::json!(result_content),
+                        );
                    }
                }
            }
@@ -1358,9 +1385,12 @@ impl Agent {
                        && let Some(turn) = thread.last_turn_mut()
                    {
                        if is_deferred_error {
-                            turn.record_tool_error(deferred_content.clone());
+                            turn.record_tool_error_for(&tc.id, deferred_content.clone());
                        } else {
-                            turn.record_tool_result(serde_json::json!(deferred_content));
+                            turn.record_tool_result_for(
+                                &tc.id,
+                                serde_json::json!(deferred_content),
+                            );
                        }
                    }
                }
@@ -1444,7 +1474,13 @@ impl Agent {

            // Continue the agentic loop (a tool was already executed this turn)
            let result = self
-                .run_agentic_loop(message, session.clone(), thread_id, context_messages)
+                .run_agentic_loop(
+                    message,
+                    self.tenant_ctx(&message.user_id).await,
+                    session.clone(),
+                    thread_id,
+                    context_messages,
+                )
                .await;

            // Handle the result
@@ -1459,10 +1495,10 @@ impl Agent {
                    let (response, suggestions) =
                        crate::agent::dispatcher::extract_suggestions(&response);
                    thread.complete_turn(&response);
-                    let (turn_number, tool_calls) = thread
+                    let (turn_number, tool_calls, narrative) = thread
                        .turns
                        .last()
-                        .map(|t| (t.turn_number, t.tool_calls.clone()))
+                        .map(|t| (t.turn_number, t.tool_calls.clone(), t.narrative.clone()))
                        .unwrap_or_default();
                    // User message already persisted at turn start; save tool calls then assistant response
                    self.persist_tool_calls(
@@ -1471,6 +1507,7 @@ impl Agent {
                        &message.user_id,
                        turn_number,
                        &tool_calls,
+                        narrative.as_deref(),
                    )
                    .await;
                    self.persist_assistant_response(
@@ -1816,7 +1853,20 @@ fn rebuild_chat_messages_from_db(
            "assistant" => result.push(ChatMessage::assistant(&msg.content)),
            "tool_calls" => {
                // Try to parse the enriched JSON and rebuild tool messages.
-                if let Ok(calls) = serde_json::from_str::<Vec<serde_json::Value>>(&msg.content) {
+                // Supports two formats:
+                // - Old: plain JSON array of tool call summaries
+                // - New: wrapped object { "calls": [...], "narrative": "..." }
+                let calls: Vec<serde_json::Value> =
+                    match serde_json::from_str::<serde_json::Value>(&msg.content) {
+                        Ok(serde_json::Value::Array(arr)) => arr,
+                        Ok(serde_json::Value::Object(obj)) => obj
+                            .get("calls")
+                            .and_then(|v| v.as_array())
+                            .cloned()
+                            .unwrap_or_default(),
+                        _ => Vec::new(),
+                    };
+                {
                    if calls.is_empty() {
                        continue;
                    }
@@ -1839,6 +1889,10 @@ fn rebuild_chat_messages_from_db(
                                    .get("parameters")
                                    .cloned()
                                    .unwrap_or(serde_json::json!({})),
+                                reasoning: c
+                                    .get("rationale")
+                                    .and_then(|v| v.as_str())
+                                    .map(String::from),
                            })
                            .collect();

@@ -1853,7 +1907,10 @@ fn rebuild_chat_messages_from_db(
                            let name = c["name"].as_str().unwrap_or("unknown").to_string();
                            let content = if let Some(err) = c.get("error").and_then(|v| v.as_str())
                            {
-                                format!("Error: {}", err)
+                                // Both wrapped (new) and legacy (plain) errors pass
+                                // through as-is. Legacy errors are already descriptive
+                                // (e.g. "Tool 'http' failed: timeout"), so no prefix needed.
+                                err.to_string()
                            } else if let Some(res) = c.get("result").and_then(|v| v.as_str()) {
                                res.to_string()
                            } else if let Some(preview) =
@@ -1939,13 +1996,38 @@ mod tests {

        assert_eq!(result[3].role, crate::llm::Role::Tool);
        assert_eq!(result[3].tool_call_id, Some("call_1".to_string()));
-        assert!(result[3].content.contains("Error: timeout"));
+        assert!(result[3].content.contains("timeout"));

        // final assistant
        assert_eq!(result[4].role, crate::llm::Role::Assistant);
        assert_eq!(result[4].content, "I found some results.");
    }

+    #[test]
+    fn test_rebuild_chat_messages_preserves_wrapped_tool_error() {
+        let wrapped_error =
+            "<tool_output name=\"http\">\nTool 'http' failed: timeout\n</tool_output>";
+        let tool_json = serde_json::json!([
+            {
+                "name": "http",
+                "call_id": "call_1",
+                "parameters": {"url": "https://example.com"},
+                "error": wrapped_error
+            }
+        ]);
+        let messages = vec![
+            make_db_msg("user", "Fetch example"),
+            make_db_msg("tool_calls", &tool_json.to_string()),
+        ];
+
+        let result = rebuild_chat_messages_from_db(&messages);
+
+        assert_eq!(result.len(), 3);
+        assert_eq!(result[2].role, crate::llm::Role::Tool);
+        assert_eq!(result[2].tool_call_id, Some("call_1".to_string()));
+        assert_eq!(result[2].content, wrapped_error);
+    }
+
    #[test]
    fn test_rebuild_chat_messages_legacy_tool_calls_skipped() {
        // Legacy format: no call_id field
@@ -312,13 +312,7 @@ impl AppBuilder {
            .create_provider(&self.config.llm.nearai.base_url, self.session.clone());

        // Register memory tools if database is available
-        let workspace_user_id = self
-            .config
-            .channels
-            .gateway
-            .as_ref()
-            .map(|gw| gw.user_id.as_str())
-            .unwrap_or("default");
+        let workspace_user_id = self.config.owner_id.as_str();
        let workspace = if let Some(ref db) = self.db {
            let emb_cache_config = EmbeddingCacheConfig {
                max_entries: self.config.embeddings.cache_size,
@@ -342,17 +336,12 @@ impl AppBuilder {
            ws = ws.with_memory_layers(self.config.workspace.memory_layers.clone());
            let ws = Arc::new(ws);

-            // Detect multi-tenant mode: when GATEWAY_USER_TOKENS is configured,
+            // Detect multi-tenant mode: when the database has registered users,
            // each authenticated user needs their own workspace scope. Use
            // WorkspacePool (which implements WorkspaceResolver) to create
            // per-user workspaces on demand instead of sharing the startup
            // workspace across all users.
-            let is_multi_tenant = self
-                .config
-                .channels
-                .gateway
-                .as_ref()
-                .is_some_and(|gw| gw.user_tokens.is_some());
+            let is_multi_tenant = db.has_any_users().await.unwrap_or(false);

            if is_multi_tenant {
                let pool = Arc::new(crate::channels::web::server::WorkspacePool::new(
@@ -265,6 +265,15 @@ impl OutgoingResponse {
    }
 }

+/// A single tool decision within a reasoning update.
+#[derive(Debug, Clone)]
+pub struct ToolDecision {
+    /// Tool name.
+    pub tool_name: String,
+    /// Agent's reasoning for choosing this tool.
+    pub rationale: String,
+}
+
 /// Status update types for showing agent activity.
 #[derive(Debug, Clone)]
 pub enum StatusUpdate {
@@ -333,6 +342,13 @@ pub enum StatusUpdate {
    },
    /// Suggested follow-up messages for the user.
    Suggestions { suggestions: Vec<String> },
+    /// Agent reasoning update (why it chose specific tools).
+    ReasoningUpdate {
+        /// Human-readable summary of the agent's decision.
+        narrative: String,
+        /// Per-tool decisions.
+        decisions: Vec<ToolDecision>,
+    },
    /// Per-turn token usage and cost summary (shown as subtle metadata).
    TurnCost {
        input_tokens: u64,
@@ -39,7 +39,7 @@ mod webhook_server;

 pub use channel::{
    AttachmentKind, Channel, ChannelSecretUpdater, IncomingAttachment, IncomingMessage,
-    MessageStream, OutgoingResponse, StatusUpdate, routing_target_from_metadata,
+    MessageStream, OutgoingResponse, StatusUpdate, ToolDecision, routing_target_from_metadata,
 };
 pub use http::{HttpChannel, HttpChannelState};
 pub use manager::ChannelManager;
@@ -122,18 +122,32 @@ impl RelayClient {
    /// 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 url = format!("{}/oauth/slack/auth", self.base_url);
+        tracing::trace!(relay_url = %url, "RelayClient::initiate_oauth: sending request");
        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))
+            .get(&url)
            .bearer_auth(self.api_key.expose_secret())
            .query(&query)
            .send()
            .await
-            .map_err(|e| RelayError::Network(e.to_string()))?;
+            .map_err(|e| {
+                tracing::warn!(
+                    relay_url = %url,
+                    error = %e,
+                    "RelayClient::initiate_oauth: network request failed"
+                );
+                RelayError::Network(e.to_string())
+            })?;
+        tracing::trace!(
+            relay_url = %url,
+            status = %resp.status(),
+            "RelayClient::initiate_oauth: received response"
+        );

        let status = resp.status();
        if status.is_redirection() {
@@ -224,20 +238,39 @@ impl RelayClient {
        method: &str,
        body: serde_json::Value,
    ) -> Result<serde_json::Value, RelayError> {
+        let url = format!("{}/proxy/{}/{}", self.base_url, provider, method);
+        tracing::trace!(
+            relay_url = %url,
+            provider = %provider,
+            method = %method,
+            "RelayClient::proxy_provider: sending request"
+        );
        let query: Vec<(&str, &str)> = vec![("team_id", team_id)];
        let resp = self
            .http
-            .post(format!("{}/proxy/{}/{}", self.base_url, provider, method))
+            .post(&url)
            .bearer_auth(self.api_key.expose_secret())
            .query(&query)
            .json(&body)
            .send()
            .await
-            .map_err(|e| RelayError::Network(e.to_string()))?;
+            .map_err(|e| {
+                tracing::warn!(
+                    relay_url = %url,
+                    error = %e,
+                    "RelayClient::proxy_provider: network request failed"
+                );
+                RelayError::Network(e.to_string())
+            })?;

        if !resp.status().is_success() {
            let status = resp.status().as_u16();
            let body = resp.text().await.unwrap_or_default();
+            tracing::warn!(
+                relay_url = %url,
+                status = status,
+                "RelayClient::proxy_provider: channel-relay returned error"
+            );
            return Err(RelayError::Api {
                status,
                message: body,
@@ -255,23 +288,45 @@ impl RelayClient {
    /// 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 url = format!("{}/relay/signing-secret", self.base_url);
+        tracing::trace!(
+            relay_url = %url,
+            "RelayClient::get_signing_secret: fetching signing secret"
+        );
        let resp = self
            .http
-            .get(format!("{}/relay/signing-secret", self.base_url))
+            .get(&url)
            .bearer_auth(self.api_key.expose_secret())
            .query(&[("team_id", team_id)])
            .send()
            .await
-            .map_err(|e| RelayError::Network(e.to_string()))?;
+            .map_err(|e| {
+                tracing::warn!(
+                    relay_url = %url,
+                    error = %e,
+                    "RelayClient::get_signing_secret: network request failed"
+                );
+                RelayError::Network(e.to_string())
+            })?;

        if !resp.status().is_success() {
            let status = resp.status().as_u16();
            let body = resp.text().await.unwrap_or_default();
+            tracing::warn!(
+                relay_url = %url,
+                status = status,
+                body = %body,
+                "RelayClient::get_signing_secret: channel-relay returned error"
+            );
            return Err(RelayError::Api {
                status,
                message: body,
            });
        }
+        tracing::trace!(
+            relay_url = %url,
+            "RelayClient::get_signing_secret: received successful response"
+        );

        let body: serde_json::Value = resp
            .json()
@@ -75,6 +75,7 @@ const SLASH_COMMANDS: &[&str] = &[
    "/suggest",
    "/thread",
    "/resume",
+    "/reasoning",
 ];

 /// Rustyline helper for slash-command tab completion.
@@ -430,6 +431,18 @@ impl ReplChannel {
            let _ = execute!(stderr, terminal::Clear(terminal::ClearType::FromCursorDown));
        }
    }
+
+    async fn finish_single_message_turn(&self) {
+        if self.single_message.is_none() {
+            return;
+        }
+
+        let tx = self.msg_tx.lock().ok().and_then(|mut guard| guard.take());
+        if let Some(tx) = tx {
+            let msg = IncomingMessage::new("repl", &self.user_id, "/quit");
+            let _ = tx.send(msg).await;
+        }
+    }
 }

 impl Default for ReplChannel {
@@ -479,7 +492,9 @@ impl Channel for ReplChannel {

    async fn start(&self) -> Result<MessageStream, ChannelError> {
        let (tx, rx) = mpsc::channel(32);
-        // Store tx so send_status can inject approval responses directly
+        // Approval prompts inject responses back through this sender.
+        // In single-message mode we keep it until the turn finishes, then
+        // drop it after enqueuing /quit so the receiver stream can close.
        if let Ok(mut guard) = self.msg_tx.lock() {
            *guard = Some(tx.clone());
        }
@@ -495,11 +510,10 @@ impl Channel for ReplChannel {

            // Single message mode: send it and return
            if let Some(msg) = single_message {
-                let incoming = IncomingMessage::new("repl", &user_id, &msg).with_timezone(&sys_tz);
+                let incoming = IncomingMessage::new("repl", &user_id, &msg)
+                    .with_metadata(serde_json::json!({ "single_message_mode": true }))
+                    .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", &user_id, "/quit"));
                return;
            }

@@ -662,6 +676,7 @@ impl Channel for ReplChannel {
            println!();
            println!();
            self.stdin_locked.store(false, Ordering::Relaxed);
+            self.finish_single_message_turn().await;
            return Ok(());
        }

@@ -680,6 +695,7 @@ impl Channel for ReplChannel {
        println!();
        // Unlock stdin so readline can resume
        self.stdin_locked.store(false, Ordering::Relaxed);
+        self.finish_single_message_turn().await;
        Ok(())
    }

@@ -779,6 +795,7 @@ impl Channel for ReplChannel {
                let msg_tx = Arc::clone(&self.msg_tx);
                let user_id = self.user_id.clone();
                let lock_flag = Arc::clone(&self.stdin_locked);
+                let single_message_mode = self.single_message.is_some();
                tokio::task::spawn_blocking(move || {
                    let action = run_approval_selector(allow_always).unwrap_or("n");
                    // Unlock stdin so readline can resume after approval
@@ -787,7 +804,12 @@ impl Channel for ReplChannel {
                        return;
                    };
                    if let Some(tx) = guard.as_ref() {
-                        let msg = IncomingMessage::new("repl", &user_id, action);
+                        let msg = if single_message_mode {
+                            IncomingMessage::new("repl", &user_id, action)
+                                .with_metadata(serde_json::json!({ "single_message_mode": true }))
+                        } else {
+                            IncomingMessage::new("repl", &user_id, action)
+                        };
                        let _ = tx.blocking_send(msg);
                    }
                });
@@ -841,6 +863,19 @@ impl Channel for ReplChannel {
            StatusUpdate::Suggestions { .. } => {
                // Suggestions are only rendered by the web gateway
            }
+            StatusUpdate::ReasoningUpdate {
+                narrative,
+                decisions,
+            } => {
+                if !narrative.is_empty() {
+                    let display = truncate_for_preview(&narrative, CLI_STATUS_MAX);
+                    eprintln!("  \x1b[94m\u{25B6} {display}\x1b[0m");
+                }
+                for d in &decisions {
+                    let display = truncate_for_preview(&d.rationale, CLI_STATUS_MAX);
+                    eprintln!("    \x1b[90m\u{2192} {}: {display}\x1b[0m", d.tool_name);
+                }
+            }
            StatusUpdate::TurnCost { .. } => {
                // Cost display is handled by the TUI channel
            }
@@ -875,6 +910,7 @@ impl Channel for ReplChannel {
 #[cfg(test)]
 mod tests {
    use futures::StreamExt;
+    use tokio::time::{Duration, timeout};

    use super::*;

@@ -883,16 +919,36 @@ mod tests {
        let repl = ReplChannel::with_message("hi".to_string());
        let mut stream = repl.start().await.expect("repl start should succeed");

-        let first = stream.next().await.expect("first message missing");
+        let first = timeout(Duration::from_secs(1), stream.next())
+            .await
+            .expect("timed out waiting for first message")
+            .expect("first message missing");
        assert_eq!(first.channel, "repl");
        assert_eq!(first.content, "hi");

-        let second = stream.next().await.expect("quit message missing");
+        assert!(
+            timeout(Duration::from_millis(100), stream.next())
+                .await
+                .is_err(),
+            "single-message mode should wait for the turn to finish before quitting"
+        );
+
+        repl.respond(&first, OutgoingResponse::text("done"))
+            .await
+            .expect("respond should succeed");
+
+        let second = timeout(Duration::from_secs(1), stream.next())
+            .await
+            .expect("timed out waiting for quit message")
+            .expect("quit message missing");
        assert_eq!(second.channel, "repl");
        assert_eq!(second.content, "/quit");

        assert!(
-            stream.next().await.is_none(),
+            timeout(Duration::from_secs(1), stream.next())
+                .await
+                .expect("timed out waiting for stream to close")
+                .is_none(),
            "stream should end after /quit"
        );
    }
@@ -317,6 +317,14 @@ impl LoadedChannel {
            .map(|f| f.webhook_secret_name())
            .unwrap_or_else(|| format!("{}_webhook_secret", self.channel.channel_name()))
    }
+
+    /// Whether the host should enforce generic webhook-secret validation.
+    pub fn webhook_secret_managed_by_host(&self) -> bool {
+        self.capabilities_file
+            .as_ref()
+            .map(|f| f.webhook_secret_managed_by_host())
+            .unwrap_or(true)
+    }
 }

 /// Results from loading multiple channels.
@@ -185,6 +185,19 @@ impl ChannelCapabilitiesFile {
            .and_then(|w| w.secret_name.clone())
            .unwrap_or_else(|| format!("{}_webhook_secret", self.name))
    }
+
+    /// Whether the host should enforce generic webhook-secret validation.
+    ///
+    /// Defaults to true. Channels can opt out when they validate the shared
+    /// secret themselves using provider-specific request body fields.
+    pub fn webhook_secret_managed_by_host(&self) -> bool {
+        self.capabilities
+            .channel
+            .as_ref()
+            .and_then(|c| c.webhook.as_ref())
+            .and_then(|w| w.managed_by_host)
+            .unwrap_or(true)
+    }
 }

 /// Schema for channel capabilities.
@@ -302,6 +315,14 @@ pub struct WebhookSchema {
    /// Secret name in secrets store for HMAC-SHA256 signing (Slack-style).
    #[serde(default)]
    pub hmac_secret_name: Option<String>,
+
+    /// Whether the host/router should enforce generic webhook-secret
+    /// validation before the channel sees the request.
+    ///
+    /// Default: true. Set to false when the provider sends the shared secret
+    /// in a provider-specific request field rather than the configured header.
+    #[serde(default)]
+    pub managed_by_host: Option<bool>,
 }

 /// Setup configuration schema.
@@ -611,6 +632,25 @@ mod tests {
            Some("X-Telegram-Bot-Api-Secret-Token")
        );
        assert_eq!(file.webhook_secret_name(), "telegram_webhook_secret");
+        assert!(file.webhook_secret_managed_by_host());
+    }
+
+    #[test]
+    fn test_webhook_schema_can_disable_host_managed_secret_validation() {
+        let json = r#"{
+            "name": "feishu",
+            "capabilities": {
+                "channel": {
+                    "webhook": {
+                        "secret_name": "feishu_verification_token",
+                        "managed_by_host": false
+                    }
+                }
+            }
+        }"#;
+
+        let file = ChannelCapabilitiesFile::from_json(json).unwrap();
+        assert!(!file.webhook_secret_managed_by_host());
    }

    #[test]
@@ -139,13 +139,18 @@ async fn register_channel(
    };

    let secret_header = loaded.webhook_secret_header().map(|s| s.to_string());
+    let host_webhook_secret = if loaded.webhook_secret_managed_by_host() {
+        webhook_secret.clone()
+    } else {
+        None
+    };

    let webhook_path = format!("/webhook/{}", channel_name);
    let endpoints = vec![RegisteredEndpoint {
        channel_name: channel_name.clone(),
        path: webhook_path,
        methods: vec!["POST".to_string()],
-        require_secret: webhook_secret.is_some(),
+        require_secret: host_webhook_secret.is_some(),
    }];

    let channel_arc = Arc::new(loaded.channel.with_owner_actor_id(owner_actor_id.clone()));
@@ -205,7 +210,7 @@ async fn register_channel(

    tracing::info!(
        channel = %channel_name,
-        has_webhook_secret = webhook_secret.is_some(),
+        has_webhook_secret = host_webhook_secret.is_some(),
        secret_header = ?secret_header,
        "Registering channel with router"
    );
@@ -214,7 +219,7 @@ async fn register_channel(
        .register(
            Arc::clone(&channel_arc),
            endpoints,
-            webhook_secret.clone(),
+            host_webhook_secret.clone(),
            secret_header,
        )
        .await;
@@ -392,8 +397,9 @@ pub async fn inject_channel_credentials(
 /// placeholders in URLs and headers, so this function fills config fields
 /// that map to secret names.
 ///
-/// Mapping: for a channel named "feishu", secrets `feishu_app_id` and
-/// `feishu_app_secret` are injected as config keys `app_id` and `app_secret`.
+/// Mapping: for a channel named "feishu", secrets `feishu_app_id`,
+/// `feishu_app_secret`, and `feishu_verification_token` are injected as config
+/// keys `app_id`, `app_secret`, and `verification_token`.
 async fn inject_channel_secrets_into_config(
    channel_name: &str,
    secrets_store: &Option<Arc<dyn SecretsStore + Send + Sync>>,
@@ -404,6 +410,7 @@ async fn inject_channel_secrets_into_config(
        "feishu" => &[
            ("app_id", "feishu_app_id"),
            ("app_secret", "feishu_app_secret"),
+            ("verification_token", "feishu_verification_token"),
        ],
        _ => return,
    };
@@ -3061,6 +3061,20 @@ fn status_to_wit(
        },
        // Suggestions and turn cost are web-gateway-only; skip for WASM channels
        StatusUpdate::Suggestions { .. } | StatusUpdate::TurnCost { .. } => return None,
+        StatusUpdate::ReasoningUpdate {
+            narrative,
+            decisions,
+        } => {
+            let mut msg = narrative.clone();
+            for d in decisions {
+                msg.push_str(&format!("\n  → {}: {}", d.tool_name, d.rationale));
+            }
+            wit_channel::StatusUpdate {
+                status: wit_channel::StatusType::Status,
+                message: msg,
+                metadata_json,
+            }
+        }
    })
 }

@@ -91,6 +91,34 @@ Browser-facing HTTP API and SSE/WebSocket real-time streaming. Axum-based, singl
 | DELETE | `/api/routines/{id}` | Delete a routine |
 | GET | `/api/routines/{id}/runs` | List runs for a specific routine |

+### User Management (admin — requires `admin` role, see `docs/USER_MANAGEMENT_API.md`)
+| Method | Path | Description |
+|--------|------|-------------|
+| POST | `/api/admin/users` | Create a new user (returns one-time token) |
+| GET | `/api/admin/users` | List all users |
+| GET | `/api/admin/users/{id}` | Get a single user |
+| PATCH | `/api/admin/users/{id}` | Update user profile/metadata |
+| DELETE | `/api/admin/users/{id}` | Delete user and all data |
+| POST | `/api/admin/users/{id}/suspend` | Suspend a user |
+| POST | `/api/admin/users/{id}/activate` | Re-activate a user |
+| GET | `/api/admin/usage` | Per-user LLM usage stats |
+| GET | `/api/admin/users/{user_id}/secrets` | List a user's secrets (names only) |
+| PUT | `/api/admin/users/{user_id}/secrets/{name}` | Create or update a user's secret |
+| DELETE | `/api/admin/users/{user_id}/secrets/{name}` | Delete a user's secret |
+
+### Profile (self-service)
+| Method | Path | Description |
+|--------|------|-------------|
+| GET | `/api/profile` | Get own profile |
+| PATCH | `/api/profile` | Update own display name/metadata |
+
+### Tokens (self-service)
+| Method | Path | Description |
+|--------|------|-------------|
+| POST | `/api/tokens` | Create API token (returns plaintext once) |
+| GET | `/api/tokens` | List own tokens |
+| DELETE | `/api/tokens/{id}` | Revoke a token |
+
 ### Settings
 | Method | Path | Description |
 |--------|------|-------------|
@@ -5,6 +5,7 @@
 //! handlers can extract it via `AuthenticatedUser`.

 use std::collections::HashMap;
+use std::num::NonZeroUsize;

 use axum::{
    extract::{FromRequestParts, Request, State},
@@ -13,18 +14,25 @@ use axum::{
    response::{IntoResponse, Response},
 };
 use sha2::{Digest, Sha256};
+use std::sync::Arc;
+use std::time::Instant;
 use subtle::ConstantTimeEq;
+use tokio::sync::RwLock;
+
+use crate::db::Database;

 /// Identity resolved from a bearer token.
 #[derive(Debug, Clone)]
 pub struct UserIdentity {
    pub user_id: String,
+    /// `admin` or `member`.
+    pub role: String,
    /// Additional user scopes this identity can read from.
    pub workspace_read_scopes: Vec<String>,
 }

 /// Hash a token with SHA-256 for constant-size, timing-safe storage.
-fn hash_token(token: &str) -> [u8; 32] {
+pub fn hash_token(token: &str) -> [u8; 32] {
    let mut hasher = Sha256::new();
    hasher.update(token.as_bytes());
    hasher.finalize().into()
@@ -56,6 +64,7 @@ impl MultiAuthState {
                hash,
                UserIdentity {
                    user_id,
+                    role: "admin".to_string(),
                    workspace_read_scopes: Vec::new(),
                },
            )],
@@ -64,6 +73,11 @@ impl MultiAuthState {
    }

    /// Create a multi-user auth state from a map of tokens to identities.
+    ///
+    /// **Test-only** — production multi-user auth is DB-backed via
+    /// `DbAuthenticator`. This constructor is kept public (not `#[cfg(test)]`)
+    /// because integration tests in `tests/` compile the crate as a library
+    /// where `cfg(test)` is not set.
    pub fn multi(tokens: HashMap<String, UserIdentity>) -> Self {
        let hashed_tokens: Vec<([u8; 32], UserIdentity)> = tokens
            .into_iter()
@@ -108,6 +122,131 @@ impl MultiAuthState {
    }
 }

+/// DB-backed token authenticator with a bounded LRU cache.
+///
+/// Checks an LRU cache first (TTL 60s), then falls back to a DB query.
+/// The cache is bounded to `MAX_CACHE_ENTRIES` — when full, the least
+/// recently used entry is evicted regardless of TTL.
+///
+/// Revoking a token or suspending a user has at most 60s of stale
+/// authentication before the cache entry expires.
+#[derive(Clone)]
+#[allow(clippy::type_complexity)]
+pub struct DbAuthenticator {
+    store: Arc<dyn Database>,
+    /// Bounded LRU cache: token_hash → (identity, inserted_at).
+    cache: Arc<RwLock<lru::LruCache<[u8; 32], (UserIdentity, Instant)>>>,
+}
+
+impl DbAuthenticator {
+    /// Cache TTL — how long a successful auth is cached before re-querying the DB.
+    const CACHE_TTL_SECS: u64 = 60;
+    /// Maximum cache entries to prevent unbounded growth.
+    // SAFETY: 1024 is non-zero, so the unwrap in `new()` is infallible.
+    const MAX_CACHE_ENTRIES: NonZeroUsize = match NonZeroUsize::new(1024) {
+        Some(v) => v,
+        None => unreachable!(),
+    };
+
+    pub fn new(store: Arc<dyn Database>) -> Self {
+        Self {
+            store,
+            cache: Arc::new(RwLock::new(lru::LruCache::new(Self::MAX_CACHE_ENTRIES))),
+        }
+    }
+
+    /// Evict all cached entries for a specific user.
+    ///
+    /// Call this after security-critical actions (suspend, activate, role
+    /// change, token revocation) so the change takes effect immediately
+    /// instead of waiting for the 60-second TTL to expire.
+    pub async fn invalidate_user(&self, user_id: &str) {
+        let mut cache = self.cache.write().await;
+        // LruCache doesn't support predicate-based removal, so collect keys
+        // first then remove. The cache is bounded (1024) so this is cheap.
+        let keys_to_remove: Vec<[u8; 32]> = cache
+            .iter()
+            .filter(|(_, (identity, _))| identity.user_id == user_id)
+            .map(|(k, _)| *k)
+            .collect();
+        for key in keys_to_remove {
+            cache.pop(&key);
+        }
+    }
+
+    /// Authenticate a token against the database, using cache when possible.
+    ///
+    /// Returns `Ok(Some(identity))` on success, `Ok(None)` if the token is
+    /// not found, or `Err(())` if the database is unreachable (so the caller
+    /// can return 503 instead of 401).
+    pub async fn authenticate(&self, candidate: &str) -> Result<Option<UserIdentity>, ()> {
+        let hash = hash_token(candidate);
+
+        // Check cache first (promotes to most-recent on hit)
+        {
+            let mut cache = self.cache.write().await;
+            if let Some((identity, inserted_at)) = cache.get(&hash) {
+                if inserted_at.elapsed().as_secs() < Self::CACHE_TTL_SECS {
+                    return Ok(Some(identity.clone()));
+                }
+                // Expired — remove stale entry
+                cache.pop(&hash);
+            }
+        }
+
+        // Cache miss or expired — query DB
+        let (token_record, user_record) = match self.store.authenticate_token(&hash).await {
+            Ok(Some(pair)) => pair,
+            Ok(None) => return Ok(None),
+            Err(e) => {
+                tracing::warn!("DB auth lookup failed: {e}");
+                return Err(());
+            }
+        };
+
+        let identity = UserIdentity {
+            user_id: user_record.id.clone(),
+            role: user_record.role.clone(),
+            workspace_read_scopes: Vec::new(),
+        };
+
+        // Record token usage (best-effort, don't block auth)
+        let store = self.store.clone();
+        let token_id = token_record.id;
+        let user_id = user_record.id;
+        tokio::spawn(async move {
+            let _ = store.record_token_usage(token_id).await;
+            let _ = store.record_login(&user_id).await;
+        });
+
+        // Insert into bounded LRU — if full, least-recently-used entry is evicted
+        {
+            let mut cache = self.cache.write().await;
+            cache.put(hash, (identity.clone(), Instant::now()));
+        }
+
+        Ok(Some(identity))
+    }
+}
+
+/// Combined auth state: tries env-var tokens first, then DB-backed tokens.
+#[derive(Clone)]
+pub struct CombinedAuthState {
+    /// In-memory tokens from GATEWAY_AUTH_TOKEN.
+    pub env_auth: MultiAuthState,
+    /// DB-backed token authenticator (optional — only when a database is available).
+    pub db_auth: Option<DbAuthenticator>,
+}
+
+impl From<MultiAuthState> for CombinedAuthState {
+    fn from(env_auth: MultiAuthState) -> Self {
+        Self {
+            env_auth,
+            db_auth: None,
+        }
+    }
+}
+
 /// Axum extractor that provides the authenticated user identity.
 ///
 /// Only available on routes behind `auth_middleware`. Extracts the
@@ -130,6 +269,31 @@ where
    }
 }

+/// Axum extractor that requires the authenticated user to have the `admin` role.
+///
+/// Use instead of `AuthenticatedUser` on endpoints that modify system-wide
+/// state (user management, model selection, extension/skill installation).
+pub struct AdminUser(pub UserIdentity);
+
+impl<S> FromRequestParts<S> for AdminUser
+where
+    S: Send + Sync,
+{
+    type Rejection = (StatusCode, &'static str);
+
+    async fn from_request_parts(parts: &mut Parts, _state: &S) -> Result<Self, Self::Rejection> {
+        let identity = parts
+            .extensions
+            .get::<UserIdentity>()
+            .cloned()
+            .ok_or((StatusCode::UNAUTHORIZED, "Not authenticated"))?;
+        if identity.role != "admin" {
+            return Err((StatusCode::FORBIDDEN, "Admin role required"));
+        }
+        Ok(AdminUser(identity))
+    }
+}
+
 /// Whether query-string token auth is allowed for this request.
 ///
 /// Only GET requests to streaming endpoints may use `?token=xxx`. This
@@ -166,39 +330,65 @@ fn query_token(request: &Request) -> Option<String> {

 /// Auth middleware that validates bearer token from header or query param.
 ///
-/// SSE connections can't set headers from `EventSource`, so we also accept
-/// `?token=xxx` as a query parameter, but only on SSE/WS endpoints.
+/// Tries env-var tokens first (constant-time, in-memory), then falls back
+/// to DB-backed token lookup if configured. SSE connections can't set
+/// headers from `EventSource`, so we also accept `?token=xxx` as a query
+/// parameter, but only on SSE/WS endpoints.
 ///
 /// On successful authentication, inserts the matching `UserIdentity` into
 /// request extensions for downstream extraction via `AuthenticatedUser`.
 pub async fn auth_middleware(
-    State(auth): State<MultiAuthState>,
+    State(auth): State<CombinedAuthState>,
    headers: HeaderMap,
    mut request: Request,
    next: Next,
 ) -> Response {
-    // Try Authorization header first.
-    // RFC 6750 Section 2.1: auth-scheme comparison is case-insensitive.
+    // Extract the candidate token from header or query param.
+    let token = extract_token(&headers, &request);
+
+    if let Some(ref tok) = token {
+        // 1. Try env-var tokens first (fast, constant-time, in-memory).
+        if let Some(identity) = auth.env_auth.authenticate(tok) {
+            request.extensions_mut().insert(identity.clone());
+            return next.run(request).await;
+        }
+
+        // 2. Fall back to DB-backed token lookup.
+        if let Some(ref db_auth) = auth.db_auth {
+            match db_auth.authenticate(tok).await {
+                Ok(Some(identity)) => {
+                    request.extensions_mut().insert(identity);
+                    return next.run(request).await;
+                }
+                Err(()) => {
+                    return (StatusCode::SERVICE_UNAVAILABLE, "Database unavailable")
+                        .into_response();
+                }
+                Ok(None) => {}
+            }
+        }
+    }
+
+    (StatusCode::UNAUTHORIZED, "Invalid or missing auth token").into_response()
+}
+
+/// Extract a bearer token from the Authorization header or query parameter.
+fn extract_token(headers: &HeaderMap, request: &Request) -> Option<String> {
+    // Try Authorization header first (RFC 6750).
    if let Some(auth_header) = headers.get("authorization")
        && let Ok(value) = auth_header.to_str()
        && value.len() > 7
        && value[..7].eq_ignore_ascii_case("Bearer ")
-        && let Some(identity) = auth.authenticate(&value[7..])
    {
-        request.extensions_mut().insert(identity.clone());
-        return next.run(request).await;
+        return Some(value[7..].to_string());
    }

-    // Fall back to query parameter, but only for SSE/WS endpoints.
-    if allows_query_token_auth(&request)
-        && let Some(token) = query_token(&request)
-        && let Some(identity) = auth.authenticate(&token)
-    {
-        request.extensions_mut().insert(identity.clone());
-        return next.run(request).await;
+    // Fall back to query parameter for SSE/WS endpoints.
+    if allows_query_token_auth(request) {
+        return query_token(request);
    }

-    (StatusCode::UNAUTHORIZED, "Invalid or missing auth token").into_response()
+    None
 }

 #[cfg(test)]
@@ -227,6 +417,7 @@ mod tests {
            "tok-alice".to_string(),
            UserIdentity {
                user_id: "alice".to_string(),
+                role: "admin".to_string(),
                workspace_read_scopes: Vec::new(),
            },
        );
@@ -234,6 +425,7 @@ mod tests {
            "tok-bob".to_string(),
            UserIdentity {
                user_id: "bob".to_string(),
+                role: "admin".to_string(),
                workspace_read_scopes: Vec::new(),
            },
        );
@@ -274,7 +466,10 @@ mod tests {
    /// Router with streaming endpoints (query auth allowed) and regular
    /// endpoints (query auth rejected).
    fn test_app(token: &str) -> Router {
-        let state = MultiAuthState::single(token.to_string(), "test-user".to_string());
+        let state = CombinedAuthState::from(MultiAuthState::single(
+            token.to_string(),
+            "test-user".to_string(),
+        ));
        Router::new()
            .route("/api/chat/events", get(dummy_handler))
            .route("/api/logs/events", get(dummy_handler))
@@ -486,7 +681,7 @@ mod tests {

    /// Build a multi-user router where each token maps to a distinct identity.
    fn multi_user_app(tokens: HashMap<String, UserIdentity>) -> Router {
-        let state = MultiAuthState::multi(tokens);
+        let state = CombinedAuthState::from(MultiAuthState::multi(tokens));
        Router::new()
            .route("/api/chat/events", get(identity_handler))
            .route("/api/chat/send", post(identity_handler))
@@ -500,6 +695,7 @@ mod tests {
            "tok-alice".to_string(),
            UserIdentity {
                user_id: "alice".to_string(),
+                role: "admin".to_string(),
                workspace_read_scopes: vec!["shared".to_string()],
            },
        );
@@ -507,6 +703,7 @@ mod tests {
            "tok-bob".to_string(),
            UserIdentity {
                user_id: "bob".to_string(),
+                role: "admin".to_string(),
                workspace_read_scopes: vec!["shared".to_string(), "alice".to_string()],
            },
        );
@@ -643,7 +840,10 @@ mod tests {
    #[tokio::test]
    async fn test_multi_user_empty_scopes_for_single_user() {
        // Single-user mode creates identity with empty workspace_read_scopes.
-        let state = MultiAuthState::single("tok-only".to_string(), "solo".to_string());
+        let state = CombinedAuthState::from(MultiAuthState::single(
+            "tok-only".to_string(),
+            "solo".to_string(),
+        ));
        let app = Router::new()
            .route("/api/scopes", get(scopes_handler))
            .layer(middleware::from_fn_with_state(state, auth_middleware));
@@ -15,7 +15,9 @@ use crate::channels::IncomingMessage;
 use crate::channels::web::auth::AuthenticatedUser;
 use crate::channels::web::server::GatewayState;
 use crate::channels::web::types::*;
-use crate::channels::web::util::{build_turns_from_db_messages, truncate_preview};
+use crate::channels::web::util::{
+    build_turns_from_db_messages, tool_error_for_display, truncate_preview,
+};

 pub async fn chat_send_handler(
    State(state): State<Arc<GatewayState>>,
@@ -175,7 +177,7 @@ pub async fn chat_auth_token_handler(
            if result.verification.is_some() {
                state.sse.broadcast_for_user(
                    &user.user_id,
-                    SseEvent::AuthRequired {
+                    AppEvent::AuthRequired {
                        extension_name: req.extension_name.clone(),
                        instructions: Some(result.message),
                        auth_url: None,
@@ -187,7 +189,7 @@ pub async fn chat_auth_token_handler(

                state.sse.broadcast_for_user(
                    &user.user_id,
-                    SseEvent::AuthCompleted {
+                    AppEvent::AuthCompleted {
                        extension_name: req.extension_name.clone(),
                        success: true,
                        message: result.message,
@@ -202,7 +204,7 @@ pub async fn chat_auth_token_handler(
            if matches!(e, crate::extensions::ExtensionError::ValidationFailed(_)) {
                state.sse.broadcast_for_user(
                    &user.user_id,
-                    SseEvent::AuthRequired {
+                    AppEvent::AuthRequired {
                        extension_name: req.extension_name.clone(),
                        instructions: Some(msg.clone()),
                        auth_url: None,
@@ -397,9 +399,11 @@ pub async fn chat_history_handler(
                                };
                                truncate_preview(&s, 500)
                            }),
-                            error: tc.error.clone(),
+                            error: tc.error.as_deref().map(tool_error_for_display),
+                            rationale: tc.rationale.clone(),
                        })
                        .collect(),
+                    narrative: t.narrative.clone(),
                })
                .collect();

@@ -531,7 +535,7 @@ pub async fn chat_threads_handler(
    // Fallback: in-memory only (no assistant thread without DB)
    let sess = session.lock().await;
    let mut sorted_threads: Vec<_> = sess.threads.values().collect();
-    sorted_threads.sort_by(|a, b| b.updated_at.cmp(&a.updated_at));
+    sorted_threads.sort_by_key(|t| std::cmp::Reverse(t.updated_at));
    let threads: Vec<ThreadInfo> = sorted_threads
        .into_iter()
        .map(|t| ThreadInfo {
@@ -15,6 +15,14 @@ use crate::channels::web::auth::AuthenticatedUser;
 use crate::channels::web::server::GatewayState;
 use crate::channels::web::types::*;

+fn db_error(context: &str, e: impl std::fmt::Display) -> (StatusCode, String) {
+    tracing::error!(%e, context, "Database error in jobs handler");
+    (
+        StatusCode::INTERNAL_SERVER_ERROR,
+        "Internal database error".to_string(),
+    )
+}
+
 pub async fn jobs_list_handler(
    State(state): State<Arc<GatewayState>>,
    AuthenticatedUser(user): AuthenticatedUser,
@@ -213,10 +221,7 @@ pub async fn jobs_detail_handler(
        }
        Ok(None) => {}
        Err(e) => {
-            return Err((
-                StatusCode::INTERNAL_SERVER_ERROR,
-                format!("Database error: {}", e),
-            ));
+            return Err(db_error("jobs_handler", e));
        }
    }

@@ -257,10 +262,7 @@ pub async fn jobs_detail_handler(
            }))
        }
        Ok(None) => Err((StatusCode::NOT_FOUND, "Job not found".to_string())),
-        Err(e) => Err((
-            StatusCode::INTERNAL_SERVER_ERROR,
-            format!("Database error: {}", e),
-        )),
+        Err(e) => Err(db_error("jobs_handler", e)),
    }
 }

@@ -304,10 +306,7 @@ pub async fn jobs_cancel_handler(
            }
            Ok(None) => {}
            Err(e) => {
-                return Err((
-                    StatusCode::INTERNAL_SERVER_ERROR,
-                    format!("Database error: {}", e),
-                ));
+                return Err(db_error("jobs_handler", e));
            }
        }
    }
@@ -350,10 +349,7 @@ pub async fn jobs_cancel_handler(
            }
            Ok(None) => {}
            Err(e) => {
-                return Err((
-                    StatusCode::INTERNAL_SERVER_ERROR,
-                    format!("Database error: {}", e),
-                ));
+                return Err(db_error("jobs_handler", e));
            }
        }
    }
@@ -471,10 +467,7 @@ pub async fn jobs_restart_handler(
        }
        Ok(None) => {}
        Err(e) => {
-            return Err((
-                StatusCode::INTERNAL_SERVER_ERROR,
-                format!("Database error: {}", e),
-            ));
+            return Err(db_error("jobs_handler", e));
        }
    }

@@ -530,10 +523,7 @@ pub async fn jobs_restart_handler(
            })))
        }
        Ok(None) => Err((StatusCode::NOT_FOUND, "Job not found".to_string())),
-        Err(e) => Err((
-            StatusCode::INTERNAL_SERVER_ERROR,
-            format!("Database error: {}", e),
-        )),
+        Err(e) => Err(db_error("jobs_handler", e)),
    }
 }

@@ -609,10 +599,7 @@ pub async fn jobs_prompt_handler(
                return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
            }
            Err(e) => {
-                return Err((
-                    StatusCode::INTERNAL_SERVER_ERROR,
-                    format!("Database error: {}", e),
-                ));
+                return Err(db_error("jobs_handler", e));
            }
        }
    }
@@ -667,10 +654,7 @@ pub async fn jobs_events_handler(
            return Err((StatusCode::NOT_FOUND, "Job not found".to_string()));
        }
        Err(e) => {
-            return Err((
-                StatusCode::INTERNAL_SERVER_ERROR,
-                format!("Database error: {}", e),
-            ));
+            return Err(db_error("jobs_handler", e));
        }
    }

@@ -823,3 +807,17 @@ pub async fn job_files_read_handler(
        content,
    }))
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn test_db_error_does_not_leak_details() {
+        let (status, body) = db_error("test_context", "relation \"jobs\" does not exist");
+        assert_eq!(status, StatusCode::INTERNAL_SERVER_ERROR);
+        assert_eq!(body, "Internal database error");
+        assert!(!body.contains("relation"));
+        assert!(!body.contains("does not exist"));
+    }
+}
@@ -5,7 +5,10 @@
 pub mod jobs;
 pub mod memory;
 pub mod routines;
+pub mod secrets;
 pub mod skills;
+pub mod tokens;
+pub mod users;

 // Modules not yet wired into server.rs router -- suppress dead_code until
 // they replace their inline counterparts.
@@ -114,7 +114,7 @@ pub async fn routines_detail_handler(
            trigger_type: run.trigger_type.clone(),
            started_at: run.started_at.to_rfc3339(),
            completed_at: run.completed_at.map(|dt| dt.to_rfc3339()),
-            status: format!("{:?}", run.status),
+            status: run.status.to_string(),
            result_summary: run.result_summary.clone(),
            tokens_used: run.tokens_used,
            job_id: run.job_id,
@@ -324,7 +324,7 @@ pub async fn routines_runs_handler(
            trigger_type: run.trigger_type.clone(),
            started_at: run.started_at.to_rfc3339(),
            completed_at: run.completed_at.map(|dt| dt.to_rfc3339()),
-            status: format!("{:?}", run.status),
+            status: run.status.to_string(),
            result_summary: run.result_summary.clone(),
            tokens_used: run.tokens_used,
            job_id: run.job_id,
@@ -0,0 +1,183 @@
+//! Admin secrets provisioning handlers.
+//!
+//! Allows an admin (typically an application backend) to create, list, and
+//! delete secrets on behalf of individual users so their IronClaw agent can
+//! call back to external services with per-user credentials.
+
+use std::sync::Arc;
+
+use axum::{
+    Json,
+    extract::{Path, State},
+    http::StatusCode,
+};
+
+use crate::channels::web::auth::AdminUser;
+use crate::channels::web::server::GatewayState;
+use crate::secrets::CreateSecretParams;
+
+/// PUT /api/admin/users/{user_id}/secrets/{name} — create or update a secret.
+///
+/// Upserts: if a secret with the same (user_id, name) already exists it is
+/// overwritten. The plaintext value is encrypted at rest (AES-256-GCM) and
+/// never returned by any endpoint.
+pub async fn secrets_put_handler(
+    State(state): State<Arc<GatewayState>>,
+    AdminUser(_admin): AdminUser,
+    Path((user_id, name)): Path<(String, String)>,
+    Json(body): Json<serde_json::Value>,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let name = name.to_lowercase();
+
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+    store
+        .get_user(&user_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .ok_or((StatusCode::NOT_FOUND, "User not found".to_string()))?;
+
+    let secrets = state.secrets_store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Secrets store not available".to_string(),
+    ))?;
+
+    let value = body
+        .get("value")
+        .and_then(|v| v.as_str())
+        .ok_or((
+            StatusCode::BAD_REQUEST,
+            "Missing required field 'value'".to_string(),
+        ))?
+        .to_string();
+
+    let provider = body
+        .get("provider")
+        .and_then(|v| v.as_str())
+        .map(String::from);
+
+    let expires_in_days = body.get("expires_in_days").and_then(|v| v.as_u64());
+    if let Some(days) = expires_in_days
+        && days > 36500
+    {
+        return Err((
+            StatusCode::BAD_REQUEST,
+            "expires_in_days must be at most 36500".to_string(),
+        ));
+    }
+    let expires_at =
+        expires_in_days.map(|days| chrono::Utc::now() + chrono::Duration::days(days as i64));
+
+    let mut params = CreateSecretParams::new(name.clone(), value);
+    if let Some(p) = provider {
+        params = params.with_provider(p);
+    }
+    if let Some(exp) = expires_at {
+        params = params.with_expiry(exp);
+    }
+
+    let already_exists = secrets
+        .exists(&user_id, &name)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    secrets
+        .create(&user_id, params)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    Ok(Json(serde_json::json!({
+        "user_id": user_id,
+        "name": name,
+        "status": if already_exists { "updated" } else { "created" },
+    })))
+}
+
+/// GET /api/admin/users/{user_id}/secrets — list a user's secrets (names only).
+///
+/// Never returns secret values or hashes.
+pub async fn secrets_list_handler(
+    State(state): State<Arc<GatewayState>>,
+    AdminUser(_admin): AdminUser,
+    Path(user_id): Path<String>,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    // Verify the target user exists (consistent with PUT/DELETE).
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+    if store
+        .get_user(&user_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .is_none()
+    {
+        return Err((StatusCode::NOT_FOUND, "User not found".to_string()));
+    }
+
+    let secrets = state.secrets_store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Secrets store not available".to_string(),
+    ))?;
+
+    let refs = secrets
+        .list(&user_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    let secrets_json: Vec<serde_json::Value> = refs
+        .into_iter()
+        .map(|r| {
+            serde_json::json!({
+                "name": r.name,
+                "provider": r.provider,
+            })
+        })
+        .collect();
+
+    Ok(Json(serde_json::json!({
+        "user_id": user_id,
+        "secrets": secrets_json,
+    })))
+}
+
+/// DELETE /api/admin/users/{user_id}/secrets/{name} — delete a user's secret.
+pub async fn secrets_delete_handler(
+    State(state): State<Arc<GatewayState>>,
+    AdminUser(_admin): AdminUser,
+    Path((user_id, name)): Path<(String, String)>,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let name = name.to_lowercase();
+
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+    store
+        .get_user(&user_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .ok_or((StatusCode::NOT_FOUND, "User not found".to_string()))?;
+
+    let secrets = state.secrets_store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Secrets store not available".to_string(),
+    ))?;
+
+    let deleted = secrets
+        .delete(&user_id, &name)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    if !deleted {
+        return Err((StatusCode::NOT_FOUND, "Secret not found".to_string()));
+    }
+
+    Ok(Json(serde_json::json!({
+        "user_id": user_id,
+        "name": name,
+        "deleted": true,
+    })))
+}
@@ -0,0 +1,163 @@
+//! API token management handlers.
+
+use std::sync::Arc;
+
+use axum::{
+    Json,
+    extract::{Path, State},
+    http::StatusCode,
+};
+use rand::RngCore;
+use rand::rngs::OsRng;
+use uuid::Uuid;
+
+use crate::channels::web::auth::AuthenticatedUser;
+use crate::channels::web::server::GatewayState;
+
+/// POST /api/tokens — create a new API token (returns plaintext ONCE).
+pub async fn tokens_create_handler(
+    State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
+    Json(body): Json<serde_json::Value>,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    let name = body
+        .get("name")
+        .and_then(|v| v.as_str())
+        .map(|s| s.trim())
+        .filter(|s| !s.is_empty())
+        .ok_or((
+            StatusCode::BAD_REQUEST,
+            "Missing or empty 'name'".to_string(),
+        ))?
+        .to_string();
+
+    let expires_in_days: Option<i64> = match body.get("expires_in_days").and_then(|v| v.as_u64()) {
+        Some(d) if d > 36500 => {
+            return Err((
+                StatusCode::BAD_REQUEST,
+                "expires_in_days must not exceed 36500 (100 years)".to_string(),
+            ));
+        }
+        Some(d) => Some(d as i64),
+        None => None,
+    };
+
+    let expires_at = expires_in_days.map(|days| chrono::Utc::now() + chrono::Duration::days(days));
+
+    // Generate 32 random bytes for the token.
+    // Hash the hex-encoded plaintext (what the user sends as Bearer token),
+    // NOT the raw bytes — must match hash_token() in auth.rs.
+    let mut token_bytes = [0u8; 32];
+    OsRng.fill_bytes(&mut token_bytes);
+    let plaintext_token = hex::encode(token_bytes);
+    let hash = crate::channels::web::auth::hash_token(&plaintext_token);
+
+    // First 8 chars of the hex token as a prefix for identification.
+    let token_prefix = &plaintext_token[..8];
+
+    // Admin users can create tokens for other users via optional "user_id" field.
+    let target_user = body
+        .get("user_id")
+        .and_then(|v| v.as_str())
+        .filter(|_| user.role == "admin")
+        .unwrap_or(&user.user_id);
+
+    // Verify the target user exists to prevent orphan tokens.
+    if target_user != user.user_id {
+        store
+            .get_user(target_user)
+            .await
+            .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+            .ok_or((
+                StatusCode::NOT_FOUND,
+                format!("Target user '{target_user}' not found"),
+            ))?;
+    }
+
+    let record = store
+        .create_api_token(target_user, &name, &hash, token_prefix, expires_at)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    // Return the plaintext token — this is the ONLY time it is shown.
+    Ok(Json(serde_json::json!({
+        "token": plaintext_token,
+        "id": record.id.to_string(),
+        "name": record.name,
+        "token_prefix": record.token_prefix,
+        "expires_at": record.expires_at.map(|dt| dt.to_rfc3339()),
+        "created_at": record.created_at.to_rfc3339(),
+    })))
+}
+
+/// GET /api/tokens — list the current user's tokens (no hashes).
+pub async fn tokens_list_handler(
+    State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    let tokens = store
+        .list_api_tokens(&user.user_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    let tokens_json: Vec<serde_json::Value> = tokens
+        .into_iter()
+        .map(|t| {
+            serde_json::json!({
+                "id": t.id.to_string(),
+                "name": t.name,
+                "token_prefix": t.token_prefix,
+                "expires_at": t.expires_at.map(|dt| dt.to_rfc3339()),
+                "last_used_at": t.last_used_at.map(|dt| dt.to_rfc3339()),
+                "created_at": t.created_at.to_rfc3339(),
+                "revoked_at": t.revoked_at.map(|dt| dt.to_rfc3339()),
+            })
+        })
+        .collect();
+
+    Ok(Json(serde_json::json!({ "tokens": tokens_json })))
+}
+
+/// DELETE /api/tokens/{id} — revoke a token.
+pub async fn tokens_revoke_handler(
+    State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
+    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 token_id = Uuid::parse_str(&id)
+        .map_err(|_| (StatusCode::BAD_REQUEST, "Invalid token ID".to_string()))?;
+
+    let revoked = store
+        .revoke_api_token(token_id, &user.user_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    if !revoked {
+        return Err((StatusCode::NOT_FOUND, "Token not found".to_string()));
+    }
+
+    // Evict cached auth so revocation takes effect immediately.
+    if let Some(ref db_auth) = state.db_auth {
+        db_auth.invalidate_user(&user.user_id).await;
+    }
+
+    Ok(Json(serde_json::json!({
+        "status": "revoked",
+        "id": token_id.to_string(),
+    })))
+}
@@ -0,0 +1,534 @@
+//! User management API handlers (admin).
+
+use std::sync::Arc;
+
+use axum::{
+    Json,
+    extract::{Path, State},
+    http::StatusCode,
+};
+use rand::RngCore;
+use rand::rngs::OsRng;
+use uuid::Uuid;
+
+use crate::channels::web::auth::{AdminUser, AuthenticatedUser};
+use crate::channels::web::server::GatewayState;
+use crate::db::{Database, UserRecord};
+
+/// Check whether `user_id` is the sole active admin. Returns true if demoting,
+/// suspending, or deleting this user would leave zero admins.
+async fn is_last_admin(store: &dyn Database, user_id: &str) -> Result<bool, String> {
+    let users = store
+        .list_users(Some("active"))
+        .await
+        .map_err(|e| e.to_string())?;
+    let active_admins: Vec<_> = users.iter().filter(|u| u.role == "admin").collect();
+    Ok(active_admins.len() == 1 && active_admins[0].id == user_id)
+}
+
+/// POST /api/admin/users — create a new user.
+pub async fn users_create_handler(
+    State(state): State<Arc<GatewayState>>,
+    AdminUser(user): AdminUser,
+    Json(body): Json<serde_json::Value>,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    let display_name = body
+        .get("display_name")
+        .and_then(|v| v.as_str())
+        .map(|s| s.trim())
+        .filter(|s| !s.is_empty())
+        .ok_or((
+            StatusCode::BAD_REQUEST,
+            "Missing or empty 'display_name'".to_string(),
+        ))?
+        .to_string();
+
+    let email = body
+        .get("email")
+        .and_then(|v| v.as_str())
+        .map(|s| s.trim())
+        .filter(|s| !s.is_empty())
+        .map(String::from);
+    let role = body
+        .get("role")
+        .and_then(|v| v.as_str())
+        .unwrap_or("member")
+        .to_string();
+    if role != "admin" && role != "member" {
+        return Err((
+            StatusCode::BAD_REQUEST,
+            "role must be 'admin' or 'member'".to_string(),
+        ));
+    }
+
+    let user_id = Uuid::new_v4().to_string();
+
+    let now = chrono::Utc::now();
+    let user_record = UserRecord {
+        id: user_id.clone(),
+        email,
+        display_name: display_name.clone(),
+        status: "active".to_string(),
+        role,
+        created_at: now,
+        updated_at: now,
+        last_login_at: None,
+        created_by: Some(user.user_id.clone()),
+        metadata: serde_json::json!({}),
+    };
+
+    // Generate a first API token so the new user can authenticate immediately.
+    // Hash the hex-encoded plaintext (what the user sends as Bearer token),
+    // NOT the raw bytes — must match hash_token() in auth.rs.
+    let mut token_bytes = [0u8; 32];
+    OsRng.fill_bytes(&mut token_bytes);
+    let plaintext_token = hex::encode(token_bytes);
+    let token_hash = crate::channels::web::auth::hash_token(&plaintext_token);
+    let token_prefix = &plaintext_token[..8];
+
+    // Create user and initial token atomically — if either fails, both roll back.
+    let _token_record = store
+        .create_user_with_token(&user_record, "initial", &token_hash, token_prefix, None)
+        .await
+        .map_err(|e| {
+            let msg = e.to_string();
+            let lower = msg.to_ascii_lowercase();
+            if lower.contains("unique")
+                || lower.contains("duplicate")
+                || lower.contains("already exists")
+            {
+                (StatusCode::CONFLICT, msg)
+            } else {
+                (StatusCode::INTERNAL_SERVER_ERROR, msg)
+            }
+        })?;
+
+    Ok(Json(serde_json::json!({
+        "id": user_record.id,
+        "email": user_record.email,
+        "display_name": user_record.display_name,
+        "status": user_record.status,
+        "role": user_record.role,
+        "token": plaintext_token,
+        "created_at": user_record.created_at.to_rfc3339(),
+        "created_by": user_record.created_by,
+    })))
+}
+
+/// GET /api/admin/users — list all users with inline usage stats.
+pub async fn users_list_handler(
+    State(state): State<Arc<GatewayState>>,
+    AdminUser(_user): AdminUser,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    let users = store
+        .list_users(None)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    // Fetch per-user summary stats from DB (agent_jobs + llm_calls).
+    let summary_stats = store
+        .user_summary_stats(None)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    let stats_map: std::collections::HashMap<String, _> = summary_stats
+        .into_iter()
+        .map(|s| (s.user_id.clone(), s))
+        .collect();
+
+    let mut users_json: Vec<serde_json::Value> = Vec::with_capacity(users.len());
+    for u in users {
+        let db_stats = stats_map.get(&u.id);
+        let total_cost = db_stats.map_or(rust_decimal::Decimal::ZERO, |s| s.total_cost);
+
+        // Last active: prefer DB timestamp, fall back to last_login_at.
+        let last_active = db_stats.and_then(|s| s.last_active_at).or(u.last_login_at);
+
+        users_json.push(serde_json::json!({
+            "id": u.id,
+            "email": u.email,
+            "display_name": u.display_name,
+            "status": u.status,
+            "role": u.role,
+            "created_at": u.created_at.to_rfc3339(),
+            "updated_at": u.updated_at.to_rfc3339(),
+            "last_login_at": u.last_login_at.map(|dt| dt.to_rfc3339()),
+            "created_by": u.created_by,
+            "job_count": db_stats.map_or(0, |s| s.job_count),
+            "total_cost": total_cost.to_string(),
+            "last_active_at": last_active.map(|dt| dt.to_rfc3339()),
+        }));
+    }
+
+    Ok(Json(serde_json::json!({ "users": users_json })))
+}
+
+/// GET /api/admin/users/{id} — get a single user.
+pub async fn users_detail_handler(
+    State(state): State<Arc<GatewayState>>,
+    AdminUser(_user): AdminUser,
+    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 user_record = store
+        .get_user(&id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .ok_or((StatusCode::NOT_FOUND, "User not found".to_string()))?;
+
+    Ok(Json(serde_json::json!({
+        "id": user_record.id,
+        "email": user_record.email,
+        "display_name": user_record.display_name,
+        "status": user_record.status,
+        "role": user_record.role,
+        "created_at": user_record.created_at.to_rfc3339(),
+        "updated_at": user_record.updated_at.to_rfc3339(),
+        "last_login_at": user_record.last_login_at.map(|dt| dt.to_rfc3339()),
+        "created_by": user_record.created_by,
+        "metadata": user_record.metadata,
+    })))
+}
+
+/// PATCH /api/admin/users/{id} — update a user's profile.
+pub async fn users_update_handler(
+    State(state): State<Arc<GatewayState>>,
+    AdminUser(_user): AdminUser,
+    Path(id): Path<String>,
+    Json(body): Json<serde_json::Value>,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    // Verify the user exists.
+    let existing = store
+        .get_user(&id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .ok_or((StatusCode::NOT_FOUND, "User not found".to_string()))?;
+
+    let display_name = body
+        .get("display_name")
+        .and_then(|v| v.as_str())
+        .map(|s| s.trim())
+        .filter(|s| !s.is_empty())
+        .unwrap_or(&existing.display_name);
+
+    let metadata = if let Some(m) = body.get("metadata") {
+        if !m.is_object() {
+            return Err((
+                StatusCode::BAD_REQUEST,
+                "metadata must be a JSON object".to_string(),
+            ));
+        }
+        m
+    } else {
+        &existing.metadata
+    };
+
+    // Update role if provided and valid.
+    if let Some(role) = body.get("role").and_then(|v| v.as_str()) {
+        if role != "admin" && role != "member" {
+            return Err((
+                StatusCode::BAD_REQUEST,
+                "role must be 'admin' or 'member'".to_string(),
+            ));
+        }
+        if role != existing.role {
+            // Prevent demoting the last admin.
+            if existing.role == "admin"
+                && role == "member"
+                && is_last_admin(store.as_ref(), &id)
+                    .await
+                    .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e))?
+            {
+                return Err((
+                    StatusCode::CONFLICT,
+                    "Cannot demote the last admin".to_string(),
+                ));
+            }
+            store
+                .update_user_role(&id, role)
+                .await
+                .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+            // Evict cached auth so role change takes effect immediately.
+            if let Some(ref db_auth) = state.db_auth {
+                db_auth.invalidate_user(&id).await;
+            }
+        }
+    }
+
+    store
+        .update_user_profile(&id, display_name, metadata)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    // Re-fetch the updated record to return consistent data.
+    let updated = store
+        .get_user(&id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .ok_or((StatusCode::NOT_FOUND, "User not found".to_string()))?;
+
+    Ok(Json(serde_json::json!({
+        "id": updated.id,
+        "email": updated.email,
+        "display_name": updated.display_name,
+        "status": updated.status,
+        "role": updated.role,
+        "created_at": updated.created_at.to_rfc3339(),
+        "updated_at": updated.updated_at.to_rfc3339(),
+        "metadata": updated.metadata,
+    })))
+}
+
+/// POST /api/admin/users/{id}/suspend — suspend a user.
+pub async fn users_suspend_handler(
+    State(state): State<Arc<GatewayState>>,
+    AdminUser(_user): AdminUser,
+    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(),
+    ))?;
+
+    // Verify the user exists.
+    store
+        .get_user(&id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .ok_or((StatusCode::NOT_FOUND, "User not found".to_string()))?;
+
+    // Prevent suspending the last admin.
+    if is_last_admin(store.as_ref(), &id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e))?
+    {
+        return Err((
+            StatusCode::CONFLICT,
+            "Cannot suspend the last admin".to_string(),
+        ));
+    }
+
+    store
+        .update_user_status(&id, "suspended")
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    // Evict cached auth so suspension takes effect immediately.
+    if let Some(ref db_auth) = state.db_auth {
+        db_auth.invalidate_user(&id).await;
+    }
+
+    Ok(Json(serde_json::json!({
+        "id": id,
+        "status": "suspended",
+    })))
+}
+
+/// POST /api/admin/users/{id}/activate — activate a user.
+pub async fn users_activate_handler(
+    State(state): State<Arc<GatewayState>>,
+    AdminUser(_user): AdminUser,
+    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(),
+    ))?;
+
+    // Verify the user exists.
+    store
+        .get_user(&id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .ok_or((StatusCode::NOT_FOUND, "User not found".to_string()))?;
+
+    store
+        .update_user_status(&id, "active")
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    // Evict cached auth so reactivation takes effect immediately.
+    if let Some(ref db_auth) = state.db_auth {
+        db_auth.invalidate_user(&id).await;
+    }
+
+    Ok(Json(serde_json::json!({
+        "id": id,
+        "status": "active",
+    })))
+}
+
+/// DELETE /api/admin/users/{id} — delete a user and all their data.
+pub async fn users_delete_handler(
+    State(state): State<Arc<GatewayState>>,
+    AdminUser(_user): AdminUser,
+    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(),
+    ))?;
+
+    // Prevent deleting the last admin.
+    if is_last_admin(store.as_ref(), &id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e))?
+    {
+        return Err((
+            StatusCode::CONFLICT,
+            "Cannot delete the last admin".to_string(),
+        ));
+    }
+
+    let deleted = store
+        .delete_user(&id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    if !deleted {
+        return Err((StatusCode::NOT_FOUND, "User not found".to_string()));
+    }
+
+    Ok(Json(serde_json::json!({
+        "id": id,
+        "deleted": true,
+    })))
+}
+
+/// GET /api/profile — get the authenticated user's own profile.
+pub async fn profile_get_handler(
+    State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    let record = store
+        .get_user(&user.user_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .ok_or((StatusCode::NOT_FOUND, "User not found".to_string()))?;
+
+    Ok(Json(serde_json::json!({
+        "id": record.id,
+        "email": record.email,
+        "display_name": record.display_name,
+        "status": record.status,
+        "role": record.role,
+        "created_at": record.created_at.to_rfc3339(),
+        "last_login_at": record.last_login_at.map(|dt| dt.to_rfc3339()),
+    })))
+}
+
+/// PATCH /api/profile — update the authenticated user's own profile.
+pub async fn profile_update_handler(
+    State(state): State<Arc<GatewayState>>,
+    AuthenticatedUser(user): AuthenticatedUser,
+    Json(body): Json<serde_json::Value>,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    let store = state.store.as_ref().ok_or((
+        StatusCode::SERVICE_UNAVAILABLE,
+        "Database not available".to_string(),
+    ))?;
+
+    let current = store
+        .get_user(&user.user_id)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
+        .ok_or((StatusCode::NOT_FOUND, "User not found".to_string()))?;
+
+    let display_name = body
+        .get("display_name")
+        .and_then(|v| v.as_str())
+        .map(|s| s.trim())
+        .filter(|s| !s.is_empty())
+        .unwrap_or(&current.display_name);
+    let metadata = if let Some(m) = body.get("metadata") {
+        if !m.is_object() {
+            return Err((
+                StatusCode::BAD_REQUEST,
+                "metadata must be a JSON object".to_string(),
+            ));
+        }
+        m
+    } else {
+        &current.metadata
+    };
+
+    store
+        .update_user_profile(&user.user_id, display_name, metadata)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    Ok(Json(serde_json::json!({
+        "id": user.user_id,
+        "display_name": display_name,
+        "updated": true,
+    })))
+}
+
+/// GET /api/admin/usage — per-user LLM usage stats.
+pub async fn usage_stats_handler(
+    State(state): State<Arc<GatewayState>>,
+    AdminUser(_user): AdminUser,
+    axum::extract::Query(params): axum::extract::Query<std::collections::HashMap<String, 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 user_id = params.get("user_id").map(|s| s.as_str());
+    let period = params.get("period").map(|s| s.as_str()).unwrap_or("day");
+    let since = match period {
+        "week" => chrono::Utc::now() - chrono::Duration::days(7),
+        "month" => chrono::Utc::now() - chrono::Duration::days(30),
+        _ => chrono::Utc::now() - chrono::Duration::days(1),
+    };
+
+    let stats = store
+        .user_usage_stats(user_id, since)
+        .await
+        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
+
+    let entries: Vec<serde_json::Value> = stats
+        .iter()
+        .map(|s| {
+            serde_json::json!({
+                "user_id": s.user_id,
+                "model": s.model,
+                "call_count": s.call_count,
+                "input_tokens": s.input_tokens,
+                "output_tokens": s.output_tokens,
+                "total_cost": s.total_cost.to_string(),
+            })
+        })
+        .collect();
+
+    Ok(Json(serde_json::json!({
+        "period": period,
+        "since": since.to_rfc3339(),
+        "usage": entries,
+    })))
+}
@@ -54,10 +54,48 @@ fn validate_webhook_secret(
 ///
 /// This endpoint is **public** (no gateway auth token required) but protected
 /// by the per-routine webhook secret sent via the `X-Webhook-Secret` header.
+///
+/// **Single-user/backward-compatible**: looks up routines by path across all
+/// users. Disabled in multi-tenant mode — use the user-scoped endpoint at
+/// `/api/webhooks/u/{user_id}/{path}` instead.
 pub async fn webhook_trigger_handler(
    State(state): State<Arc<GatewayState>>,
    Path(path): Path<String>,
    headers: HeaderMap,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    // In multi-tenant mode, reject unscoped webhooks to prevent cross-user
+    // routine triggering. The per-routine secret provides some protection,
+    // but tenant isolation requires scoping by user_id.
+    // Use workspace_pool as the multi-tenant indicator — it's only set when
+    // has_any_users() was true at startup (not just when a DB exists).
+    if state.workspace_pool.is_some() {
+        return Err((
+            StatusCode::GONE,
+            "Unscoped webhooks disabled in multi-tenant mode. Use /api/webhooks/u/{user_id}/{path} instead.".to_string(),
+        ));
+    }
+    fire_webhook_inner(state, &path, None, &headers).await
+}
+
+/// Handle incoming webhook POST to `/api/webhooks/u/{user_id}/{path}`.
+///
+/// User-scoped variant for multi-tenant deployments. The `user_id` in the URL
+/// restricts the routine lookup to that user only, preventing cross-user
+/// webhook triggering even when paths collide.
+pub async fn webhook_trigger_user_scoped_handler(
+    State(state): State<Arc<GatewayState>>,
+    Path((user_id, path)): Path<(String, String)>,
+    headers: HeaderMap,
+) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
+    fire_webhook_inner(state, &path, Some(&user_id), &headers).await
+}
+
+/// Shared webhook logic for both scoped and unscoped endpoints.
+async fn fire_webhook_inner(
+    state: Arc<GatewayState>,
+    path: &str,
+    user_id: Option<&str>,
+    headers: &HeaderMap,
 ) -> Result<Json<serde_json::Value>, (StatusCode, String)> {
    // Rate limit check
    if !state.webhook_rate_limiter.check() {
@@ -72,9 +110,9 @@ pub async fn webhook_trigger_handler(
        "Database not available".to_string(),
    ))?;

-    // Targeted query instead of loading all routines
+    // Targeted query — when user_id is provided, restrict to that user's routines
    let routine = store
-        .get_webhook_routine_by_path(&path)
+        .get_webhook_routine_by_path(path, user_id)
        .await
        .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?
        .ok_or((
@@ -99,7 +137,7 @@ pub async fn webhook_trigger_handler(
        ))?
    };

-    let run_id = engine.fire_webhook(routine.id, &path).await.map_err(|e| {
+    let run_id = engine.fire_webhook(routine.id, path).await.map_err(|e| {
        let status = match &e {
            crate::error::RoutineError::NotFound { .. } => StatusCode::NOT_FOUND,
            crate::error::RoutineError::Disabled { .. }
@@ -18,6 +18,7 @@ pub mod auth;
 pub(crate) mod handlers;
 pub mod log_layer;
 pub mod openai_compat;
+pub mod responses_api;
 pub mod server;
 pub mod sse;
 pub mod types;
@@ -55,17 +56,17 @@ use crate::workspace::Workspace;

 use self::log_layer::{LogBroadcaster, LogLevelHandle};

-use self::auth::MultiAuthState;
+use self::auth::{CombinedAuthState, DbAuthenticator, MultiAuthState};
 use self::server::GatewayState;
 use self::sse::SseManager;
-use self::types::SseEvent;
+use self::types::AppEvent;

 /// Web gateway channel implementing the Channel trait.
 pub struct GatewayChannel {
    config: GatewayConfig,
    state: Arc<GatewayState>,
-    /// Multi-user auth state (replaces bare auth_token).
-    auth: MultiAuthState,
+    /// Combined auth state: env-var tokens + optional DB-backed tokens.
+    auth: CombinedAuthState,
 }

 impl GatewayChannel {
@@ -73,7 +74,7 @@ impl GatewayChannel {
    ///
    /// If no auth token is configured, generates a random one and prints it.
    /// Builds a single-user `MultiAuthState` from the config.
-    pub fn new(config: GatewayConfig) -> Self {
+    pub fn new(config: GatewayConfig, owner_id: String) -> Self {
        let auth_token = config.auth_token.clone().unwrap_or_else(|| {
            use rand::RngCore;
            use rand::rngs::OsRng;
@@ -82,7 +83,10 @@ impl GatewayChannel {
            bytes.iter().map(|b| format!("{b:02x}")).collect()
        });

-        let auth = MultiAuthState::single(auth_token, config.user_id.clone());
+        let auth = CombinedAuthState {
+            env_auth: MultiAuthState::single(auth_token, owner_id.clone()),
+            db_auth: None,
+        };

        let state = Arc::new(GatewayState {
            msg_tx: tokio::sync::RwLock::new(None),
@@ -98,7 +102,7 @@ impl GatewayChannel {
            job_manager: None,
            prompt_queue: None,
            scheduler: None,
-            default_user_id: config.user_id.clone(),
+            owner_id,
            shutdown_tx: tokio::sync::RwLock::new(None),
            ws_tracker: Some(Arc::new(ws::WsConnectionTracker::new())),
            llm_provider: None,
@@ -112,45 +116,8 @@ impl GatewayChannel {
            routine_engine: Arc::new(tokio::sync::RwLock::new(None)),
            startup_time: std::time::Instant::now(),
            active_config: server::ActiveConfigSnapshot::default(),
-        });
-
-        Self {
-            config,
-            state,
-            auth,
-        }
-    }
-
-    /// Create a gateway channel with a pre-built multi-user auth state.
-    pub fn new_multi_auth(config: GatewayConfig, auth: MultiAuthState) -> Self {
-        let state = Arc::new(GatewayState {
-            msg_tx: tokio::sync::RwLock::new(None),
-            sse: Arc::new(SseManager::new()),
-            workspace: None,
-            workspace_pool: None,
-            session_manager: None,
-            log_broadcaster: None,
-            log_level_handle: None,
-            extension_manager: None,
-            tool_registry: None,
-            store: None,
-            job_manager: None,
-            prompt_queue: None,
-            scheduler: None,
-            default_user_id: config.user_id.clone(),
-            shutdown_tx: tokio::sync::RwLock::new(None),
-            ws_tracker: Some(Arc::new(ws::WsConnectionTracker::new())),
-            llm_provider: None,
-            skill_registry: None,
-            skill_catalog: None,
-            chat_rate_limiter: server::PerUserRateLimiter::new(30, 60),
-            oauth_rate_limiter: server::RateLimiter::new(10, 60),
-            registry_entries: Vec::new(),
-            cost_guard: None,
-            routine_engine: Arc::new(tokio::sync::RwLock::new(None)),
-            startup_time: std::time::Instant::now(),
-            webhook_rate_limiter: server::RateLimiter::new(10, 60),
-            active_config: server::ActiveConfigSnapshot::default(),
+            secrets_store: None,
+            db_auth: None,
        });

        Self {
@@ -177,7 +144,7 @@ impl GatewayChannel {
            job_manager: self.state.job_manager.clone(),
            prompt_queue: self.state.prompt_queue.clone(),
            scheduler: self.state.scheduler.clone(),
-            default_user_id: self.state.default_user_id.clone(),
+            owner_id: self.state.owner_id.clone(),
            shutdown_tx: tokio::sync::RwLock::new(None),
            ws_tracker: self.state.ws_tracker.clone(),
            llm_provider: self.state.llm_provider.clone(),
@@ -191,6 +158,8 @@ impl GatewayChannel {
            routine_engine: Arc::clone(&self.state.routine_engine),
            startup_time: self.state.startup_time,
            active_config: self.state.active_config.clone(),
+            secrets_store: self.state.secrets_store.clone(),
+            db_auth: self.state.db_auth.clone(),
        };
        mutate(&mut new_state);
        self.state = Arc::new(new_state);
@@ -238,6 +207,17 @@ impl GatewayChannel {
        self
    }

+    /// Enable DB-backed token authentication alongside env-var tokens.
+    pub fn with_db_auth(mut self, store: Arc<dyn Database>) -> Self {
+        let authenticator = DbAuthenticator::new(store);
+        // Share the same DbAuthenticator (and its cache) between the auth
+        // middleware and GatewayState so handlers can invalidate the cache
+        // on security-critical actions (suspend, role change, token revoke).
+        self.rebuild_state(|s| s.db_auth = Some(Arc::new(authenticator.clone())));
+        self.auth.db_auth = Some(authenticator);
+        self
+    }
+
    /// Inject the container job manager for sandbox operations.
    pub fn with_job_manager(mut self, jm: Arc<ContainerJobManager>) -> Self {
        self.rebuild_state(|s| s.job_manager = Some(jm));
@@ -308,6 +288,15 @@ impl GatewayChannel {
        self
    }

+    /// Inject the secrets store for admin secret provisioning.
+    pub fn with_secrets_store(
+        mut self,
+        store: Arc<dyn crate::secrets::SecretsStore + Send + Sync>,
+    ) -> Self {
+        self.rebuild_state(|s| s.secrets_store = Some(store));
+        self
+    }
+
    /// Inject the per-user workspace pool for multi-user mode.
    pub fn with_workspace_pool(mut self, pool: Arc<server::WorkspacePool>) -> Self {
        self.rebuild_state(|s| s.workspace_pool = Some(pool));
@@ -316,7 +305,7 @@ impl GatewayChannel {

    /// Get the first auth token (for printing to console on startup).
    pub fn auth_token(&self) -> &str {
-        self.auth.first_token().unwrap_or("")
+        self.auth.env_auth.first_token().unwrap_or("")
    }

    /// Get a reference to the shared gateway state (for the agent to push SSE events).
@@ -367,7 +356,7 @@ impl Channel for GatewayChannel {

        self.state.sse.broadcast_for_user(
            &msg.user_id,
-            SseEvent::Response {
+            AppEvent::Response {
                content: response.content,
                thread_id,
            },
@@ -386,11 +375,11 @@ impl Channel for GatewayChannel {
            .and_then(|v| v.as_str())
            .map(String::from);
        let event = match status {
-            StatusUpdate::Thinking(msg) => SseEvent::Thinking {
+            StatusUpdate::Thinking(msg) => AppEvent::Thinking {
                message: msg,
                thread_id: thread_id.clone(),
            },
-            StatusUpdate::ToolStarted { name } => SseEvent::ToolStarted {
+            StatusUpdate::ToolStarted { name } => AppEvent::ToolStarted {
                name,
                thread_id: thread_id.clone(),
            },
@@ -399,23 +388,23 @@ impl Channel for GatewayChannel {
                success,
                error,
                parameters,
-            } => SseEvent::ToolCompleted {
+            } => AppEvent::ToolCompleted {
                name,
                success,
                error,
                parameters,
                thread_id: thread_id.clone(),
            },
-            StatusUpdate::ToolResult { name, preview } => SseEvent::ToolResult {
+            StatusUpdate::ToolResult { name, preview } => AppEvent::ToolResult {
                name,
                preview,
                thread_id: thread_id.clone(),
            },
-            StatusUpdate::StreamChunk(content) => SseEvent::StreamChunk {
+            StatusUpdate::StreamChunk(content) => AppEvent::StreamChunk {
                content,
                thread_id: thread_id.clone(),
            },
-            StatusUpdate::Status(msg) => SseEvent::Status {
+            StatusUpdate::Status(msg) => AppEvent::Status {
                message: msg,
                thread_id: thread_id.clone(),
            },
@@ -423,7 +412,7 @@ impl Channel for GatewayChannel {
                job_id,
                title,
                browse_url,
-            } => SseEvent::JobStarted {
+            } => AppEvent::JobStarted {
                job_id,
                title,
                browse_url,
@@ -434,7 +423,7 @@ impl Channel for GatewayChannel {
                description,
                parameters,
                allow_always,
-            } => SseEvent::ApprovalNeeded {
+            } => AppEvent::ApprovalNeeded {
                request_id,
                tool_name,
                description,
@@ -448,7 +437,7 @@ impl Channel for GatewayChannel {
                instructions,
                auth_url,
                setup_url,
-            } => SseEvent::AuthRequired {
+            } => AppEvent::AuthRequired {
                extension_name,
                instructions,
                auth_url,
@@ -458,25 +447,39 @@ impl Channel for GatewayChannel {
                extension_name,
                success,
                message,
-            } => SseEvent::AuthCompleted {
+            } => AppEvent::AuthCompleted {
                extension_name,
                success,
                message,
            },
-            StatusUpdate::ImageGenerated { data_url, path } => SseEvent::ImageGenerated {
+            StatusUpdate::ImageGenerated { data_url, path } => AppEvent::ImageGenerated {
                data_url,
                path,
                thread_id: thread_id.clone(),
            },
-            StatusUpdate::Suggestions { suggestions } => SseEvent::Suggestions {
+            StatusUpdate::Suggestions { suggestions } => AppEvent::Suggestions {
                suggestions,
+                thread_id: thread_id.clone(),
+            },
+            StatusUpdate::ReasoningUpdate {
+                narrative,
+                decisions,
+            } => AppEvent::ReasoningUpdate {
+                narrative,
+                decisions: decisions
+                    .into_iter()
+                    .map(|d| crate::channels::web::types::ToolDecisionDto {
+                        tool_name: d.tool_name,
+                        rationale: d.rationale,
+                    })
+                    .collect(),
                thread_id,
            },
            StatusUpdate::TurnCost {
                input_tokens,
                output_tokens,
                cost_usd,
-            } => SseEvent::TurnCost {
+            } => AppEvent::TurnCost {
                input_tokens,
                output_tokens,
                cost_usd,
@@ -512,7 +515,7 @@ impl Channel for GatewayChannel {
        };
        self.state.sse.broadcast_for_user(
            user_id,
-            SseEvent::Response {
+            AppEvent::Response {
                content: response.content,
                thread_id,
            },
@@ -231,6 +231,7 @@ pub fn convert_messages(messages: &[OpenAiMessage]) -> Result<Vec<ChatMessage>,
                                name: tc.function.name.clone(),
                                arguments: serde_json::from_str(&tc.function.arguments)
                                    .unwrap_or(serde_json::Value::Object(Default::default())),
+                                reasoning: None,
                            })
                            .collect();
                        Ok(ChatMessage::assistant_with_tool_calls(
@@ -954,6 +955,7 @@ mod tests {
            id: "call_abc".to_string(),
            name: "search".to_string(),
            arguments: serde_json::json!({"query": "rust"}),
+            reasoning: None,
        }];

        let converted = convert_tool_calls_to_openai(&calls);
@@ -16,7 +16,7 @@ use axum::{
        IntoResponse,
        sse::{Event, KeepAlive, Sse},
    },
-    routing::{get, post},
+    routing::{get, post, put},
 };
 use serde::Deserialize;
 use sha2::{Digest, Sha256};
@@ -31,7 +31,7 @@ use crate::bootstrap::ironclaw_base_dir;
 use crate::channels::IncomingMessage;
 use crate::channels::relay::DEFAULT_RELAY_NAME;
 use crate::channels::web::auth::{
-    AuthenticatedUser, MultiAuthState, UserIdentity, auth_middleware,
+    AuthenticatedUser, CombinedAuthState, UserIdentity, auth_middleware,
 };
 use crate::channels::web::handlers::jobs::{
    job_files_list_handler, job_files_read_handler, jobs_cancel_handler, jobs_detail_handler,
@@ -290,7 +290,22 @@ impl WorkspacePool {
        }

        let ws = Arc::new(ws);
+
        cache.insert(identity.user_id.clone(), Arc::clone(&ws));
+
+        // Seed identity files after inserting into cache (so the lock can be
+        // dropped) but before returning, so callers see a seeded workspace.
+        // Drop the write lock explicitly before the async seed to avoid
+        // blocking other workspace lookups.
+        drop(cache);
+        if let Err(e) = ws.seed_if_empty().await {
+            tracing::warn!(
+                user_id = identity.user_id,
+                "Failed to seed workspace: {}",
+                e
+            );
+        }
+
        ws
    }
 }
@@ -345,8 +360,8 @@ pub struct GatewayState {
    pub job_manager: Option<Arc<ContainerJobManager>>,
    /// Prompt queue for Claude Code follow-up prompts.
    pub prompt_queue: Option<PromptQueue>,
-    /// Default user ID (fallback for non-request contexts like heartbeat/routines).
-    pub default_user_id: String,
+    /// Durable owner scope for persistence and unauthenticated callback flows.
+    pub owner_id: String,
    /// Shutdown signal sender.
    pub shutdown_tx: tokio::sync::RwLock<Option<oneshot::Sender<()>>>,
    /// WebSocket connection tracker.
@@ -376,6 +391,10 @@ pub struct GatewayState {
    pub startup_time: std::time::Instant,
    /// Snapshot of active (resolved) configuration for the frontend.
    pub active_config: ActiveConfigSnapshot,
+    /// Secrets store for admin secret provisioning.
+    pub secrets_store: Option<Arc<dyn crate::secrets::SecretsStore + Send + Sync>>,
+    /// DB auth cache for invalidation on security-critical actions.
+    pub db_auth: Option<Arc<crate::channels::web::auth::DbAuthenticator>>,
 }

 /// Start the gateway HTTP server.
@@ -384,7 +403,7 @@ pub struct GatewayState {
 pub async fn start_server(
    addr: SocketAddr,
    state: Arc<GatewayState>,
-    auth: MultiAuthState,
+    auth: CombinedAuthState,
 ) -> Result<SocketAddr, crate::error::ChannelError> {
    let listener = tokio::net::TcpListener::bind(addr).await.map_err(|e| {
        crate::error::ChannelError::StartupFailed {
@@ -412,6 +431,11 @@ pub async fn start_server(
        .route(
            "/api/webhooks/{path}",
            post(crate::channels::web::handlers::webhooks::webhook_trigger_handler),
+        )
+        // User-scoped webhook endpoint for multi-tenant isolation
+        .route(
+            "/api/webhooks/u/{user_id}/{path}",
+            post(crate::channels::web::handlers::webhooks::webhook_trigger_user_scoped_handler),
        );

    // Protected routes (require auth)
@@ -505,6 +529,57 @@ pub async fn start_server(
            "/api/settings/{key}",
            axum::routing::delete(settings_delete_handler),
        )
+        // User management (admin)
+        .route(
+            "/api/admin/users",
+            get(super::handlers::users::users_list_handler)
+                .post(super::handlers::users::users_create_handler),
+        )
+        .route(
+            "/api/admin/users/{id}",
+            get(super::handlers::users::users_detail_handler)
+                .patch(super::handlers::users::users_update_handler)
+                .delete(super::handlers::users::users_delete_handler),
+        )
+        .route(
+            "/api/admin/users/{id}/suspend",
+            post(super::handlers::users::users_suspend_handler),
+        )
+        .route(
+            "/api/admin/users/{id}/activate",
+            post(super::handlers::users::users_activate_handler),
+        )
+        // Admin secrets provisioning (per-user)
+        .route(
+            "/api/admin/users/{user_id}/secrets",
+            get(super::handlers::secrets::secrets_list_handler),
+        )
+        .route(
+            "/api/admin/users/{user_id}/secrets/{name}",
+            put(super::handlers::secrets::secrets_put_handler)
+                .delete(super::handlers::secrets::secrets_delete_handler),
+        )
+        // Usage reporting (admin)
+        .route(
+            "/api/admin/usage",
+            get(super::handlers::users::usage_stats_handler),
+        )
+        // User self-service profile
+        .route(
+            "/api/profile",
+            get(super::handlers::users::profile_get_handler)
+                .patch(super::handlers::users::profile_update_handler),
+        )
+        // Token management
+        .route(
+            "/api/tokens",
+            get(super::handlers::tokens::tokens_list_handler)
+                .post(super::handlers::tokens::tokens_create_handler),
+        )
+        .route(
+            "/api/tokens/{id}",
+            axum::routing::delete(super::handlers::tokens::tokens_revoke_handler),
+        )
        // Gateway control plane
        .route("/api/gateway/status", get(gateway_status_handler))
        // OpenAI-compatible API
@@ -513,6 +588,15 @@ pub async fn start_server(
            post(super::openai_compat::chat_completions_handler),
        )
        .route("/v1/models", get(super::openai_compat::models_handler))
+        // OpenAI Responses API (routes through the full agent loop)
+        .route(
+            "/v1/responses",
+            post(super::responses_api::create_response_handler),
+        )
+        .route(
+            "/v1/responses/{id}",
+            get(super::responses_api::get_response_handler),
+        )
        .route_layer(middleware::from_fn_with_state(
            auth_state.clone(),
            auth_middleware,
@@ -555,6 +639,7 @@ pub async fn start_server(
            axum::http::Method::GET,
            axum::http::Method::POST,
            axum::http::Method::PUT,
+            axum::http::Method::PATCH,
            axum::http::Method::DELETE,
        ])
        .allow_headers(AllowHeaders::list([
@@ -569,6 +654,33 @@ pub async fn start_server(
        .merge(projects)
        .merge(protected)
        .layer(DefaultBodyLimit::max(10 * 1024 * 1024)) // 10 MB max request body (image uploads)
+        .layer(tower_http::catch_panic::CatchPanicLayer::custom(
+            |panic_info: Box<dyn std::any::Any + Send + 'static>| {
+                let detail = if let Some(s) = panic_info.downcast_ref::<String>() {
+                    s.clone()
+                } else if let Some(s) = panic_info.downcast_ref::<&str>() {
+                    (*s).to_string()
+                } else {
+                    "unknown panic".to_string()
+                };
+                // Truncate panic payload to avoid leaking sensitive data into logs.
+                // Use floor_char_boundary to avoid panicking on multi-byte UTF-8.
+                let safe_detail = if detail.len() > 200 {
+                    let end = detail.floor_char_boundary(200);
+                    format!("{}…", &detail[..end])
+                } else {
+                    detail
+                };
+                tracing::error!("Handler panicked: {}", safe_detail);
+                axum::http::Response::builder()
+                    .status(axum::http::StatusCode::INTERNAL_SERVER_ERROR)
+                    .header("content-type", "text/plain")
+                    .body(axum::body::Body::from("Internal Server Error"))
+                    .unwrap_or_else(|_| {
+                        axum::http::Response::new(axum::body::Body::from("Internal Server Error"))
+                    })
+            },
+        ))
        .layer(cors)
        .layer(SetResponseHeaderLayer::if_not_present(
            header::X_CONTENT_TYPE_OPTIONS,
@@ -775,7 +887,7 @@ async fn oauth_callback_handler(
                error = %error,
                "OAuth callback received with malformed state"
            );
-            clear_auth_mode(&state, &state.default_user_id).await;
+            clear_auth_mode(&state, &state.owner_id).await;
            return oauth_error_page("IronClaw");
        }
    };
@@ -811,7 +923,7 @@ async fn oauth_callback_handler(
        if let Some(ref sse) = flow.sse_manager {
            sse.broadcast_for_user(
                &flow.user_id,
-                SseEvent::AuthCompleted {
+                AppEvent::AuthCompleted {
                    extension_name: flow.extension_name.clone(),
                    success: false,
                    message: "OAuth flow expired. Please try again.".to_string(),
@@ -829,10 +941,10 @@ async fn oauth_callback_handler(

    let result: Result<(), String> = async {
        let token_response = if let Some(proxy_url) = &exchange_proxy_url {
-            let gateway_token = flow.gateway_token.as_deref().unwrap_or_default();
+            let oauth_proxy_auth_token = flow.oauth_proxy_auth_token().unwrap_or_default();
            oauth_defaults::exchange_via_proxy(oauth_defaults::ProxyTokenExchangeRequest {
                proxy_url,
-                gateway_token,
+                gateway_token: oauth_proxy_auth_token,
                token_url: &flow.token_url,
                client_id: &flow.client_id,
                client_secret: flow.client_secret.as_deref(),
@@ -949,11 +1061,11 @@ async fn oauth_callback_handler(
        message
    };

-    // Broadcast SSE event to notify the web UI
+    // Broadcast event to notify the web UI
    if let Some(ref sse) = flow.sse_manager {
        sse.broadcast_for_user(
            &flow.user_id,
-            SseEvent::AuthCompleted {
+            AppEvent::AuthCompleted {
                extension_name: flow.extension_name,
                success,
                message: final_message.clone(),
@@ -1136,7 +1248,7 @@ async fn slack_relay_oauth_callback_handler(
    let state_key = format!("relay:{}:oauth_state", DEFAULT_RELAY_NAME);
    let stored_state = match ext_mgr
        .secrets()
-        .get_decrypted(&state.default_user_id, &state_key)
+        .get_decrypted(&state.owner_id, &state_key)
        .await
    {
        Ok(secret) => secret.expose().to_string(),
@@ -1160,10 +1272,7 @@ async fn slack_relay_oauth_callback_handler(
    }

    // Delete the nonce (one-time use)
-    let _ = ext_mgr
-        .secrets()
-        .delete(&state.default_user_id, &state_key)
-        .await;
+    let _ = ext_mgr.secrets().delete(&state.owner_id, &state_key).await;

    let result: Result<(), String> = async {
        let store = state.store.as_ref().ok_or_else(|| {
@@ -1173,17 +1282,33 @@ async fn slack_relay_oauth_callback_handler(

        // Store team_id in settings
        let team_id_key = format!("relay:{}:team_id", DEFAULT_RELAY_NAME);
-        let _ = store
-            .set_setting(
-                &state.default_user_id,
-                &team_id_key,
-                &serde_json::json!(team_id),
-            )
-            .await;
+        tracing::info!(
+            relay = DEFAULT_RELAY_NAME,
+            owner_id = %state.owner_id,
+            team_id_key = %team_id_key,
+            "relay OAuth callback: storing team_id in settings"
+        );
+        store
+            .set_setting(&state.owner_id, &team_id_key, &serde_json::json!(team_id))
+            .await
+            .map_err(|e| {
+                tracing::error!(
+                    relay = DEFAULT_RELAY_NAME,
+                    owner_id = %state.owner_id,
+                    error = %e,
+                    "relay OAuth callback: failed to persist team_id to settings store"
+                );
+                format!("Failed to persist relay team_id: {e}")
+            })?;

        // Activate the relay channel
+        tracing::info!(
+            relay = DEFAULT_RELAY_NAME,
+            owner_id = %state.owner_id,
+            "relay OAuth callback: activating relay channel"
+        );
        ext_mgr
-            .activate_stored_relay(DEFAULT_RELAY_NAME, &state.default_user_id)
+            .activate_stored_relay(DEFAULT_RELAY_NAME, &state.owner_id)
            .await
            .map_err(|e| format!("Failed to activate relay channel: {}", e))?;

@@ -1202,8 +1327,8 @@ async fn slack_relay_oauth_callback_handler(
        }
    };

-    // Broadcast SSE event to notify the web UI
-    state.sse.broadcast(SseEvent::AuthCompleted {
+    // Broadcast event to notify the web UI
+    state.sse.broadcast(AppEvent::AuthCompleted {
        extension_name: DEFAULT_RELAY_NAME.to_string(),
        success,
        message: message.clone(),
@@ -1470,7 +1595,7 @@ async fn chat_auth_token_handler(
            if result.verification.is_some() {
                state.sse.broadcast_for_user(
                    &user.user_id,
-                    SseEvent::AuthRequired {
+                    AppEvent::AuthRequired {
                        extension_name: req.extension_name.clone(),
                        instructions: Some(result.message),
                        auth_url: None,
@@ -1483,7 +1608,7 @@ async fn chat_auth_token_handler(

                state.sse.broadcast_for_user(
                    &user.user_id,
-                    SseEvent::AuthCompleted {
+                    AppEvent::AuthCompleted {
                        extension_name: req.extension_name.clone(),
                        success: true,
                        message: result.message,
@@ -1492,7 +1617,7 @@ async fn chat_auth_token_handler(
            } else {
                state.sse.broadcast_for_user(
                    &user.user_id,
-                    SseEvent::AuthCompleted {
+                    AppEvent::AuthCompleted {
                        extension_name: req.extension_name.clone(),
                        success: false,
                        message: result.message,
@@ -1508,7 +1633,7 @@ async fn chat_auth_token_handler(
            if matches!(e, crate::extensions::ExtensionError::ValidationFailed(_)) {
                state.sse.broadcast_for_user(
                    &user.user_id,
-                    SseEvent::AuthRequired {
+                    AppEvent::AuthRequired {
                        extension_name: req.extension_name.clone(),
                        instructions: Some(msg.clone()),
                        auth_url: None,
@@ -1724,8 +1849,10 @@ async fn chat_history_handler(
                            truncate_preview(&s, 500)
                        }),
                        error: tc.error.clone(),
+                        rationale: tc.rationale.clone(),
                    })
                    .collect(),
+                narrative: t.narrative.clone(),
            })
            .collect();

@@ -1853,7 +1980,7 @@ async fn chat_threads_handler(

    // Fallback: in-memory only (no assistant thread without DB)
    let mut sorted_threads: Vec<_> = sess.threads.values().collect();
-    sorted_threads.sort_by(|a, b| b.updated_at.cmp(&a.updated_at));
+    sorted_threads.sort_by_key(|t| std::cmp::Reverse(t.updated_at));
    let threads: Vec<ThreadInfo> = sorted_threads
        .into_iter()
        .map(|t| ThreadInfo {
@@ -2173,6 +2300,11 @@ async fn extensions_activate_handler(
    AuthenticatedUser(user): AuthenticatedUser,
    Path(name): Path<String>,
 ) -> Result<Json<ActionResponse>, (StatusCode, String)> {
+    tracing::trace!(
+        extension = %name,
+        user_id = %user.user_id,
+        "extensions_activate_handler: received activate request"
+    );
    let ext_mgr = state.extension_manager.as_ref().ok_or((
        StatusCode::NOT_IMPLEMENTED,
        "Extension manager not available (secrets store required)".to_string(),
@@ -2180,6 +2312,10 @@ async fn extensions_activate_handler(

    match ext_mgr.activate(&name, &user.user_id).await {
        Ok(result) => {
+            tracing::info!(
+                extension = %name,
+                "extensions_activate_handler: activation succeeded"
+            );
            // Activation loaded the WASM module. Check if the tool needs
            // OAuth scope expansion (e.g., adding google-docs when gmail
            // already has a token but missing the documents scope).
@@ -2198,6 +2334,13 @@ async fn extensions_activate_handler(
                crate::extensions::ExtensionError::AuthRequired
            );

+            tracing::trace!(
+                extension = %name,
+                error = %activate_err,
+                needs_auth = needs_auth,
+                "extensions_activate_handler: activation failed, attempting auth fallback"
+            );
+
            if !needs_auth {
                return Ok(Json(ActionResponse::fail(activate_err.to_string())));
            }
@@ -2205,10 +2348,21 @@ async fn extensions_activate_handler(
            // Activation failed due to auth; try authenticating first.
            match ext_mgr.auth(&name, &user.user_id).await {
                Ok(auth_result) if auth_result.is_authenticated() => {
+                    tracing::trace!(
+                        extension = %name,
+                        "extensions_activate_handler: auth reports authenticated, retrying activate"
+                    );
                    // Auth succeeded, retry activation.
                    match ext_mgr.activate(&name, &user.user_id).await {
                        Ok(result) => Ok(Json(ActionResponse::ok(result.message))),
-                        Err(e) => Ok(Json(ActionResponse::fail(e.to_string()))),
+                        Err(e) => {
+                            tracing::warn!(
+                                extension = %name,
+                                error = %e,
+                                "extensions_activate_handler: retry after auth still failed"
+                            );
+                            Ok(Json(ActionResponse::fail(e.to_string())))
+                        }
                    }
                }
                Ok(auth_result) => {
@@ -2476,7 +2630,7 @@ async fn extensions_setup_submit_handler(
                // auth card or setup modal that was triggered by tool_auth/tool_activate.
                state.sse.broadcast_for_user(
                    &user.user_id,
-                    SseEvent::AuthCompleted {
+                    AppEvent::AuthCompleted {
                        extension_name: name.clone(),
                        success: result.activated,
                        message: resp.message.clone(),
@@ -2572,7 +2726,7 @@ async fn routines_runs_handler(
            trigger_type: run.trigger_type.clone(),
            started_at: run.started_at.to_rfc3339(),
            completed_at: run.completed_at.map(|dt| dt.to_rfc3339()),
-            status: format!("{:?}", run.status),
+            status: run.status.to_string(),
            result_summary: run.result_summary.clone(),
            tokens_used: run.tokens_used,
            job_id: run.job_id,
@@ -2976,7 +3130,7 @@ mod tests {
            store: None,
            job_manager: None,
            prompt_queue: None,
-            default_user_id: "test".to_string(),
+            owner_id: "test".to_string(),
            shutdown_tx: tokio::sync::RwLock::new(None),
            ws_tracker: None,
            llm_provider: None,
@@ -2991,6 +3145,8 @@ mod tests {
            routine_engine: Arc::new(tokio::sync::RwLock::new(None)),
            startup_time: std::time::Instant::now(),
            active_config: ActiveConfigSnapshot::default(),
+            secrets_store: None,
+            db_auth: None,
        })
    }

@@ -3001,6 +3157,160 @@ mod tests {
            .with_state(state)
    }

+    #[derive(Clone, Debug)]
+    struct RecordedOauthProxyRequest {
+        authorization: Option<String>,
+        form: std::collections::HashMap<String, String>,
+    }
+
+    #[derive(Clone)]
+    struct MockOauthProxyState {
+        requests: Arc<tokio::sync::Mutex<Vec<RecordedOauthProxyRequest>>>,
+    }
+
+    struct MockOauthProxyServer {
+        addr: std::net::SocketAddr,
+        requests: Arc<tokio::sync::Mutex<Vec<RecordedOauthProxyRequest>>>,
+        shutdown_tx: Option<tokio::sync::oneshot::Sender<()>>,
+        server_task: Option<tokio::task::JoinHandle<()>>,
+    }
+
+    impl MockOauthProxyServer {
+        async fn start() -> Self {
+            async fn exchange_handler(
+                State(state): State<MockOauthProxyState>,
+                headers: axum::http::HeaderMap,
+                axum::Form(form): axum::Form<std::collections::HashMap<String, String>>,
+            ) -> Json<serde_json::Value> {
+                state.requests.lock().await.push(RecordedOauthProxyRequest {
+                    authorization: headers
+                        .get(axum::http::header::AUTHORIZATION)
+                        .and_then(|value| value.to_str().ok())
+                        .map(str::to_string),
+                    form,
+                });
+                Json(serde_json::json!({
+                    "access_token": "proxy-access-token",
+                    "refresh_token": "proxy-refresh-token",
+                    "expires_in": 7200
+                }))
+            }
+
+            let requests = Arc::new(tokio::sync::Mutex::new(Vec::new()));
+            let listener = tokio::net::TcpListener::bind("127.0.0.1:0")
+                .await
+                .expect("bind mock oauth proxy");
+            let addr = listener.local_addr().expect("mock oauth proxy addr");
+            let app = Router::new()
+                .route("/oauth/exchange", post(exchange_handler))
+                .with_state(MockOauthProxyState {
+                    requests: Arc::clone(&requests),
+                });
+            let (shutdown_tx, shutdown_rx) = tokio::sync::oneshot::channel::<()>();
+            let server_task = tokio::spawn(async move {
+                let _ = axum::serve(listener, app)
+                    .with_graceful_shutdown(async {
+                        let _ = shutdown_rx.await;
+                    })
+                    .await;
+            });
+
+            Self {
+                addr,
+                requests,
+                shutdown_tx: Some(shutdown_tx),
+                server_task: Some(server_task),
+            }
+        }
+
+        fn base_url(&self) -> String {
+            format!("http://{}", self.addr)
+        }
+
+        async fn requests(&self) -> Vec<RecordedOauthProxyRequest> {
+            self.requests.lock().await.clone()
+        }
+
+        async fn shutdown(mut self) {
+            if let Some(tx) = self.shutdown_tx.take() {
+                let _ = tx.send(());
+            }
+            if let Some(task) = self.server_task.take() {
+                let _ = task.await;
+            }
+        }
+    }
+
+    impl Drop for MockOauthProxyServer {
+        fn drop(&mut self) {
+            if let Some(tx) = self.shutdown_tx.take() {
+                let _ = tx.send(());
+            }
+            if let Some(task) = self.server_task.take() {
+                task.abort();
+            }
+        }
+    }
+
+    struct EnvVarGuard {
+        key: &'static str,
+        original: Option<String>,
+    }
+
+    impl Drop for EnvVarGuard {
+        fn drop(&mut self) {
+            // SAFETY: Tests use lock_env() to serialize environment access.
+            unsafe {
+                if let Some(ref value) = self.original {
+                    std::env::set_var(self.key, value);
+                } else {
+                    std::env::remove_var(self.key);
+                }
+            }
+        }
+    }
+
+    fn set_env_var(key: &'static str, value: Option<&str>) -> EnvVarGuard {
+        let original = std::env::var(key).ok();
+        // SAFETY: Tests use lock_env() to serialize environment access.
+        unsafe {
+            if let Some(value) = value {
+                std::env::set_var(key, value);
+            } else {
+                std::env::remove_var(key);
+            }
+        }
+        EnvVarGuard { key, original }
+    }
+
+    fn fresh_pending_oauth_flow(
+        secrets: Arc<dyn crate::secrets::SecretsStore + Send + Sync>,
+        sse_manager: Option<Arc<SseManager>>,
+        oauth_proxy_auth_token: Option<String>,
+    ) -> crate::cli::oauth_defaults::PendingOAuthFlow {
+        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: Some("test-code-verifier".to_string()),
+            access_token_field: "access_token".to_string(),
+            secret_name: "test_token".to_string(),
+            provider: Some("google".to_string()),
+            validation_endpoint: None,
+            scopes: vec!["email".to_string()],
+            user_id: "test".to_string(),
+            secrets,
+            sse_manager,
+            gateway_token: oauth_proxy_auth_token,
+            token_exchange_extra_params: std::collections::HashMap::new(),
+            client_id_secret_name: None,
+            created_at: std::time::Instant::now(),
+        }
+    }
+
    #[tokio::test]
    async fn test_extensions_setup_submit_returns_failure_when_not_activated() {
        use axum::body::Body;
@@ -3057,6 +3367,7 @@ mod tests {
        // without needing the full auth middleware layer.
        req.extensions_mut().insert(UserIdentity {
            user_id: "test".to_string(),
+            role: "admin".to_string(),
            workspace_read_scopes: Vec::new(),
        });

@@ -3141,6 +3452,7 @@ mod tests {
        // without needing the full auth middleware layer.
        req.extensions_mut().insert(UserIdentity {
            user_id: "test".to_string(),
+            role: "admin".to_string(),
            workspace_read_scopes: Vec::new(),
        });

@@ -3167,7 +3479,7 @@ mod tests {
                Ok(Ok(scoped))
                    if matches!(
                        scoped.event,
-                        crate::channels::web::types::SseEvent::AuthRequired { .. }
+                        crate::channels::web::types::AppEvent::AuthRequired { .. }
                    ) =>
                {
                    panic!("verification responses should not emit auth_required SSE events")
@@ -3190,7 +3502,10 @@ mod tests {
        let state = test_gateway_state(None);

        let addr: SocketAddr = "127.0.0.1:0".parse().unwrap();
-        let auth = MultiAuthState::single("test-token".to_string(), "test".to_string());
+        let auth = CombinedAuthState::from(crate::channels::web::auth::MultiAuthState::single(
+            "test-token".to_string(),
+            "test".to_string(),
+        ));
        let bound = start_server(addr, state.clone(), auth)
            .await
            .expect("server should start");
@@ -3449,7 +3764,7 @@ mod tests {
        assert_eq!(resp.status(), StatusCode::OK);

        match receiver.recv().await.expect("auth_completed event").event {
-            crate::channels::web::types::SseEvent::AuthCompleted {
+            crate::channels::web::types::AppEvent::AuthCompleted {
                extension_name,
                success,
                message,
@@ -3658,6 +3973,284 @@ mod tests {
        );
    }

+    #[tokio::test]
+    async fn test_oauth_callback_accepts_versioned_hosted_state_without_instance_name() {
+        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 without instance 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_manager: 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", None);
+
+        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()
+        );
+    }
+
+    #[allow(clippy::await_holding_lock)]
+    #[tokio::test]
+    async fn test_oauth_callback_happy_path_with_gateway_token_fallback() {
+        use axum::body::Body;
+        use tower::ServiceExt;
+
+        let proxy = MockOauthProxyServer::start().await;
+        // Keep the process-wide env locked for the full callback so the handler
+        // sees a stable proxy URL/token configuration throughout the test.
+        let _env_guard = crate::config::helpers::lock_env();
+        let _exchange_url_guard =
+            set_env_var("IRONCLAW_OAUTH_EXCHANGE_URL", Some(&proxy.base_url()));
+        let _proxy_auth_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", None);
+        let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-test-token"));
+
+        let secrets = test_secrets_store();
+        let (ext_mgr, _wasm_tools_dir, _wasm_channels_dir) = test_ext_mgr(Arc::clone(&secrets));
+        let sse_mgr = Arc::new(SseManager::new());
+        let mut receiver = sse_mgr.sender().subscribe();
+        let flow = fresh_pending_oauth_flow(
+            Arc::clone(&secrets),
+            Some(Arc::clone(&sse_mgr)),
+            crate::cli::oauth_defaults::oauth_proxy_auth_token(),
+        );
+
+        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("Test Tool Connected"));
+
+        let requests = proxy.requests().await;
+        assert_eq!(requests.len(), 1);
+        assert_eq!(
+            requests[0].authorization.as_deref(),
+            Some("Bearer gateway-test-token")
+        );
+        assert_eq!(
+            requests[0].form.get("code").map(String::as_str),
+            Some("fake_code")
+        );
+        assert_eq!(
+            requests[0].form.get("code_verifier").map(String::as_str),
+            Some("test-code-verifier")
+        );
+
+        let access_token = secrets
+            .get_decrypted("test", "test_token")
+            .await
+            .expect("access token stored");
+        assert_eq!(access_token.expose(), "proxy-access-token");
+
+        let refresh_token = secrets
+            .get_decrypted("test", "test_token_refresh_token")
+            .await
+            .expect("refresh token stored");
+        assert_eq!(refresh_token.expose(), "proxy-refresh-token");
+
+        match receiver.recv().await.expect("auth_completed event").event {
+            crate::channels::web::types::AppEvent::AuthCompleted {
+                extension_name,
+                success,
+                ..
+            } => {
+                assert_eq!(extension_name, "test_tool");
+                assert!(success, "OAuth callback should broadcast success");
+            }
+            event => panic!("expected AuthCompleted event, got {event:?}"),
+        }
+
+        proxy.shutdown().await;
+    }
+
+    #[allow(clippy::await_holding_lock)]
+    #[tokio::test]
+    async fn test_oauth_callback_happy_path_with_dedicated_proxy_auth_token() {
+        use axum::body::Body;
+        use tower::ServiceExt;
+
+        let proxy = MockOauthProxyServer::start().await;
+        // Keep the process-wide env locked for the full callback so the handler
+        // sees a stable proxy URL/token configuration throughout the test.
+        let _env_guard = crate::config::helpers::lock_env();
+        let _exchange_url_guard =
+            set_env_var("IRONCLAW_OAUTH_EXCHANGE_URL", Some(&proxy.base_url()));
+        let _proxy_auth_guard = set_env_var(
+            "IRONCLAW_OAUTH_PROXY_AUTH_TOKEN",
+            Some("shared-oauth-proxy-secret"),
+        );
+        let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", None);
+
+        let secrets = test_secrets_store();
+        let (ext_mgr, _wasm_tools_dir, _wasm_channels_dir) = test_ext_mgr(Arc::clone(&secrets));
+        let sse_mgr = Arc::new(SseManager::new());
+        let mut receiver = sse_mgr.sender().subscribe();
+        let flow = fresh_pending_oauth_flow(
+            Arc::clone(&secrets),
+            Some(Arc::clone(&sse_mgr)),
+            crate::cli::oauth_defaults::oauth_proxy_auth_token(),
+        );
+
+        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", None);
+
+        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("Test Tool Connected"));
+
+        let requests = proxy.requests().await;
+        assert_eq!(requests.len(), 1);
+        assert_eq!(
+            requests[0].authorization.as_deref(),
+            Some("Bearer shared-oauth-proxy-secret")
+        );
+        assert_eq!(
+            requests[0].form.get("code").map(String::as_str),
+            Some("fake_code")
+        );
+        assert_eq!(
+            requests[0].form.get("code_verifier").map(String::as_str),
+            Some("test-code-verifier")
+        );
+
+        let access_token = secrets
+            .get_decrypted("test", "test_token")
+            .await
+            .expect("access token stored");
+        assert_eq!(access_token.expose(), "proxy-access-token");
+
+        let refresh_token = secrets
+            .get_decrypted("test", "test_token_refresh_token")
+            .await
+            .expect("refresh token stored");
+        assert_eq!(refresh_token.expose(), "proxy-refresh-token");
+
+        match receiver.recv().await.expect("auth_completed event").event {
+            crate::channels::web::types::AppEvent::AuthCompleted {
+                extension_name,
+                success,
+                ..
+            } => {
+                assert_eq!(extension_name, "test_tool");
+                assert!(success, "OAuth callback should broadcast success");
+            }
+            event => panic!("expected AuthCompleted event, got {event:?}"),
+        }
+
+        proxy.shutdown().await;
+    }
+
    // --- Slack relay OAuth CSRF tests ---

    fn test_relay_oauth_router(state: Arc<GatewayState>) -> Router {
@@ -11,7 +11,7 @@ use tokio::sync::broadcast;
 use tokio_stream::StreamExt;
 use tokio_stream::wrappers::BroadcastStream;

-use crate::channels::web::types::SseEvent;
+use crate::channels::web::types::AppEvent;

 /// Maximum number of concurrent SSE/WebSocket connections.
 /// Prevents resource exhaustion from connection flooding.
@@ -25,7 +25,7 @@ const MAX_CONNECTIONS: u64 = 100;
 #[derive(Debug, Clone)]
 pub(crate) struct ScopedEvent {
    pub(crate) user_id: Option<String>,
-    pub(crate) event: SseEvent,
+    pub(crate) event: AppEvent,
 }

 /// Manages SSE broadcast to all connected browser tabs.
@@ -75,7 +75,7 @@ impl SseManager {
    }

    /// Broadcast an event to all connected clients (global/unscoped).
-    pub fn broadcast(&self, event: SseEvent) {
+    pub fn broadcast(&self, event: AppEvent) {
        let _ = self.tx.send(ScopedEvent {
            user_id: None,
            event,
@@ -86,7 +86,7 @@ impl SseManager {
    ///
    /// Only subscribers for this user_id (or unscoped subscribers) will
    /// receive the event.
-    pub fn broadcast_for_user(&self, user_id: &str, event: SseEvent) {
+    pub fn broadcast_for_user(&self, user_id: &str, event: AppEvent) {
        let _ = self.tx.send(ScopedEvent {
            user_id: Some(user_id.to_string()),
            event,
@@ -108,7 +108,7 @@ impl SseManager {
    pub fn subscribe_raw(
        &self,
        user_id: Option<String>,
-    ) -> Option<impl Stream<Item = SseEvent> + Send + 'static + use<>> {
+    ) -> Option<impl Stream<Item = AppEvent> + Send + 'static + use<>> {
        // Atomically increment only if below the limit. This prevents
        // concurrent callers from overshooting max_connections.
        let counter = Arc::clone(&self.connection_count);
@@ -186,30 +186,7 @@ impl SseManager {
                        return None;
                    }
                };
-                let event_type = match &event {
-                    SseEvent::Response { .. } => "response",
-                    SseEvent::Thinking { .. } => "thinking",
-                    SseEvent::ToolStarted { .. } => "tool_started",
-                    SseEvent::ToolCompleted { .. } => "tool_completed",
-                    SseEvent::ToolResult { .. } => "tool_result",
-                    SseEvent::StreamChunk { .. } => "stream_chunk",
-                    SseEvent::Status { .. } => "status",
-                    SseEvent::ApprovalNeeded { .. } => "approval_needed",
-                    SseEvent::AuthRequired { .. } => "auth_required",
-                    SseEvent::AuthCompleted { .. } => "auth_completed",
-                    SseEvent::Error { .. } => "error",
-                    SseEvent::JobStarted { .. } => "job_started",
-                    SseEvent::JobMessage { .. } => "job_message",
-                    SseEvent::JobToolUse { .. } => "job_tool_use",
-                    SseEvent::JobToolResult { .. } => "job_tool_result",
-                    SseEvent::JobStatus { .. } => "job_status",
-                    SseEvent::JobResult { .. } => "job_result",
-                    SseEvent::Heartbeat => "heartbeat",
-                    SseEvent::ImageGenerated { .. } => "image_generated",
-                    SseEvent::Suggestions { .. } => "suggestions",
-                    SseEvent::TurnCost { .. } => "turn_cost",
-                    SseEvent::ExtensionStatus { .. } => "extension_status",
-                };
+                let event_type = event.event_type();
                Some(Ok(Event::default().event(event_type).data(data)))
            });

@@ -272,7 +249,7 @@ mod tests {
    fn test_broadcast_without_receivers() {
        let manager = SseManager::new();
        // Should not panic even with no receivers
-        manager.broadcast(SseEvent::Heartbeat);
+        manager.broadcast(AppEvent::Heartbeat);
    }

    #[tokio::test]
@@ -280,14 +257,14 @@ mod tests {
        let manager = SseManager::new();
        let mut stream = Box::pin(manager.subscribe_raw(None).expect("should subscribe"));

-        manager.broadcast(SseEvent::Status {
+        manager.broadcast(AppEvent::Status {
            message: "test".to_string(),
            thread_id: None,
        });

        let event = stream.next().await.unwrap();
        match event {
-            SseEvent::Status { message, .. } => assert_eq!(message, "test"),
+            AppEvent::Status { message, .. } => assert_eq!(message, "test"),
            _ => panic!("unexpected event type"),
        }
    }
@@ -299,14 +276,14 @@ mod tests {

        assert_eq!(manager.connection_count(), 1);

-        manager.broadcast(SseEvent::Thinking {
+        manager.broadcast(AppEvent::Thinking {
            message: "working".to_string(),
            thread_id: None,
        });

        let event = stream.next().await.unwrap();
        match event {
-            SseEvent::Thinking { message, .. } => assert_eq!(message, "working"),
+            AppEvent::Thinking { message, .. } => assert_eq!(message, "working"),
            _ => panic!("Expected Thinking event"),
        }
    }
@@ -329,12 +306,12 @@ mod tests {
        let mut s2 = Box::pin(manager.subscribe_raw(None).expect("should subscribe"));
        assert_eq!(manager.connection_count(), 2);

-        manager.broadcast(SseEvent::Heartbeat);
+        manager.broadcast(AppEvent::Heartbeat);

        let e1 = s1.next().await.unwrap();
        let e2 = s2.next().await.unwrap();
-        assert!(matches!(e1, SseEvent::Heartbeat));
-        assert!(matches!(e2, SseEvent::Heartbeat));
+        assert!(matches!(e1, AppEvent::Heartbeat));
+        assert!(matches!(e2, AppEvent::Heartbeat));

        drop(s1);
        assert_eq!(manager.connection_count(), 1);
@@ -373,25 +350,25 @@ mod tests {
        // Send event scoped to alice
        manager.broadcast_for_user(
            "alice",
-            SseEvent::Status {
+            AppEvent::Status {
                message: "alice only".to_string(),
                thread_id: None,
            },
        );

        // Send global event
-        manager.broadcast(SseEvent::Heartbeat);
+        manager.broadcast(AppEvent::Heartbeat);

        // Alice gets her scoped event
        let e = alice.next().await.unwrap();
-        assert!(matches!(e, SseEvent::Status { .. }));
+        assert!(matches!(e, AppEvent::Status { .. }));

        // Alice also gets the global heartbeat
        let e = alice.next().await.unwrap();
-        assert!(matches!(e, SseEvent::Heartbeat));
+        assert!(matches!(e, AppEvent::Heartbeat));

        // Bob only gets the global heartbeat (alice's event was filtered)
        let e = bob.next().await.unwrap(); // safety: test-only
-        assert!(matches!(e, SseEvent::Heartbeat)); // safety: test assertion
+        assert!(matches!(e, AppEvent::Heartbeat)); // safety: test assertion
    }
 }
@@ -186,6 +186,13 @@ function authenticate() {
      connectSSE();
      connectLogSSE();
      startGatewayStatusPolling();
+      // Hide the Users settings tab for non-admin users.
+      apiFetch('/api/profile').then(function(profile) {
+        if (profile && profile.role !== 'admin') {
+          var usersTab = document.querySelector('[data-settings-subtab="users"]');
+          if (usersTab) usersTab.style.display = 'none';
+        }
+      }).catch(function() {});
      checkTeeStatus();
      loadThreads();
      loadMemoryTree();
@@ -4265,9 +4272,9 @@ function renderRoutineDetail(routine) {
      + '<th>Trigger</th><th>Started</th><th>Completed</th><th>Status</th><th>Summary</th><th>Tokens</th>'
      + '</tr></thead><tbody>';
    for (const run of routine.recent_runs) {
-      const runStatusClass = run.status === 'Ok' ? 'completed'
-        : run.status === 'Failed' ? 'failed'
-        : run.status === 'Attention' ? 'stuck'
+      const runStatusClass = run.status === 'ok' ? 'completed'
+        : run.status === 'failed' ? 'failed'
+        : run.status === 'attention' ? 'stuck'
        : 'in_progress';
      html += '<tr>'
        + '<td>' + escapeHtml(run.trigger_type) + '</td>'
@@ -4339,6 +4346,165 @@ function formatRelativeTime(isoString) {
  return future ? I18n.t('time.daysFromNow', { n: days }) : I18n.t('time.daysAgo', { n: days });
 }

+// --- Users (admin) ---
+
+function loadUsers() {
+  apiFetch('/api/admin/users').then(function(data) {
+    renderUsersList(data.users || []);
+  }).catch(function(err) {
+    var tbody = document.getElementById('users-tbody');
+    var empty = document.getElementById('users-empty');
+    if (tbody) tbody.innerHTML = '';
+    if (empty) {
+      empty.style.display = 'block';
+      if (err.status === 403 || err.status === 401) {
+        empty.textContent = I18n.t('users.adminRequired');
+      } else {
+        empty.textContent = I18n.t('users.failedToLoad') + ': ' + err.message;
+      }
+    }
+  });
+}
+
+function renderUsersList(users) {
+  var tbody = document.getElementById('users-tbody');
+  var empty = document.getElementById('users-empty');
+  if (!users || users.length === 0) {
+    tbody.innerHTML = '';
+    empty.style.display = 'block';
+    empty.textContent = I18n.t('users.emptyState');
+    return;
+  }
+  empty.style.display = 'none';
+  tbody.innerHTML = users.map(function(u) {
+    var statusClass = u.status === 'active' ? 'active' : 'failed';
+    var roleLabel = u.role === 'admin' ? '<span class="badge badge-admin">' + I18n.t('users.roleAdmin') + '</span>' : '<span class="badge">' + I18n.t('users.roleMember') + '</span>';
+    var actions = '';
+    if (u.status === 'active') {
+      actions += '<button class="btn-small btn-danger" data-action="suspend-user" data-user-id="' + escapeHtml(u.id) + '">' + I18n.t('users.suspend') + '</button> ';
+    } else {
+      actions += '<button class="btn-small btn-primary" data-action="activate-user" data-user-id="' + escapeHtml(u.id) + '">' + I18n.t('users.activate') + '</button> ';
+    }
+    if (u.role === 'member') {
+      actions += '<button class="btn-small" data-action="change-role" data-user-id="' + escapeHtml(u.id) + '" data-role="admin">' + I18n.t('users.makeAdmin') + '</button> ';
+    } else {
+      actions += '<button class="btn-small" data-action="change-role" data-user-id="' + escapeHtml(u.id) + '" data-role="member">' + I18n.t('users.makeMember') + '</button> ';
+    }
+    actions += '<button class="btn-small" data-action="create-token" data-user-id="' + escapeHtml(u.id) + '" data-user-name="' + escapeHtml(u.display_name) + '">' + I18n.t('users.addToken') + '</button>';
+    return '<tr>'
+      + '<td class="user-id" title="' + escapeHtml(u.id) + '">' + escapeHtml(u.id.substring(0, 8)) + '…</td>'
+      + '<td>' + escapeHtml(u.display_name) + '</td>'
+      + '<td>' + escapeHtml(u.email || '—') + '</td>'
+      + '<td>' + roleLabel + '</td>'
+      + '<td><span class="status-badge ' + statusClass + '">' + escapeHtml(u.status) + '</span></td>'
+      + '<td>' + (u.job_count || 0) + '</td>'
+      + '<td>' + formatCost(u.total_cost) + '</td>'
+      + '<td>' + (u.last_active_at ? formatRelativeTime(u.last_active_at) : '—') + '</td>'
+      + '<td>' + formatRelativeTime(u.created_at) + '</td>'
+      + '<td>' + actions + '</td>'
+      + '</tr>';
+  }).join('');
+}
+
+function suspendUser(userId) {
+  apiFetch('/api/admin/users/' + userId + '/suspend', { method: 'POST' })
+    .then(function() { loadUsers(); })
+    .catch(function(e) { alert(I18n.t('users.failedSuspend') + ': ' + e.message); });
+}
+
+function activateUser(userId) {
+  apiFetch('/api/admin/users/' + userId + '/activate', { method: 'POST' })
+    .then(function() { loadUsers(); })
+    .catch(function(e) { alert(I18n.t('users.failedActivate') + ': ' + e.message); });
+}
+
+function changeUserRole(userId, newRole) {
+  apiFetch('/api/admin/users/' + userId, {
+    method: 'PATCH',
+    headers: { 'Content-Type': 'application/json' },
+    body: JSON.stringify({ role: newRole })
+  })
+    .then(function() { loadUsers(); })
+    .catch(function(e) { alert(I18n.t('users.failedRoleChange') + ': ' + e.message); });
+}
+
+function createTokenForUser(userId, displayName) {
+  var tokenName = prompt('Token name for ' + displayName + ':', 'api-token');
+  if (!tokenName) return;
+  apiFetch('/api/tokens', {
+    method: 'POST',
+    headers: { 'Content-Type': 'application/json' },
+    body: JSON.stringify({ name: tokenName, user_id: userId }),
+  }).then(function(data) {
+    showTokenBanner(data.token, I18n.t('users.tokenCreated'));
+  }).catch(function(e) { alert(I18n.t('users.failedCreate') + ': ' + e.message); });
+}
+
+function showTokenBanner(tokenValue, title) {
+  var banner = document.getElementById('users-token-result');
+  if (!banner) return;
+  var heading = title || I18n.t('users.tokenCreated');
+  var loginUrl = window.location.origin + '/?token=' + encodeURIComponent(tokenValue);
+  banner.style.display = 'block';
+  banner.innerHTML = '<strong>' + escapeHtml(heading) + '</strong> ' + I18n.t('users.tokenShareMessage') + '<br>'
+    + '<code class="token-display" id="token-copy-value">' + escapeHtml(loginUrl) + '</code>'
+    + '<button class="btn-small" id="token-copy-link">Copy Link</button>'
+    + '<br><span style="font-size:0.8em;color:var(--text-muted)">' + I18n.t('users.rawToken') + ' ' + escapeHtml(tokenValue) + '</span>';
+  document.getElementById('token-copy-link').addEventListener('click', function() {
+    navigator.clipboard.writeText(loginUrl);
+    this.textContent = I18n.t('users.copied');
+  });
+}
+
+// Delegated click handler for user action buttons (CSP-safe, no inline onclick)
+document.getElementById('users-table')?.addEventListener('click', function(e) {
+  var btn = e.target.closest('[data-action]');
+  if (!btn) return;
+  var action = btn.getAttribute('data-action');
+  var userId = btn.getAttribute('data-user-id');
+  var userName = btn.getAttribute('data-user-name');
+  if (action === 'suspend-user') suspendUser(userId);
+  else if (action === 'activate-user') activateUser(userId);
+  else if (action === 'change-role') changeUserRole(userId, btn.getAttribute('data-role'));
+  else if (action === 'create-token') createTokenForUser(userId, userName || '');
+});
+
+// Wire up Users tab create form
+document.getElementById('users-create-btn')?.addEventListener('click', function() {
+  document.getElementById('users-create-form').style.display = 'flex';
+  document.getElementById('users-token-result').style.display = 'none';
+  document.getElementById('user-display-name').focus();
+});
+
+document.getElementById('users-create-cancel')?.addEventListener('click', function() {
+  document.getElementById('users-create-form').style.display = 'none';
+});
+
+document.getElementById('users-create-submit')?.addEventListener('click', function() {
+  var displayName = document.getElementById('user-display-name').value.trim();
+  var email = document.getElementById('user-email').value.trim();
+  var role = document.getElementById('user-role').value;
+  if (!displayName) { alert(I18n.t('users.displayNameRequired')); return; }
+
+  apiFetch('/api/admin/users', {
+    method: 'POST',
+    headers: { 'Content-Type': 'application/json' },
+    body: JSON.stringify({
+      display_name: displayName,
+      email: email || undefined,
+      role: role,
+    }),
+  }).then(function(data) {
+    document.getElementById('users-create-form').style.display = 'none';
+    document.getElementById('user-display-name').value = '';
+    document.getElementById('user-email').value = '';
+    if (data.token) {
+      showTokenBanner(data.token, I18n.t('users.userCreated'));
+    }
+    loadUsers();
+  }).catch(function(e) { alert(I18n.t('users.failedCreate') + ': ' + e.message); });
+});
+
 // --- Gateway status widget ---

 let gatewayStatusInterval = null;
@@ -5028,6 +5194,7 @@ function loadSettingsSubtab(subtab) {
  else if (subtab === 'extensions') { loadExtensions(); startPairingPoll(); }
  else if (subtab === 'mcp') loadMcpServers();
  else if (subtab === 'skills') loadSkills();
+  else if (subtab === 'users') loadUsers();
  if (subtab !== 'extensions' && subtab !== 'channels') stopPairingPoll();
 }

@@ -9,8 +9,6 @@ I18n.register('en', {
  'auth.connect': 'Connect',
  'auth.errorRequired': 'Token required',
  'auth.errorInvalid': 'Invalid token',
-  'auth.hint': 'Enter the GATEWAY_AUTH_TOKEN from your .env file',
-  
  // Chat
  'chat.inputPlaceholder': 'Message or / for commands...',
  
@@ -44,7 +42,46 @@ I18n.register('en', {
  'settings.channels': 'Channels',
  'settings.networking': 'Networking',
  'settings.mcp': 'MCP',
-  
+  'settings.users': 'Users',
+
+  // Users Tab
+  'users.heading': 'User Management',
+  'users.newUser': '+ New User',
+  'users.displayNamePlaceholder': 'Display name',
+  'users.emailPlaceholder': 'Email (optional)',
+  'users.roleMember': 'Member',
+  'users.roleAdmin': 'Admin',
+  'users.create': 'Create',
+  'users.cancel': 'Cancel',
+  'users.emptyState': 'No users found. Create the first user to get started.',
+  'users.adminRequired': 'Admin access required to manage users.',
+  'users.failedToLoad': 'Failed to load users',
+  'users.suspend': 'Suspend',
+  'users.activate': 'Activate',
+  'users.addToken': '+ Token',
+  'users.failedSuspend': 'Failed to suspend user',
+  'users.failedActivate': 'Failed to activate user',
+  'users.makeAdmin': 'Make Admin',
+  'users.makeMember': 'Make Member',
+  'users.failedRoleChange': 'Failed to change role',
+  'users.userCreated': 'User created!',
+  'users.tokenCreated': 'Token created!',
+  'users.tokenShareMessage': "Share this login link — it won't be shown again:",
+  'users.rawToken': 'Raw token:',
+  'users.copied': 'Copied!',
+  'users.displayNameRequired': 'Display name is required',
+  'users.failedCreate': 'Failed to create user',
+  'users.columns.id': 'ID',
+  'users.columns.displayName': 'Display Name',
+  'users.columns.email': 'Email',
+  'users.columns.role': 'Role',
+  'users.columns.status': 'Status',
+  'users.columns.jobs': 'Jobs',
+  'users.columns.cost': 'Cost',
+  'users.columns.lastActive': 'Last Active',
+  'users.columns.created': 'Created',
+  'users.columns.actions': 'Actions',
+
  // Status
  'status.connected': 'Connected',
  'status.disconnected': 'Disconnected',
@@ -9,8 +9,6 @@ I18n.register('zh-CN', {
  'auth.connect': '连接',
  'auth.errorRequired': '请输入令牌',
  'auth.errorInvalid': '令牌无效',
-  'auth.hint': '输入 .env 配置文件中的 GATEWAY_AUTH_TOKEN',
-  
  // 聊天
  'chat.inputPlaceholder': '输入消息或 / 以使用命令...',
  
@@ -44,7 +42,46 @@ I18n.register('zh-CN', {
  'settings.channels': '频道',
  'settings.networking': '网络',
  'settings.mcp': 'MCP',
-  
+  'settings.users': '用户管理',
+
+  // 用户管理标签页
+  'users.heading': '用户管理',
+  'users.newUser': '+ 新用户',
+  'users.displayNamePlaceholder': '显示名称',
+  'users.emailPlaceholder': '邮箱（可选）',
+  'users.roleMember': '成员',
+  'users.roleAdmin': '管理员',
+  'users.create': '创建',
+  'users.cancel': '取消',
+  'users.emptyState': '暂无用户。创建第一个用户以开始使用。',
+  'users.adminRequired': '需要管理员权限来管理用户。',
+  'users.failedToLoad': '加载用户列表失败',
+  'users.suspend': '停用',
+  'users.activate': '启用',
+  'users.addToken': '+ 令牌',
+  'users.failedSuspend': '停用用户失败',
+  'users.failedActivate': '启用用户失败',
+  'users.makeAdmin': '设为管理员',
+  'users.makeMember': '设为成员',
+  'users.failedRoleChange': '更改角色失败',
+  'users.userCreated': '用户已创建！',
+  'users.tokenCreated': '令牌已创建！',
+  'users.tokenShareMessage': '分享此登录链接——此链接只会显示一次：',
+  'users.rawToken': '原始令牌：',
+  'users.copied': '已复制！',
+  'users.displayNameRequired': '显示名称为必填项',
+  'users.failedCreate': '创建用户失败',
+  'users.columns.id': 'ID',
+  'users.columns.displayName': '显示名称',
+  'users.columns.email': '邮箱',
+  'users.columns.role': '角色',
+  'users.columns.status': '状态',
+  'users.columns.jobs': '任务',
+  'users.columns.cost': '费用',
+  'users.columns.lastActive': '最近活跃',
+  'users.columns.created': '创建时间',
+  'users.columns.actions': '操作',
+
  // 状态
  'status.connected': '已连接',
  'status.disconnected': '已断开',
@@ -41,7 +41,6 @@
        <button id="auth-connect-btn" data-i18n="auth.connect">Connect</button>
      </div>
      <div id="auth-error"></div>
-      <p class="auth-hint" data-i18n="auth.hint">Enter the GATEWAY_AUTH_TOKEN from your .env configuration.</p>
    </div>
  </div>

@@ -293,6 +292,7 @@
          <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>
+          <button class="settings-subtab" data-settings-subtab="users" data-i18n="settings.users">Users</button>
          <button class="settings-theme-toggle" id="settings-theme-toggle" data-i18n="theme.tooltipSystem" title="Toggle theme">Theme</button>
        </div>
        <div class="settings-content">
@@ -390,6 +390,29 @@
              </div>
            </div>
          </div>
+          <div class="settings-subpanel" id="settings-users">
+            <div class="users-container">
+              <div class="users-header">
+                <h3 data-i18n="users.heading">User Management</h3>
+                <button id="users-create-btn" class="btn-primary" data-i18n="users.newUser">+ New User</button>
+              </div>
+              <div id="users-create-form" style="display:none" class="users-form" autocomplete="off">
+                <input type="text" id="user-display-name" data-i18n-placeholder="users.displayNamePlaceholder" placeholder="Display name" autocomplete="off" />
+                <input type="text" id="user-email" data-i18n-placeholder="users.emailPlaceholder" placeholder="Email (optional)" autocomplete="off" />
+                <select id="user-role"><option value="member" data-i18n="users.roleMember">Member</option><option value="admin" data-i18n="users.roleAdmin">Admin</option></select>
+                <button id="users-create-submit" class="btn-primary" data-i18n="users.create">Create</button>
+                <button id="users-create-cancel" class="btn-secondary" data-i18n="users.cancel">Cancel</button>
+              </div>
+              <div id="users-token-result" style="display:none" class="users-token-banner"></div>
+              <table class="routines-table" id="users-table">
+                <thead><tr>
+                  <th data-i18n="users.columns.id">ID</th><th data-i18n="users.columns.displayName">Display Name</th><th data-i18n="users.columns.email">Email</th><th data-i18n="users.columns.role">Role</th><th data-i18n="users.columns.status">Status</th><th data-i18n="users.columns.jobs">Jobs</th><th data-i18n="users.columns.cost">Cost</th><th data-i18n="users.columns.lastActive">Last Active</th><th data-i18n="users.columns.created">Created</th><th data-i18n="users.columns.actions">Actions</th>
+                </tr></thead>
+                <tbody id="users-tbody"></tbody>
+              </table>
+              <div id="users-empty" class="empty-state" style="display:none" data-i18n="users.emptyState">No users found. Create the first user to get started.</div>
+            </div>
+          </div>
        </div>
      </div>
    </div>
@@ -5429,3 +5429,22 @@ body.theme-transition *:not(svg):not(path):not(line):not(circle):not(rect) {
    --text-muted: #a1a1aa;
  }
 }
+
+/* --- Users Tab --- */
+.users-container { padding: 1rem; }
+.users-header { display: flex; align-items: center; justify-content: space-between; margin-bottom: 1rem; }
+.users-header h3 { margin: 0; font-size: 1.1rem; }
+.users-form { display: flex; gap: 0.5rem; align-items: center; margin-bottom: 1rem; flex-wrap: wrap; }
+.users-form input, .users-form select { padding: 0.4rem 0.6rem; border-radius: 6px; border: 1px solid var(--border); background: var(--bg-secondary); color: var(--text-primary); font-size: 0.85rem; }
+.users-token-banner { background: var(--bg-tertiary); border: 1px solid var(--accent); border-radius: 8px; padding: 0.75rem 1rem; margin-bottom: 1rem; font-size: 0.85rem; }
+.token-display { display: inline-block; padding: 0.3rem 0.6rem; background: var(--bg-primary); border-radius: 4px; font-family: var(--font-mono); word-break: break-all; margin: 0.4rem 0; user-select: all; }
+.user-id { font-family: var(--font-mono); font-size: 0.8rem; color: var(--text-muted); }
+.badge { display: inline-block; padding: 0.15rem 0.5rem; border-radius: 10px; font-size: 0.75rem; background: var(--bg-tertiary); color: var(--text-secondary); }
+.badge-admin { background: var(--accent); color: #fff; }
+.btn-small { padding: 0.25rem 0.5rem; font-size: 0.75rem; border-radius: 4px; border: 1px solid var(--border); background: var(--bg-secondary); color: var(--text-primary); cursor: pointer; }
+.btn-small:hover { background: var(--bg-tertiary); }
+.btn-danger { border-color: #ef4444; color: #ef4444; }
+.btn-danger:hover { background: #ef4444; color: #fff; }
+.btn-primary { background: var(--accent); color: #fff; border: none; padding: 0.4rem 0.8rem; border-radius: 6px; cursor: pointer; font-size: 0.85rem; }
+.btn-primary:hover { opacity: 0.9; }
+.btn-secondary { background: var(--bg-tertiary); color: var(--text-primary); border: 1px solid var(--border); padding: 0.4rem 0.8rem; border-radius: 6px; cursor: pointer; font-size: 0.85rem; }
@@ -76,7 +76,7 @@ impl TestGatewayBuilder {
            store: None,
            job_manager: None,
            prompt_queue: None,
-            default_user_id: self.user_id,
+            owner_id: self.user_id.clone(),
            shutdown_tx: tokio::sync::RwLock::new(None),
            ws_tracker: Some(Arc::new(WsConnectionTracker::new())),
            llm_provider: self.llm_provider,
@@ -91,6 +91,8 @@ impl TestGatewayBuilder {
            routine_engine: Arc::new(tokio::sync::RwLock::new(None)),
            startup_time: std::time::Instant::now(),
            active_config: crate::channels::web::server::ActiveConfigSnapshot::default(),
+            secrets_store: None,
+            db_auth: None,
        })
    }

@@ -105,7 +107,7 @@ impl TestGatewayBuilder {
        let addr: SocketAddr = "127.0.0.1:0"
            .parse()
            .expect("hard-coded address must parse"); // safety: constant literal
-        let bound = start_server(addr, state.clone(), auth).await?;
+        let bound = start_server(addr, state.clone(), auth.into()).await?;
        Ok((bound, state))
    }

@@ -119,7 +121,7 @@ impl TestGatewayBuilder {
        let addr: SocketAddr = "127.0.0.1:0"
            .parse()
            .expect("hard-coded address must parse"); // safety: constant literal
-        let bound = start_server(addr, state.clone(), auth).await?;
+        let bound = start_server(addr, state.clone(), auth.into()).await?;
        Ok((bound, state))
    }
 }
@@ -33,6 +33,7 @@ fn two_user_auth() -> MultiAuthState {
        "tok-alice".to_string(),
        UserIdentity {
            user_id: "alice".to_string(),
+            role: "admin".to_string(),
            workspace_read_scopes: vec!["shared".to_string()],
        },
    );
@@ -40,6 +41,7 @@ fn two_user_auth() -> MultiAuthState {
        "tok-bob".to_string(),
        UserIdentity {
            user_id: "bob".to_string(),
+            role: "admin".to_string(),
            workspace_read_scopes: vec!["shared".to_string(), "alice".to_string()],
        },
    );
@@ -64,7 +66,7 @@ fn build_state(
        store,
        job_manager: None,
        prompt_queue,
-        default_user_id: "test".to_string(),
+        owner_id: "test".to_string(),
        shutdown_tx: tokio::sync::RwLock::new(None),
        ws_tracker: None,
        llm_provider: None,
@@ -79,6 +81,8 @@ fn build_state(
        routine_engine: Arc::new(tokio::sync::RwLock::new(None)),
        startup_time: std::time::Instant::now(),
        active_config: ActiveConfigSnapshot::default(),
+        secrets_store: None,
+        db_auth: None,
    })
 }

@@ -188,6 +192,7 @@ mod workspace_pool {
        );
        let identity = UserIdentity {
            user_id: "alice".to_string(),
+            role: "admin".to_string(),
            workspace_read_scopes: vec![],
        };
        let ws = pool.get_or_create(&identity).await;
@@ -216,6 +221,7 @@ mod workspace_pool {
        );
        let identity = UserIdentity {
            user_id: "alice".to_string(),
+            role: "admin".to_string(),
            workspace_read_scopes: vec![],
        };
        let ws = pool.get_or_create(&identity).await;
@@ -239,6 +245,7 @@ mod workspace_pool {
        );
        let identity = UserIdentity {
            user_id: "bob".to_string(),
+            role: "admin".to_string(),
            workspace_read_scopes: vec!["alice".to_string(), "shared".to_string()],
        };
        let ws = pool.get_or_create(&identity).await;
@@ -265,10 +272,12 @@ mod workspace_pool {
        );
        let alice_id = UserIdentity {
            user_id: "alice".to_string(),
+            role: "admin".to_string(),
            workspace_read_scopes: vec![],
        };
        let bob_id = UserIdentity {
            user_id: "bob".to_string(),
+            role: "admin".to_string(),
            workspace_read_scopes: vec![],
        };

@@ -300,6 +309,7 @@ mod workspace_pool {
        );
        let identity = UserIdentity {
            user_id: "alice".to_string(),
+            role: "admin".to_string(),
            workspace_read_scopes: vec!["token-scope".to_string()],
        };
        let ws = pool.get_or_create(&identity).await;
@@ -340,7 +350,10 @@ mod jobs_isolation {
            .route("/api/jobs/{id}/cancel", post(jobs_cancel_handler))
            .route("/api/jobs/{id}/restart", post(jobs_restart_handler))
            .route("/api/jobs/{id}/prompt", post(jobs_prompt_handler))
-            .layer(middleware::from_fn_with_state(auth, auth_middleware))
+            .layer(middleware::from_fn_with_state(
+                crate::channels::web::auth::CombinedAuthState::from(auth),
+                auth_middleware,
+            ))
            .with_state(state)
    }

@@ -546,7 +559,10 @@ mod routines_isolation {
            .route("/api/routines/{id}", get(routines_detail_handler))
            .route("/api/routines/{id}/toggle", post(routines_toggle_handler))
            .route("/api/routines/{id}", delete(routines_delete_handler))
-            .layer(middleware::from_fn_with_state(auth, auth_middleware))
+            .layer(middleware::from_fn_with_state(
+                crate::channels::web::auth::CombinedAuthState::from(auth),
+                auth_middleware,
+            ))
            .with_state(state)
    }

@@ -671,7 +687,10 @@ mod auth_enforcement {
            .route("/api/logs/level", get(authed_handler).put(authed_handler))
            // Gateway status
            .route("/api/gateway/status", get(authed_handler))
-            .layer(middleware::from_fn_with_state(auth, auth_middleware))
+            .layer(middleware::from_fn_with_state(
+                crate::channels::web::auth::CombinedAuthState::from(auth),
+                auth_middleware,
+            ))
            .with_state(state)
    }

@@ -794,3 +813,140 @@ mod auth_enforcement {
        assert_eq!(resp.status(), StatusCode::UNAUTHORIZED);
    }
 }
+
+// ═══════════════════════════════════════════════════════════════════════
+// Admin Endpoint Role Enforcement Tests
+// ═══════════════════════════════════════════════════════════════════════
+
+mod admin_role_enforcement {
+    use super::*;
+    use crate::channels::web::handlers::users::{
+        users_activate_handler, users_detail_handler, users_list_handler, users_suspend_handler,
+        users_update_handler,
+    };
+    use axum::routing::patch;
+
+    /// Build a router with admin user endpoints behind multi-user auth.
+    /// Uses a member-role token and an admin-role token.
+    fn admin_router() -> Router {
+        let mut tokens = HashMap::new();
+        tokens.insert(
+            "tok-admin".to_string(),
+            UserIdentity {
+                user_id: "admin-user".to_string(),
+                role: "admin".to_string(),
+                workspace_read_scopes: vec![],
+            },
+        );
+        tokens.insert(
+            "tok-member".to_string(),
+            UserIdentity {
+                user_id: "member-user".to_string(),
+                role: "member".to_string(),
+                workspace_read_scopes: vec![],
+            },
+        );
+        let auth = MultiAuthState::multi(tokens);
+        let state = build_state(None, None);
+
+        Router::new()
+            .route("/api/admin/users", get(users_list_handler))
+            .route("/api/admin/users/{id}", get(users_detail_handler))
+            .route("/api/admin/users/{id}", patch(users_update_handler))
+            .route("/api/admin/users/{id}/suspend", post(users_suspend_handler))
+            .route(
+                "/api/admin/users/{id}/activate",
+                post(users_activate_handler),
+            )
+            .layer(middleware::from_fn_with_state(
+                crate::channels::web::auth::CombinedAuthState::from(auth),
+                auth_middleware,
+            ))
+            .with_state(state)
+    }
+
+    /// Assert a request returns FORBIDDEN for a member token.
+    async fn assert_forbidden_for_member(app: &Router, method: Method, uri: &str) {
+        let req = Request::builder()
+            .method(method)
+            .uri(uri)
+            .header("Authorization", "Bearer tok-member")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.clone().oneshot(req).await.unwrap();
+        assert_eq!(
+            resp.status(),
+            StatusCode::FORBIDDEN,
+            "expected 403 for member on {}",
+            uri
+        );
+    }
+
+    #[tokio::test]
+    async fn test_admin_user_endpoints_reject_member_role() {
+        let app = admin_router();
+
+        assert_forbidden_for_member(&app, Method::GET, "/api/admin/users").await;
+        assert_forbidden_for_member(&app, Method::GET, "/api/admin/users/some-id").await;
+        assert_forbidden_for_member(&app, Method::POST, "/api/admin/users/some-id/suspend").await;
+        assert_forbidden_for_member(&app, Method::POST, "/api/admin/users/some-id/activate").await;
+    }
+
+    #[tokio::test]
+    async fn test_admin_user_endpoints_accept_admin_role() {
+        let app = admin_router();
+
+        // Admin token should pass auth (will get 503 since no DB, but not 403).
+        let req = Request::builder()
+            .uri("/api/admin/users")
+            .header("Authorization", "Bearer tok-admin")
+            .body(Body::empty())
+            .unwrap();
+        let resp = app.clone().oneshot(req).await.unwrap();
+        assert_ne!(
+            resp.status(),
+            StatusCode::FORBIDDEN,
+            "admin should not get 403"
+        );
+    }
+}
+
+// ═══════════════════════════════════════════════════════════════════════
+// DbAuthenticator Cache Bounded Tests
+// ═══════════════════════════════════════════════════════════════════════
+
+mod db_auth_cache {
+    use super::*;
+    use std::time::Instant;
+
+    #[tokio::test]
+    async fn test_cache_bounded_by_max_entries() {
+        // Access the internal cache and verify LRU eviction.
+        // We can't easily test through `authenticate()` since it hits the DB,
+        // so we test the LRU cache directly.
+        let cap = std::num::NonZeroUsize::new(4).unwrap(); // safety: test-only, 4 is non-zero
+        let cache: lru::LruCache<[u8; 32], (UserIdentity, Instant)> = lru::LruCache::new(cap);
+        let cache = Arc::new(tokio::sync::RwLock::new(cache));
+
+        {
+            let mut c = cache.write().await;
+            for i in 0..10u8 {
+                let mut hash = [0u8; 32];
+                hash[0] = i;
+                c.put(
+                    hash,
+                    (
+                        UserIdentity {
+                            user_id: format!("user-{i}"),
+                            role: "member".to_string(),
+                            workspace_read_scopes: vec![],
+                        },
+                        Instant::now(),
+                    ),
+                );
+            }
+            // Cache must be bounded at capacity, not grown to 10.
+            assert_eq!(c.len(), 4, "cache should be bounded to capacity"); // safety: test assertion
+        }
+    }
+}
@@ -63,6 +63,9 @@ pub struct TurnInfo {
    pub started_at: String,
    pub completed_at: Option<String>,
    pub tool_calls: Vec<ToolCallInfo>,
+    /// Agent's reasoning narrative for this turn.
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub narrative: Option<String>,
 }

 #[derive(Debug, Serialize)]
@@ -74,6 +77,9 @@ pub struct ToolCallInfo {
    pub result_preview: Option<String>,
    #[serde(skip_serializing_if = "Option::is_none")]
    pub error: Option<String>,
+    /// Agent's reasoning for choosing this tool.
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub rationale: Option<String>,
 }

 #[derive(Debug, Serialize)]
@@ -114,165 +120,9 @@ pub struct ApprovalRequest {
    pub thread_id: Option<String>,
 }

-// --- SSE Event Types ---
+// --- App Event (re-exported from ironclaw_common) ---

-#[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>,
-    },
-
-    /// Per-turn token usage and cost summary.
-    #[serde(rename = "turn_cost")]
-    TurnCost {
-        input_tokens: u64,
-        output_tokens: u64,
-        cost_usd: 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>,
-    },
-}
+pub use ironclaw_common::{AppEvent, ToolDecisionDto};

 // --- Memory ---

@@ -784,32 +634,9 @@ pub enum WsServerMessage {
 }

 impl WsServerMessage {
-    /// Create a WsServerMessage from an SseEvent.
-    pub fn from_sse_event(event: &SseEvent) -> Self {
-        let event_type = match event {
-            SseEvent::Response { .. } => "response",
-            SseEvent::Thinking { .. } => "thinking",
-            SseEvent::ToolStarted { .. } => "tool_started",
-            SseEvent::ToolCompleted { .. } => "tool_completed",
-            SseEvent::ToolResult { .. } => "tool_result",
-            SseEvent::StreamChunk { .. } => "stream_chunk",
-            SseEvent::Status { .. } => "status",
-            SseEvent::JobStarted { .. } => "job_started",
-            SseEvent::ApprovalNeeded { .. } => "approval_needed",
-            SseEvent::AuthRequired { .. } => "auth_required",
-            SseEvent::AuthCompleted { .. } => "auth_completed",
-            SseEvent::Error { .. } => "error",
-            SseEvent::Heartbeat => "heartbeat",
-            SseEvent::JobMessage { .. } => "job_message",
-            SseEvent::JobToolUse { .. } => "job_tool_use",
-            SseEvent::JobToolResult { .. } => "job_tool_result",
-            SseEvent::JobStatus { .. } => "job_status",
-            SseEvent::JobResult { .. } => "job_result",
-            SseEvent::ImageGenerated { .. } => "image_generated",
-            SseEvent::Suggestions { .. } => "suggestions",
-            SseEvent::TurnCost { .. } => "turn_cost",
-            SseEvent::ExtensionStatus { .. } => "extension_status",
-        };
+    /// Create a WsServerMessage from an AppEvent.
+    pub fn from_app_event(event: &AppEvent) -> Self {
+        let event_type = event.event_type();
        let data = serde_json::to_value(event).unwrap_or(serde_json::Value::Null);
        WsServerMessage::Event {
            event_type: event_type.to_string(),
@@ -1101,12 +928,12 @@ mod tests {
    }

    #[test]
-    fn test_ws_server_from_sse_response() {
-        let sse = SseEvent::Response {
+    fn test_ws_server_from_app_event_response() {
+        let event = AppEvent::Response {
            content: "hello".to_string(),
            thread_id: "t1".to_string(),
        };
-        let ws = WsServerMessage::from_sse_event(&sse);
+        let ws = WsServerMessage::from_app_event(&event);
        match ws {
            WsServerMessage::Event { event_type, data } => {
                assert_eq!(event_type, "response");
@@ -1118,12 +945,12 @@ mod tests {
    }

    #[test]
-    fn test_ws_server_from_sse_thinking() {
-        let sse = SseEvent::Thinking {
+    fn test_ws_server_from_app_event_thinking() {
+        let event = AppEvent::Thinking {
            message: "reasoning...".to_string(),
            thread_id: None,
        };
-        let ws = WsServerMessage::from_sse_event(&sse);
+        let ws = WsServerMessage::from_app_event(&event);
        match ws {
            WsServerMessage::Event { event_type, data } => {
                assert_eq!(event_type, "thinking");
@@ -1134,8 +961,8 @@ mod tests {
    }

    #[test]
-    fn test_ws_server_from_sse_approval_needed() {
-        let sse = SseEvent::ApprovalNeeded {
+    fn test_ws_server_from_app_event_approval_needed() {
+        let event = AppEvent::ApprovalNeeded {
            request_id: "r1".to_string(),
            tool_name: "shell".to_string(),
            description: "Run ls".to_string(),
@@ -1143,7 +970,7 @@ mod tests {
            thread_id: Some("t1".to_string()),
            allow_always: true,
        };
-        let ws = WsServerMessage::from_sse_event(&sse);
+        let ws = WsServerMessage::from_app_event(&event);
        match ws {
            WsServerMessage::Event { event_type, data } => {
                assert_eq!(event_type, "approval_needed");
@@ -1155,9 +982,9 @@ mod tests {
    }

    #[test]
-    fn test_ws_server_from_sse_heartbeat() {
-        let sse = SseEvent::Heartbeat;
-        let ws = WsServerMessage::from_sse_event(&sse);
+    fn test_ws_server_from_app_event_heartbeat() {
+        let event = AppEvent::Heartbeat;
+        let ws = WsServerMessage::from_app_event(&event);
        match ws {
            WsServerMessage::Event { event_type, .. } => {
                assert_eq!(event_type, "heartbeat");
@@ -1197,8 +1024,8 @@ mod tests {
    }

    #[test]
-    fn test_sse_auth_required_serialize() {
-        let event = SseEvent::AuthRequired {
+    fn test_app_event_auth_required_serialize() {
+        let event = AppEvent::AuthRequired {
            extension_name: "notion".to_string(),
            instructions: Some("Get your token from...".to_string()),
            auth_url: None,
@@ -1214,8 +1041,8 @@ mod tests {
    }

    #[test]
-    fn test_sse_auth_completed_serialize() {
-        let event = SseEvent::AuthCompleted {
+    fn test_app_event_auth_completed_serialize() {
+        let event = AppEvent::AuthCompleted {
            extension_name: "notion".to_string(),
            success: true,
            message: "notion authenticated (3 tools loaded)".to_string(),
@@ -1228,14 +1055,14 @@ mod tests {
    }

    #[test]
-    fn test_ws_server_from_sse_auth_required() {
-        let sse = SseEvent::AuthRequired {
+    fn test_ws_server_from_app_event_auth_required() {
+        let event = AppEvent::AuthRequired {
            extension_name: "openai".to_string(),
            instructions: Some("Enter API key".to_string()),
            auth_url: None,
            setup_url: None,
        };
-        let ws = WsServerMessage::from_sse_event(&sse);
+        let ws = WsServerMessage::from_app_event(&event);
        match ws {
            WsServerMessage::Event { event_type, data } => {
                assert_eq!(event_type, "auth_required");
@@ -1246,13 +1073,13 @@ mod tests {
    }

    #[test]
-    fn test_ws_server_from_sse_auth_completed() {
-        let sse = SseEvent::AuthCompleted {
+    fn test_ws_server_from_app_event_auth_completed() {
+        let event = AppEvent::AuthCompleted {
            extension_name: "slack".to_string(),
            success: false,
            message: "Invalid token".to_string(),
        };
-        let ws = WsServerMessage::from_sse_event(&sse);
+        let ws = WsServerMessage::from_app_event(&event);
        match ws {
            WsServerMessage::Event { event_type, data } => {
                assert_eq!(event_type, "auth_completed");
@@ -2,28 +2,26 @@

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

-/// 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 {
-    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]);
+pub use ironclaw_common::truncate_preview;

-    // 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>");
-    }
+/// Convert stored tool errors into plain text suitable for UI display.
+pub fn tool_error_for_display(error: &str) -> String {
+    ironclaw_safety::SafetyLayer::unwrap_tool_output(error).unwrap_or_else(|| error.to_string())
+}

-    result
+/// Parse tool call summary JSON objects into `ToolCallInfo` structs.
+fn parse_tool_call_infos(calls: &[serde_json::Value]) -> Vec<ToolCallInfo> {
+    calls
+        .iter()
+        .map(|c| ToolCallInfo {
+            name: c["name"].as_str().unwrap_or("unknown").to_string(),
+            has_result: c.get("result_preview").is_some_and(|v| !v.is_null()),
+            has_error: c.get("error").is_some_and(|v| !v.is_null()),
+            result_preview: c["result_preview"].as_str().map(String::from),
+            error: c["error"].as_str().map(tool_error_for_display),
+            rationale: c["rationale"].as_str().map(String::from),
+        })
+        .collect()
 }

 /// Build TurnInfo pairs from flat DB messages (user/tool_calls/assistant triples).
@@ -49,6 +47,7 @@ pub fn build_turns_from_db_messages(
                started_at: msg.created_at.to_rfc3339(),
                completed_at: None,
                tool_calls: Vec::new(),
+                narrative: None,
            };

            // Check if next message is a tool_calls record
@@ -56,18 +55,28 @@ pub fn build_turns_from_db_messages(
                && next.role == "tool_calls"
            {
                let tc_msg = iter.next().expect("peeked");
-                match serde_json::from_str::<Vec<serde_json::Value>>(&tc_msg.content) {
-                    Ok(calls) => {
-                        turn.tool_calls = calls
-                            .iter()
-                            .map(|c| ToolCallInfo {
-                                name: c["name"].as_str().unwrap_or("unknown").to_string(),
-                                has_result: c.get("result_preview").is_some(),
-                                has_error: c.get("error").is_some(),
-                                result_preview: c["result_preview"].as_str().map(String::from),
-                                error: c["error"].as_str().map(String::from),
-                            })
-                            .collect();
+                // Parse tool_calls JSON — supports two formats:
+                // safety: no byte-index slicing; comment describes JSON shape
+                match serde_json::from_str::<serde_json::Value>(&tc_msg.content) {
+                    Ok(serde_json::Value::Array(calls)) => {
+                        // Old format: plain array
+                        turn.tool_calls = parse_tool_call_infos(&calls);
+                    }
+                    Ok(serde_json::Value::Object(obj)) => {
+                        // New wrapped format with narrative
+                        turn.narrative = obj
+                            .get("narrative")
+                            .and_then(|v| v.as_str())
+                            .map(String::from);
+                        if let Some(serde_json::Value::Array(calls)) = obj.get("calls") {
+                            turn.tool_calls = parse_tool_call_infos(calls);
+                        }
+                    }
+                    Ok(_) => {
+                        tracing::warn!(
+                            message_id = %tc_msg.id,
+                            "Unexpected tool_calls JSON shape in DB, skipping"
+                        );
                    }
                    Err(e) => {
                        tracing::warn!(
@@ -105,6 +114,7 @@ pub fn build_turns_from_db_messages(
                started_at: msg.created_at.to_rfc3339(),
                completed_at: Some(msg.created_at.to_rfc3339()),
                tool_calls: Vec::new(),
+                narrative: None,
            });
            turn_number += 1;
        }
@@ -118,88 +128,6 @@ mod tests {
    use super::*;
    use uuid::Uuid;

-    // ---- truncate_preview tests ----
-
-    #[test]
-    fn test_truncate_preview_short_string() {
-        assert_eq!(truncate_preview("hello", 10), "hello");
-    }
-
-    #[test]
-    fn test_truncate_preview_exact_boundary() {
-        assert_eq!(truncate_preview("hello", 5), "hello");
-    }
-
-    #[test]
-    fn test_truncate_preview_truncates_ascii() {
-        assert_eq!(truncate_preview("hello world", 5), "hello...");
-    }
-
-    #[test]
-    fn test_truncate_preview_empty_string() {
-        assert_eq!(truncate_preview("", 10), "");
-    }
-
-    #[test]
-    fn test_truncate_preview_multibyte_char_boundary() {
-        // '€' is 3 bytes (E2 82 AC). "a€b" = [61, E2, 82, AC, 62] = 5 bytes
-        // Truncating at max_bytes=3 should not split the euro sign.
-        let s = "a€b";
-        let result = truncate_preview(s, 3);
-        // max_bytes=3 lands mid-€, so it walks back to byte 1 ("a")
-        assert_eq!(result, "a...");
-    }
-
-    #[test]
-    fn test_truncate_preview_emoji() {
-        // '🦀' is 4 bytes. "hi🦀" = 6 bytes
-        let s = "hi🦀";
-        let result = truncate_preview(s, 4);
-        // max_bytes=4 lands mid-🦀, walks back to byte 2 ("hi")
-        assert_eq!(result, "hi...");
-    }
-
-    #[test]
-    fn test_truncate_preview_cjk() {
-        // CJK characters are 3 bytes each. "你好世界" = 12 bytes
-        let s = "你好世界";
-        let result = truncate_preview(s, 7);
-        // max_bytes=7 lands mid-character (byte 7 is inside 世), walks back to 6 ("你好")
-        assert_eq!(result, "你好...");
-    }
-
-    #[test]
-    fn test_truncate_preview_zero_max_bytes() {
-        assert_eq!(truncate_preview("hello", 0), "...");
-    }
-
-    #[test]
-    fn test_truncate_preview_closes_tool_output_tag() {
-        let s = "<tool_output name=\"search\">\nSome very long content here\n</tool_output>";
-        // Truncate so it cuts before the closing tag
-        let result = truncate_preview(s, 60);
-        assert!(result.ends_with("</tool_output>"));
-        assert!(result.contains("..."));
-    }
-
-    #[test]
-    fn test_truncate_preview_no_extra_close_when_intact() {
-        let s = "<tool_output name=\"echo\">\nshort\n</tool_output>";
-        // The string is short enough not to be truncated
-        let result = truncate_preview(s, 500);
-        assert_eq!(result, s);
-        // Should not have a duplicate closing tag
-        assert_eq!(result.matches("</tool_output>").count(), 1);
-    }
-
-    #[test]
-    fn test_truncate_preview_non_xml_unaffected() {
-        let s = "Just a plain long string that gets truncated";
-        let result = truncate_preview(s, 10);
-        assert_eq!(result, "Just a pla...");
-        assert!(!result.contains("</tool_output>"));
-    }
-
    // ---- build_turns_from_db_messages tests ----

    fn make_msg(role: &str, content: &str, offset_ms: i64) -> crate::history::ConversationMessage {
@@ -258,6 +186,29 @@ mod tests {
        assert_eq!(turns[0].response.as_deref(), Some("Done"));
    }

+    #[test]
+    fn test_build_turns_unwrap_wrapped_tool_error_for_display() {
+        let tc_json = serde_json::json!([
+            {
+                "name": "http",
+                "error": "<tool_output name=\"http\">\nTool 'http' failed: timeout\n</tool_output>"
+            }
+        ]);
+        let messages = vec![
+            make_msg("user", "Run it", 0),
+            make_msg("tool_calls", &tc_json.to_string(), 500),
+        ];
+
+        let turns = build_turns_from_db_messages(&messages);
+
+        assert_eq!(turns.len(), 1);
+        assert_eq!(turns[0].tool_calls.len(), 1);
+        assert_eq!(
+            turns[0].tool_calls[0].error.as_deref(),
+            Some("Tool 'http' failed: timeout")
+        );
+    }
+
    #[test]
    fn test_build_turns_malformed_tool_calls() {
        let messages = vec![
@@ -305,4 +256,52 @@ mod tests {
        assert!(turns[0].tool_calls.is_empty());
        assert_eq!(turns[0].state, "Completed");
    }
+
+    #[test]
+    fn test_build_turns_with_wrapped_tool_calls_format() {
+        let tc_json = serde_json::json!({
+            "narrative": "Searching memory for context before proceeding.",
+            "calls": [
+                {"name": "memory_search", "result_preview": "found 3 items", "rationale": "consult prior context"},
+                {"name": "shell", "error": "permission denied"}
+            ]
+        });
+        let messages = vec![
+            make_msg("user", "Find info", 0),
+            make_msg("tool_calls", &tc_json.to_string(), 500),
+            make_msg("assistant", "Here's what I found", 1000),
+        ];
+        let turns = build_turns_from_db_messages(&messages);
+        assert_eq!(turns.len(), 1);
+        assert_eq!(
+            turns[0].narrative.as_deref(),
+            Some("Searching memory for context before proceeding.")
+        );
+        assert_eq!(turns[0].tool_calls.len(), 2);
+        assert_eq!(turns[0].tool_calls[0].name, "memory_search");
+        assert_eq!(
+            turns[0].tool_calls[0].rationale.as_deref(),
+            Some("consult prior context")
+        );
+        assert!(turns[0].tool_calls[0].has_result);
+        assert_eq!(turns[0].tool_calls[1].name, "shell");
+        assert!(turns[0].tool_calls[1].has_error);
+        assert_eq!(turns[0].response.as_deref(), Some("Here's what I found"));
+    }
+
+    #[test]
+    fn test_build_turns_wrapped_format_without_narrative() {
+        let tc_json = serde_json::json!({
+            "calls": [{"name": "echo", "result_preview": "hello"}]
+        });
+        let messages = vec![
+            make_msg("user", "Say hi", 0),
+            make_msg("tool_calls", &tc_json.to_string(), 500),
+            make_msg("assistant", "Done", 1000),
+        ];
+        let turns = build_turns_from_db_messages(&messages);
+        assert_eq!(turns.len(), 1);
+        assert!(turns[0].narrative.is_none());
+        assert_eq!(turns[0].tool_calls.len(), 1);
+    }
 }
@@ -97,7 +97,7 @@ pub async fn handle_ws_connection(
            let msg = tokio::select! {
                event = event_stream.next() => {
                    match event {
-                        Some(sse_event) => WsServerMessage::from_sse_event(&sse_event),
+                        Some(app_event) => WsServerMessage::from_app_event(&app_event),
                        None => break, // Broadcast channel closed
                    }
                }
@@ -275,7 +275,7 @@ async fn handle_client_message(
                        if result.verification.is_some() {
                            state.sse.broadcast_for_user(
                                user_id,
-                                crate::channels::web::types::SseEvent::AuthRequired {
+                                crate::channels::web::types::AppEvent::AuthRequired {
                                    extension_name: extension_name.clone(),
                                    instructions: Some(result.message),
                                    auth_url: None,
@@ -286,7 +286,7 @@ async fn handle_client_message(
                            crate::channels::web::server::clear_auth_mode(state, user_id).await;
                            state.sse.broadcast_for_user(
                                user_id,
-                                crate::channels::web::types::SseEvent::AuthCompleted {
+                                crate::channels::web::types::AppEvent::AuthCompleted {
                                    extension_name,
                                    success: true,
                                    message: result.message,
@@ -299,7 +299,7 @@ async fn handle_client_message(
                        if matches!(e, crate::extensions::ExtensionError::ValidationFailed(_)) {
                            state.sse.broadcast_for_user(
                                user_id,
-                                crate::channels::web::types::SseEvent::AuthRequired {
+                                crate::channels::web::types::AppEvent::AuthRequired {
                                    extension_name: extension_name.clone(),
                                    instructions: Some(msg.clone()),
                                    auth_url: None,
@@ -520,7 +520,7 @@ mod tests {
            job_manager: None,
            prompt_queue: None,
            scheduler: None,
-            default_user_id: "test".to_string(),
+            owner_id: "test".to_string(),
            shutdown_tx: tokio::sync::RwLock::new(None),
            ws_tracker: Some(Arc::new(WsConnectionTracker::new())),
            llm_provider: None,
@@ -534,6 +534,8 @@ mod tests {
            routine_engine: Arc::new(tokio::sync::RwLock::new(None)),
            startup_time: std::time::Instant::now(),
            active_config: crate::channels::web::server::ActiveConfigSnapshot::default(),
+            secrets_store: None,
+            db_auth: None,
        }
    }
 }
@@ -352,7 +352,7 @@ pub async fn run_routines_cli(
        .await
        .map_err(|e| anyhow::anyhow!("{e:#}"))?;

-    let user_id = std::env::var("GATEWAY_USER_ID").unwrap_or_else(|_| "default".to_string());
+    let user_id = std::env::var("IRONCLAW_OWNER_ID").unwrap_or_else(|_| "default".to_string());
    run_routines_command(routines_cmd.clone(), db, &user_id).await
 }

@@ -62,6 +62,30 @@ pub fn builtin_client_id_override_env(secret_name: &str) -> Option<&'static str>
    }
 }

+/// Suppress the baked-in desktop OAuth client secret when a hosted proxy is configured.
+///
+/// In hosted deployments, IronClaw may resolve the platform Google client ID from
+/// environment variables while still falling back to the baked-in desktop secret.
+/// That client_id/client_secret mismatch breaks Google token exchange and refresh.
+///
+/// When the proxy is configured, the platform will inject the correct server-side
+/// secret for matching platform credentials, so the baked-in secret must be omitted.
+pub fn hosted_proxy_client_secret(
+    client_secret: &Option<String>,
+    builtin: Option<&OAuthCredentials>,
+    exchange_proxy_configured: bool,
+) -> Option<String> {
+    if !exchange_proxy_configured {
+        return client_secret.clone();
+    }
+
+    let builtin_secret = builtin.map(|credentials| credentials.client_secret);
+    match (client_secret, builtin_secret) {
+        (Some(resolved), Some(baked_in)) if resolved == baked_in => None,
+        _ => client_secret.clone(),
+    }
+}
+
 // ── Shared callback server ──────────────────────────────────────────────

 // Core OAuth callback infrastructure is defined in `crate::llm::oauth_helpers`
@@ -449,7 +473,8 @@ pub struct PendingOAuthFlow {
    pub secrets: Arc<dyn SecretsStore + Send + Sync>,
    /// SSE broadcast manager for notifying the web UI.
    pub sse_manager: Option<Arc<crate::channels::web::sse::SseManager>>,
-    /// Gateway auth token for authenticating with the platform token exchange proxy.
+    /// OAuth proxy auth token for authenticating with the hosted token exchange proxy.
+    /// Kept as `gateway_token` for public API compatibility.
    pub gateway_token: Option<String>,
    /// Additional form params for the token exchange request.
    /// Used for provider-specific requirements such as RFC 8707 `resource`.
@@ -472,6 +497,12 @@ impl std::fmt::Debug for PendingOAuthFlow {
    }
 }

+impl PendingOAuthFlow {
+    pub fn oauth_proxy_auth_token(&self) -> Option<&str> {
+        self.gateway_token.as_deref()
+    }
+}
+
 /// Thread-safe registry of pending OAuth flows, keyed by CSRF `state` parameter.
 pub type PendingOAuthRegistry = Arc<RwLock<HashMap<String, PendingOAuthFlow>>>;

@@ -505,6 +536,22 @@ pub fn exchange_proxy_url() -> Option<String> {
        .filter(|url| !url.is_empty())
 }

+/// Returns the configured OAuth proxy auth token, if any.
+///
+/// New hosted infra can inject a dedicated shared proxy secret via
+/// `IRONCLAW_OAUTH_PROXY_AUTH_TOKEN`. Existing hosted instances continue to
+/// work by falling back to `GATEWAY_AUTH_TOKEN`.
+pub fn oauth_proxy_auth_token() -> Option<String> {
+    fn normalized_env_value(key: &str) -> Option<String> {
+        crate::config::helpers::env_or_override(key)
+            .map(|value| value.trim().to_string())
+            .filter(|value| !value.is_empty())
+    }
+
+    normalized_env_value("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN")
+        .or_else(|| normalized_env_value("GATEWAY_AUTH_TOKEN"))
+}
+
 /// Maximum age for pending OAuth flows (5 minutes, matching TCP listener timeout).
 pub const OAUTH_FLOW_EXPIRY: Duration = Duration::from_secs(300);

@@ -522,6 +569,42 @@ pub async fn sweep_expired_flows(registry: &PendingOAuthRegistry) {
 const HOSTED_STATE_PREFIX: &str = "ic2";
 const HOSTED_STATE_CHECKSUM_BYTES: usize = 12;

+/// Maximum length for a legacy flow ID or instance name.
+const LEGACY_STATE_MAX_LEN: usize = 128;
+/// Minimum length for a legacy flow ID.
+const LEGACY_STATE_MIN_LEN: usize = 8;
+
+/// Validate that a legacy state component (flow_id or instance_name) contains
+/// only safe characters: alphanumeric, dash, underscore.
+fn is_valid_legacy_state_component(s: &str) -> bool {
+    !s.is_empty()
+        && s.len() <= LEGACY_STATE_MAX_LEN
+        && s.bytes()
+            .all(|b| b.is_ascii_alphanumeric() || b == b'-' || b == b'_')
+}
+
+fn validate_legacy_flow_id(flow_id: &str) -> Result<(), String> {
+    if flow_id.len() < LEGACY_STATE_MIN_LEN {
+        return Err(format!(
+            "Legacy OAuth flow_id too short ({} chars, minimum {LEGACY_STATE_MIN_LEN})",
+            flow_id.len()
+        ));
+    }
+    if flow_id.len() > LEGACY_STATE_MAX_LEN {
+        return Err(format!(
+            "Legacy OAuth flow_id too long ({} chars, maximum {LEGACY_STATE_MAX_LEN})",
+            flow_id.len()
+        ));
+    }
+    if !flow_id
+        .bytes()
+        .all(|b| b.is_ascii_alphanumeric() || b == b'-' || b == b'_')
+    {
+        return Err("Legacy OAuth flow_id contains invalid characters".to_string());
+    }
+    Ok(())
+}
+
 #[derive(Debug, Clone, PartialEq, Eq)]
 pub struct DecodedHostedOAuthState {
    pub flow_id: String,
@@ -606,6 +689,17 @@ pub fn decode_hosted_oauth_state(state: &str) -> Result<DecodedHostedOAuthState,
        if flow_id.is_empty() {
            return Err("Hosted OAuth legacy state is missing flow_id".to_string());
        }
+        validate_legacy_flow_id(flow_id)?;
+        if !instance_name.is_empty() && !is_valid_legacy_state_component(instance_name) {
+            return Err(format!(
+                "Legacy OAuth instance name contains invalid characters or exceeds max length ({LEGACY_STATE_MAX_LEN})"
+            ));
+        }
+        tracing::debug!(
+            flow_id,
+            instance_name,
+            "Decoded legacy prefixed OAuth state"
+        );
        return Ok(DecodedHostedOAuthState {
            flow_id: flow_id.to_string(),
            instance_name: if instance_name.is_empty() {
@@ -621,6 +715,9 @@ pub fn decode_hosted_oauth_state(state: &str) -> Result<DecodedHostedOAuthState,
        return Err("Hosted OAuth state is empty".to_string());
    }

+    validate_legacy_flow_id(state)?;
+    tracing::debug!(flow_id = state, "Decoded legacy raw OAuth state");
+
    Ok(DecodedHostedOAuthState {
        flow_id: state.to_string(),
        instance_name: None,
@@ -650,6 +747,8 @@ pub fn strip_instance_prefix(state: &str) -> &str {

 pub struct ProxyTokenExchangeRequest<'a> {
    pub proxy_url: &'a str,
+    /// OAuth proxy auth token.
+    /// Kept as `gateway_token` for public API compatibility.
    pub gateway_token: &'a str,
    pub token_url: &'a str,
    pub client_id: &'a str,
@@ -661,9 +760,53 @@ pub struct ProxyTokenExchangeRequest<'a> {
    pub extra_token_params: &'a HashMap<String, String>,
 }

+pub struct ProxyRefreshTokenRequest<'a> {
+    pub proxy_url: &'a str,
+    /// OAuth proxy auth token.
+    /// Kept as `gateway_token` for public API compatibility.
+    pub gateway_token: &'a str,
+    pub token_url: &'a str,
+    pub client_id: &'a str,
+    pub client_secret: Option<&'a str>,
+    pub refresh_token: &'a str,
+    pub provider: Option<&'a str>,
+}
+
+fn oauth_token_response_from_json(
+    token_data: serde_json::Value,
+    access_token_field: &str,
+) -> Result<OAuthTokenResponse, OAuthCallbackError> {
+    let access_token = token_data
+        .get(access_token_field)
+        .and_then(|v| v.as_str())
+        .ok_or_else(|| {
+            let fields: Vec<&str> = token_data
+                .as_object()
+                .map(|o| o.keys().map(|k| k.as_str()).collect())
+                .unwrap_or_default();
+            OAuthCallbackError::Io(format!(
+                "No '{}' field in proxy response (fields present: {:?})",
+                access_token_field, fields
+            ))
+        })?
+        .to_string();
+
+    let refresh_token = token_data
+        .get("refresh_token")
+        .and_then(|v| v.as_str())
+        .map(String::from);
+    let expires_in = token_data.get("expires_in").and_then(|v| v.as_u64());
+
+    Ok(OAuthTokenResponse {
+        access_token,
+        refresh_token,
+        expires_in,
+    })
+}
+
 /// Exchange an OAuth authorization code via the platform's token exchange proxy.
 ///
-/// Authenticated via the gateway auth token (Bearer header). The caller may
+/// Authenticated via an OAuth proxy auth token (Bearer header). The caller may
 /// either rely on proxy-side secret lookup or forward a `client_secret` when
 /// the provider requires it.
 ///
@@ -675,13 +818,14 @@ pub async fn exchange_via_proxy(
 ) -> Result<OAuthTokenResponse, OAuthCallbackError> {
    if request.gateway_token.is_empty() {
        return Err(OAuthCallbackError::Io(
-            "Gateway auth token is required for proxy token exchange".to_string(),
+            "OAuth proxy auth token is required for proxy token exchange".to_string(),
        ));
    }
    let exchange_url = format!("{}/oauth/exchange", request.proxy_url.trim_end_matches('/'));

    let client = reqwest::Client::builder()
        .timeout(Duration::from_secs(60))
+        .redirect(reqwest::redirect::Policy::none())
        .build()
        .map_err(|e| OAuthCallbackError::Io(format!("Failed to build HTTP client: {}", e)))?;
    let mut params = vec![
@@ -724,41 +868,454 @@ pub async fn exchange_via_proxy(
        .json()
        .await
        .map_err(|e| OAuthCallbackError::Io(format!("Failed to parse proxy response: {}", e)))?;
+    oauth_token_response_from_json(token_data, request.access_token_field)
+}

-    let access_token = token_data
-        .get(request.access_token_field)
-        .and_then(|v| v.as_str())
-        .ok_or_else(|| {
-            let fields: Vec<&str> = token_data
-                .as_object()
-                .map(|o| o.keys().map(|k| k.as_str()).collect())
-                .unwrap_or_default();
-            OAuthCallbackError::Io(format!(
-                "No '{}' field in proxy response (fields present: {:?})",
-                request.access_token_field, fields
-            ))
-        })?
-        .to_string();
+/// Refresh an OAuth access token via the platform's token refresh proxy.
+///
+/// Authenticated via an OAuth proxy auth token (Bearer header). The caller may
+/// either rely on proxy-side secret lookup or forward a `client_secret` when
+/// the provider requires it.
+pub async fn refresh_token_via_proxy(
+    request: ProxyRefreshTokenRequest<'_>,
+) -> Result<OAuthTokenResponse, OAuthCallbackError> {
+    if request.gateway_token.is_empty() {
+        return Err(OAuthCallbackError::Io(
+            "OAuth proxy auth token is required for proxy token refresh".to_string(),
+        ));
+    }

-    let refresh_token = token_data
-        .get("refresh_token")
-        .and_then(|v| v.as_str())
-        .map(String::from);
-    let expires_in = token_data.get("expires_in").and_then(|v| v.as_u64());
+    let refresh_url = format!("{}/oauth/refresh", request.proxy_url.trim_end_matches('/'));
+    let client = reqwest::Client::builder()
+        .timeout(Duration::from_secs(15))
+        .redirect(reqwest::redirect::Policy::none())
+        .build()
+        .map_err(|e| OAuthCallbackError::Io(format!("Failed to build HTTP client: {}", e)))?;

-    Ok(OAuthTokenResponse {
-        access_token,
-        refresh_token,
-        expires_in,
-    })
+    let mut params = vec![
+        ("refresh_token", request.refresh_token.to_string()),
+        ("token_url", request.token_url.to_string()),
+        ("client_id", request.client_id.to_string()),
+    ];
+    if let Some(secret) = request.client_secret {
+        params.push(("client_secret", secret.to_string()));
+    }
+    if let Some(provider) = request.provider {
+        params.push(("provider", provider.to_string()));
+    }
+
+    let response = client
+        .post(&refresh_url)
+        .bearer_auth(request.gateway_token)
+        .form(&params)
+        .send()
+        .await
+        .map_err(|e| {
+            OAuthCallbackError::Io(format!("Token refresh proxy request failed: {}", e))
+        })?;
+
+    if !response.status().is_success() {
+        let status = response.status();
+        let body = response.text().await.unwrap_or_default();
+        return Err(OAuthCallbackError::Io(format!(
+            "Token refresh proxy failed: {} - {}",
+            status, body
+        )));
+    }
+
+    let token_data: serde_json::Value = response
+        .json()
+        .await
+        .map_err(|e| OAuthCallbackError::Io(format!("Failed to parse proxy response: {}", e)))?;
+
+    oauth_token_response_from_json(token_data, "access_token")
 }

 #[cfg(test)]
 mod tests {
+    use std::collections::HashMap;
+    use std::net::SocketAddr;
+    use std::sync::Arc;
+
+    use axum::extract::{Form, State};
+    use axum::http::HeaderMap;
+    use axum::response::Redirect;
+    use axum::routing::post;
+    use axum::{Json, Router};
+    use serde_json::json;
+    use tokio::net::TcpListener;
+    use tokio::sync::{Mutex, oneshot};
+
    use crate::cli::oauth_defaults::{
        builtin_credentials, callback_host, callback_url, is_loopback_host, landing_html,
    };
    use crate::config::helpers::lock_env;
+    use crate::testing::credentials::{TEST_OAUTH_CLIENT_ID, TEST_OAUTH_CLIENT_SECRET};
+
+    #[derive(Clone, Debug, PartialEq, Eq)]
+    struct RecordedProxyRequest {
+        authorization: Option<String>,
+        form: HashMap<String, String>,
+    }
+
+    #[derive(Clone)]
+    struct MockProxyState {
+        requests: Arc<Mutex<Vec<RecordedProxyRequest>>>,
+        exchange_redirect_target: String,
+        refresh_redirect_target: String,
+    }
+
+    struct MockProxyServer {
+        addr: SocketAddr,
+        requests: Arc<Mutex<Vec<RecordedProxyRequest>>>,
+        shutdown_tx: Option<oneshot::Sender<()>>,
+        server_task: Option<tokio::task::JoinHandle<()>>,
+    }
+
+    impl MockProxyServer {
+        async fn start() -> Self {
+            async fn exchange_handler(
+                State(state): State<MockProxyState>,
+                headers: HeaderMap,
+                Form(form): Form<HashMap<String, String>>,
+            ) -> Json<serde_json::Value> {
+                state.requests.lock().await.push(RecordedProxyRequest {
+                    authorization: headers
+                        .get(axum::http::header::AUTHORIZATION)
+                        .and_then(|value| value.to_str().ok())
+                        .map(str::to_string),
+                    form,
+                });
+                Json(json!({
+                    "access_token": "proxy-access-token",
+                    "refresh_token": "proxy-refresh-token",
+                    "expires_in": 7200
+                }))
+            }
+
+            async fn refresh_handler(
+                State(state): State<MockProxyState>,
+                headers: HeaderMap,
+                Form(form): Form<HashMap<String, String>>,
+            ) -> Json<serde_json::Value> {
+                state.requests.lock().await.push(RecordedProxyRequest {
+                    authorization: headers
+                        .get(axum::http::header::AUTHORIZATION)
+                        .and_then(|value| value.to_str().ok())
+                        .map(str::to_string),
+                    form,
+                });
+                Json(json!({
+                    "access_token": "proxy-access-token",
+                    "refresh_token": "proxy-refresh-token",
+                    "expires_in": 7200
+                }))
+            }
+
+            async fn exchange_redirect_handler(State(state): State<MockProxyState>) -> Redirect {
+                Redirect::temporary(&state.exchange_redirect_target)
+            }
+
+            async fn refresh_redirect_handler(State(state): State<MockProxyState>) -> Redirect {
+                Redirect::temporary(&state.refresh_redirect_target)
+            }
+
+            let requests = Arc::new(Mutex::new(Vec::new()));
+            let listener = TcpListener::bind("127.0.0.1:0")
+                .await
+                .expect("bind mock proxy");
+            let addr = listener.local_addr().expect("read mock proxy addr");
+            let exchange_redirect_target = format!("http://{addr}/oauth/exchange");
+            let refresh_redirect_target = format!("http://{addr}/oauth/refresh");
+            let app = Router::new()
+                .route("/oauth/exchange", post(exchange_handler))
+                .route("/oauth/refresh", post(refresh_handler))
+                .route("/redirect/oauth/exchange", post(exchange_redirect_handler))
+                .route("/redirect/oauth/refresh", post(refresh_redirect_handler))
+                .with_state(MockProxyState {
+                    requests: Arc::clone(&requests),
+                    exchange_redirect_target,
+                    refresh_redirect_target,
+                });
+            let (shutdown_tx, shutdown_rx) = oneshot::channel::<()>();
+            let server_task = tokio::spawn(async move {
+                let _ = axum::serve(listener, app)
+                    .with_graceful_shutdown(async {
+                        let _ = shutdown_rx.await;
+                    })
+                    .await;
+            });
+
+            Self {
+                addr,
+                requests,
+                shutdown_tx: Some(shutdown_tx),
+                server_task: Some(server_task),
+            }
+        }
+
+        fn base_url(&self) -> String {
+            format!("http://{}", self.addr)
+        }
+
+        fn redirecting_base_url(&self) -> String {
+            format!("{}/redirect", self.base_url())
+        }
+
+        async fn requests(&self) -> Vec<RecordedProxyRequest> {
+            self.requests.lock().await.clone()
+        }
+
+        async fn shutdown(mut self) {
+            if let Some(tx) = self.shutdown_tx.take() {
+                let _ = tx.send(());
+            }
+            if let Some(task) = self.server_task.take() {
+                let _ = task.await;
+            }
+        }
+    }
+
+    impl Drop for MockProxyServer {
+        fn drop(&mut self) {
+            if let Some(tx) = self.shutdown_tx.take() {
+                let _ = tx.send(());
+            }
+            if let Some(task) = self.server_task.take() {
+                task.abort();
+            }
+        }
+    }
+
+    struct EnvVarGuard {
+        key: &'static str,
+        original: Option<String>,
+    }
+
+    impl Drop for EnvVarGuard {
+        fn drop(&mut self) {
+            // SAFETY: Under ENV_MUTEX, no concurrent env access.
+            unsafe {
+                if let Some(ref value) = self.original {
+                    std::env::set_var(self.key, value);
+                } else {
+                    std::env::remove_var(self.key);
+                }
+            }
+        }
+    }
+
+    fn set_env_var(key: &'static str, value: Option<&str>) -> EnvVarGuard {
+        let original = std::env::var(key).ok();
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe {
+            if let Some(value) = value {
+                std::env::set_var(key, value);
+            } else {
+                std::env::remove_var(key);
+            }
+        }
+        EnvVarGuard { key, original }
+    }
+
+    #[test]
+    fn test_hosted_proxy_client_secret_suppresses_builtin_secret() {
+        let builtin = builtin_credentials("google_oauth_token").expect("google builtin creds");
+        let client_secret = Some(builtin.client_secret.to_string());
+
+        let result = super::hosted_proxy_client_secret(&client_secret, Some(&builtin), true);
+
+        assert_eq!(result, None);
+    }
+
+    #[test]
+    fn test_hosted_proxy_client_secret_preserves_explicit_secret() {
+        let builtin = builtin_credentials("google_oauth_token").expect("google builtin creds");
+        let client_secret = Some("hosted-server-secret".to_string());
+
+        let result = super::hosted_proxy_client_secret(&client_secret, Some(&builtin), true);
+
+        assert_eq!(result, client_secret);
+    }
+
+    #[tokio::test]
+    async fn test_exchange_via_proxy_sends_auth_and_form() {
+        let server = MockProxyServer::start().await;
+        let mut extra_token_params = HashMap::new();
+        extra_token_params.insert("resource".to_string(), "https://mcp.notion.com".to_string());
+
+        let response = super::exchange_via_proxy(super::ProxyTokenExchangeRequest {
+            proxy_url: &server.base_url(),
+            gateway_token: "shared-oauth-proxy-secret",
+            code: "auth-code-123",
+            redirect_uri: "https://oauth.example.com/oauth/callback",
+            token_url: "https://oauth2.googleapis.com/token",
+            client_id: TEST_OAUTH_CLIENT_ID,
+            client_secret: Some(TEST_OAUTH_CLIENT_SECRET),
+            access_token_field: "access_token",
+            code_verifier: Some("code-verifier-123"),
+            extra_token_params: &extra_token_params,
+        })
+        .await
+        .expect("proxy exchange succeeds");
+
+        assert_eq!(response.access_token, "proxy-access-token");
+        assert_eq!(
+            response.refresh_token.as_deref(),
+            Some("proxy-refresh-token")
+        );
+        assert_eq!(response.expires_in, Some(7200));
+
+        let requests = server.requests().await;
+        assert_eq!(requests.len(), 1);
+        assert_eq!(
+            requests[0].authorization.as_deref(),
+            Some("Bearer shared-oauth-proxy-secret")
+        );
+        assert_eq!(
+            requests[0].form.get("code").map(String::as_str),
+            Some("auth-code-123")
+        );
+        assert_eq!(
+            requests[0].form.get("redirect_uri").map(String::as_str),
+            Some("https://oauth.example.com/oauth/callback")
+        );
+        assert_eq!(
+            requests[0].form.get("token_url").map(String::as_str),
+            Some("https://oauth2.googleapis.com/token")
+        );
+        assert_eq!(
+            requests[0].form.get("client_id").map(String::as_str),
+            Some(TEST_OAUTH_CLIENT_ID)
+        );
+        assert_eq!(
+            requests[0].form.get("client_secret").map(String::as_str),
+            Some(TEST_OAUTH_CLIENT_SECRET)
+        );
+        assert_eq!(
+            requests[0]
+                .form
+                .get("access_token_field")
+                .map(String::as_str),
+            Some("access_token")
+        );
+        assert_eq!(
+            requests[0].form.get("code_verifier").map(String::as_str),
+            Some("code-verifier-123")
+        );
+        assert_eq!(
+            requests[0].form.get("resource").map(String::as_str),
+            Some("https://mcp.notion.com")
+        );
+
+        server.shutdown().await;
+    }
+
+    #[tokio::test]
+    async fn test_refresh_token_via_proxy_sends_auth_and_form() {
+        let server = MockProxyServer::start().await;
+
+        let response = super::refresh_token_via_proxy(super::ProxyRefreshTokenRequest {
+            proxy_url: &server.base_url(),
+            gateway_token: "gateway-test-token",
+            token_url: "https://oauth2.googleapis.com/token",
+            client_id: TEST_OAUTH_CLIENT_ID,
+            client_secret: Some(TEST_OAUTH_CLIENT_SECRET),
+            refresh_token: "refresh-token-123",
+            provider: Some("google"),
+        })
+        .await
+        .expect("proxy refresh succeeds");
+
+        assert_eq!(response.access_token, "proxy-access-token");
+        assert_eq!(
+            response.refresh_token.as_deref(),
+            Some("proxy-refresh-token")
+        );
+        assert_eq!(response.expires_in, Some(7200));
+
+        let requests = server.requests().await;
+        assert_eq!(requests.len(), 1);
+        assert_eq!(
+            requests[0].authorization.as_deref(),
+            Some("Bearer gateway-test-token")
+        );
+        assert_eq!(
+            requests[0].form.get("token_url").map(String::as_str),
+            Some("https://oauth2.googleapis.com/token")
+        );
+        assert_eq!(
+            requests[0].form.get("client_id").map(String::as_str),
+            Some(TEST_OAUTH_CLIENT_ID)
+        );
+        assert_eq!(
+            requests[0].form.get("client_secret").map(String::as_str),
+            Some(TEST_OAUTH_CLIENT_SECRET)
+        );
+        assert_eq!(
+            requests[0].form.get("refresh_token").map(String::as_str),
+            Some("refresh-token-123")
+        );
+        assert_eq!(
+            requests[0].form.get("provider").map(String::as_str),
+            Some("google")
+        );
+
+        server.shutdown().await;
+    }
+
+    #[tokio::test]
+    async fn test_exchange_via_proxy_does_not_follow_redirects() {
+        let server = MockProxyServer::start().await;
+
+        let error = match super::exchange_via_proxy(super::ProxyTokenExchangeRequest {
+            proxy_url: &server.redirecting_base_url(),
+            gateway_token: "gateway-test-token",
+            code: "auth-code-123",
+            redirect_uri: "http://localhost:3000/oauth/callback",
+            token_url: "https://oauth2.googleapis.com/token",
+            client_id: TEST_OAUTH_CLIENT_ID,
+            client_secret: Some(TEST_OAUTH_CLIENT_SECRET),
+            access_token_field: "access_token",
+            code_verifier: Some("code-verifier-123"),
+            extra_token_params: &HashMap::new(),
+        })
+        .await
+        {
+            Ok(_) => panic!("redirected proxy exchange should fail"),
+            Err(error) => error,
+        };
+
+        assert!(error.to_string().contains("307"));
+        assert!(server.requests().await.is_empty());
+
+        server.shutdown().await;
+    }
+
+    #[tokio::test]
+    async fn test_refresh_token_via_proxy_does_not_follow_redirects() {
+        let server = MockProxyServer::start().await;
+
+        let error = match super::refresh_token_via_proxy(super::ProxyRefreshTokenRequest {
+            proxy_url: &server.redirecting_base_url(),
+            gateway_token: "gateway-test-token",
+            token_url: "https://oauth2.googleapis.com/token",
+            client_id: TEST_OAUTH_CLIENT_ID,
+            client_secret: Some(TEST_OAUTH_CLIENT_SECRET),
+            refresh_token: "refresh-token-123",
+            provider: Some("google"),
+        })
+        .await
+        {
+            Ok(_) => panic!("redirected proxy refresh should fail"),
+            Err(error) => error,
+        };
+
+        assert!(error.to_string().contains("307"));
+        assert!(server.requests().await.is_empty());
+
+        server.shutdown().await;
+    }

    #[test]
    fn test_is_loopback_host() {
@@ -1159,6 +1716,54 @@ mod tests {
        }
    }

+    #[test]
+    fn test_oauth_proxy_auth_token_prefers_dedicated_env() {
+        let _guard = lock_env();
+        let _proxy_guard = set_env_var(
+            "IRONCLAW_OAUTH_PROXY_AUTH_TOKEN",
+            Some("shared-proxy-secret"),
+        );
+        let _gateway_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-token"));
+
+        assert_eq!(
+            crate::cli::oauth_defaults::oauth_proxy_auth_token().as_deref(),
+            Some("shared-proxy-secret")
+        );
+    }
+
+    #[test]
+    fn test_oauth_proxy_auth_token_falls_back_to_gateway_token() {
+        let _guard = lock_env();
+        let _proxy_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", None);
+        let _gateway_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-token"));
+
+        assert_eq!(
+            crate::cli::oauth_defaults::oauth_proxy_auth_token().as_deref(),
+            Some("gateway-token")
+        );
+    }
+
+    #[test]
+    fn test_oauth_proxy_auth_token_whitespace_dedicated_env_falls_back_to_gateway_token() {
+        let _guard = lock_env();
+        let _proxy_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", Some("   "));
+        let _gateway_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-token"));
+
+        assert_eq!(
+            crate::cli::oauth_defaults::oauth_proxy_auth_token().as_deref(),
+            Some("gateway-token")
+        );
+    }
+
+    #[test]
+    fn test_oauth_proxy_auth_token_returns_none_when_unset() {
+        let _guard = lock_env();
+        let _proxy_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", None);
+        let _gateway_guard = set_env_var("GATEWAY_AUTH_TOKEN", None);
+
+        assert_eq!(crate::cli::oauth_defaults::oauth_proxy_auth_token(), None);
+    }
+
    #[test]
    fn test_strip_instance_prefix_with_colon() {
        use crate::cli::oauth_defaults::strip_instance_prefix;
@@ -1179,13 +1784,13 @@ mod tests {
    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");
+        let decoded = decode_hosted_oauth_state("kind-deer:abc12345").expect("legacy prefixed");
+        assert_eq!(decoded.flow_id, "abc12345");
        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");
+        let decoded = decode_hosted_oauth_state("abc12345").expect("legacy raw");
+        assert_eq!(decoded.flow_id, "abc12345");
        assert_eq!(decoded.instance_name, None);
        assert!(decoded.is_legacy);
    }
@@ -1309,4 +1914,72 @@ mod tests {
        assert_eq!(decoded_no_instance.instance_name, None);
        assert!(!decoded_no_instance.is_legacy);
    }
+
+    /// Legacy flow IDs that are too short must be rejected (#1443).
+    #[test]
+    fn test_legacy_state_rejects_short_flow_id() {
+        use crate::cli::oauth_defaults::decode_hosted_oauth_state;
+
+        let err = decode_hosted_oauth_state("abc").expect_err("short raw flow_id");
+        assert!(err.contains("too short"), "unexpected error: {err}");
+
+        let err = decode_hosted_oauth_state("inst:abc").expect_err("short prefixed flow_id");
+        assert!(err.contains("too short"), "unexpected error: {err}");
+    }
+
+    /// Legacy flow IDs with invalid characters must be rejected (#1443).
+    #[test]
+    fn test_legacy_state_rejects_invalid_characters() {
+        use crate::cli::oauth_defaults::decode_hosted_oauth_state;
+
+        let err = decode_hosted_oauth_state("flow id with spaces!").expect_err("spaces in flow_id");
+        assert!(
+            err.contains("invalid characters"),
+            "unexpected error: {err}"
+        );
+
+        let err = decode_hosted_oauth_state("inst:flow/id?bad=yes")
+            .expect_err("special chars in prefixed flow_id");
+        assert!(
+            err.contains("invalid characters"),
+            "unexpected error: {err}"
+        );
+    }
+
+    /// Legacy instance names with invalid characters must be rejected (#1444).
+    #[test]
+    fn test_legacy_state_rejects_invalid_instance_name() {
+        use crate::cli::oauth_defaults::decode_hosted_oauth_state;
+
+        let err = decode_hosted_oauth_state("bad instance!:valid-flow-id-12345")
+            .expect_err("invalid instance name");
+        assert!(err.contains("instance name"), "unexpected error: {err}");
+    }
+
+    /// Excessively long legacy flow IDs must be rejected (#1443).
+    #[test]
+    fn test_legacy_state_rejects_oversized_flow_id() {
+        use crate::cli::oauth_defaults::decode_hosted_oauth_state;
+
+        let long_id = "a".repeat(200);
+        let err = decode_hosted_oauth_state(&long_id).expect_err("oversized flow_id");
+        assert!(err.contains("too long"), "unexpected error: {err}");
+    }
+
+    /// Valid legacy flow IDs at boundary lengths are accepted.
+    #[test]
+    fn test_legacy_state_accepts_boundary_lengths() {
+        use crate::cli::oauth_defaults::decode_hosted_oauth_state;
+
+        // Exactly 8 chars (minimum)
+        let decoded = decode_hosted_oauth_state("abcd1234").expect("8-char flow_id");
+        assert_eq!(decoded.flow_id, "abcd1234");
+        assert!(decoded.is_legacy);
+
+        // Exactly 128 chars (maximum)
+        let max_id = "a".repeat(128);
+        let decoded = decode_hosted_oauth_state(&max_id).expect("128-char flow_id");
+        assert_eq!(decoded.flow_id, max_id);
+        assert!(decoded.is_legacy);
+    }
 }
@@ -10,7 +10,7 @@ use clap::Subcommand;
 use uuid::Uuid;

 use crate::agent::routine::{
-    NotifyConfig, Routine, RoutineAction, RoutineGuardrails, Trigger, next_cron_fire,
+    NotifyConfig, Routine, RoutineAction, RoutineGuardrails, RunStatus, Trigger, next_cron_fire,
 };
 use crate::db::Database;

@@ -251,15 +251,26 @@ async fn list(
    );
    println!("{}", "-".repeat(130));

+    // Fetch last-run status for all routines in a single batch query
+    let routine_ids: Vec<Uuid> = filtered.iter().map(|r| r.id).collect();
+    let last_run_results = db
+        .batch_get_last_run_status(&routine_ids)
+        .await
+        .unwrap_or_default();
+
    for r in &filtered {
-        let status = if r.enabled {
-            if r.consecutive_failures > 0 {
-                format!("err({})", r.consecutive_failures)
-            } else {
-                "active".to_string()
-            }
-        } else {
+        let last_run_status = last_run_results.get(&r.id).copied();
+
+        let status = if !r.enabled {
            "disabled".to_string()
+        } else if last_run_status == Some(RunStatus::Running) {
+            "running".to_string()
+        } else if r.consecutive_failures > 0 {
+            format!("err({})", r.consecutive_failures)
+        } else if last_run_status == Some(RunStatus::Attention) {
+            "attention".to_string()
+        } else {
+            "active".to_string()
        };

        let next_fire = r
@@ -2,6 +2,7 @@
 //!
 //! Commands for installing, listing, removing, and authenticating WASM tools.

+use std::collections::{HashMap, HashSet};
 use std::io::Write;
 use std::path::{Path, PathBuf};
 use std::sync::Arc;
@@ -79,6 +80,10 @@ pub enum ToolCommand {
        /// Directory to look for tool (default: ~/.ironclaw/tools/)
        #[arg(short, long)]
        dir: Option<PathBuf>,
+
+        /// User ID for checking credential status (default: "default")
+        #[arg(short, long, default_value = "default")]
+        user: String,
    },

    /// Configure authentication for a tool
@@ -124,7 +129,11 @@ pub async fn run_tool_command(cmd: ToolCommand) -> anyhow::Result<()> {
        } => install_tool(path, name, capabilities, target, release, skip_build, force).await,
        ToolCommand::List { dir, verbose } => list_tools(dir, verbose).await,
        ToolCommand::Remove { name, dir } => remove_tool(name, dir).await,
-        ToolCommand::Info { name_or_path, dir } => show_tool_info(name_or_path, dir).await,
+        ToolCommand::Info {
+            name_or_path,
+            dir,
+            user,
+        } => show_tool_info(name_or_path, dir, user).await,
        ToolCommand::Auth { name, dir, user } => auth_tool(name, dir, user).await,
        ToolCommand::Setup { name, dir, user } => setup_tool(name, dir, user).await,
    }
@@ -388,7 +397,11 @@ async fn remove_tool(name: String, dir: Option<PathBuf>) -> anyhow::Result<()> {
 }

 /// Show information about a tool.
-async fn show_tool_info(name_or_path: String, dir: Option<PathBuf>) -> anyhow::Result<()> {
+async fn show_tool_info(
+    name_or_path: String,
+    dir: Option<PathBuf>,
+    user_id: String,
+) -> anyhow::Result<()> {
    let wasm_path = if name_or_path.ends_with(".wasm") {
        PathBuf::from(&name_or_path)
    } else {
@@ -423,7 +436,37 @@ async fn show_tool_info(name_or_path: String, dir: Option<PathBuf>) -> anyhow::R
        println!("\nCapabilities ({}):", caps_path.display());
        let content = fs::read_to_string(&caps_path).await?;
        match CapabilitiesFile::from_json(&content) {
-            Ok(caps) => print_capabilities_detail(&caps),
+            Ok(caps) => {
+                // Lazily init secrets store only when auth secrets need checking.
+                let has_auth = caps.auth.is_some()
+                    || caps
+                        .setup
+                        .as_ref()
+                        .is_some_and(|s| !s.required_secrets.is_empty())
+                    || caps
+                        .http
+                        .as_ref()
+                        .is_some_and(|h| !h.credentials.is_empty());
+                let secrets_store = if has_auth {
+                    match init_secrets_store().await {
+                        Ok(store) => Some(store),
+                        Err(e) => {
+                            eprintln!("  Warning: could not init secrets store: {}", e);
+                            None
+                        }
+                    }
+                } else {
+                    None
+                };
+                print_capabilities_detail(
+                    &caps,
+                    secrets_store
+                        .as_ref()
+                        .map(|s| s.as_ref() as &(dyn SecretsStore + Send + Sync)),
+                    &user_id,
+                )
+                .await;
+            }
            Err(e) => println!("  Error parsing: {}", e),
        }
    } else {
@@ -476,8 +519,89 @@ fn print_capabilities_summary(caps: &CapabilitiesFile) {
    }
 }

+/// Per-secret info collected from all auth-related capability sections.
+struct AuthSecretInfo {
+    secret_name: String,
+    /// Human-readable label (from auth.display_name or setup prompt).
+    description: Option<String>,
+    /// Injection location (from http.credentials).
+    location: Option<String>,
+}
+
+/// Collected auth secrets and the set of secret names they cover.
+struct CollectedAuthSecrets {
+    secrets: Vec<AuthSecretInfo>,
+    /// Secret names present in `secrets`, for filtering the Secrets capability section.
+    seen_names: HashSet<String>,
+}
+
+/// Collect and deduplicate auth secrets from all auth-related capability sections.
+///
+/// Priority for the description label: auth.display_name > setup.required_secrets.prompt.
+/// Injection location is merged from http.credentials.
+fn collect_auth_secrets(caps: &CapabilitiesFile) -> CollectedAuthSecrets {
+    let mut secrets: Vec<AuthSecretInfo> = Vec::new();
+    let mut seen: HashMap<String, usize> = HashMap::new();
+
+    // auth.display_name is the best label — seed first.
+    if let Some(ref auth) = caps.auth {
+        let index = secrets.len();
+        seen.insert(auth.secret_name.clone(), index);
+        secrets.push(AuthSecretInfo {
+            secret_name: auth.secret_name.clone(),
+            description: auth.display_name.clone(),
+            location: None,
+        });
+    }
+
+    // setup.required_secrets.prompt is second-best label.
+    if let Some(ref setup) = caps.setup {
+        for secret in &setup.required_secrets {
+            if !seen.contains_key(&secret.name) {
+                let index = secrets.len();
+                seen.insert(secret.name.clone(), index);
+                secrets.push(AuthSecretInfo {
+                    secret_name: secret.name.clone(),
+                    description: Some(secret.prompt.clone()),
+                    location: None,
+                });
+            }
+        }
+    }
+
+    // Merge injection location from http.credentials.
+    if let Some(ref http) = caps.http {
+        for cred in http.credentials.values() {
+            let loc = format!("{:?}", cred.location);
+            if let Some(&index) = seen.get(&cred.secret_name) {
+                secrets[index].location = Some(loc);
+            } else {
+                let index = secrets.len();
+                seen.insert(cred.secret_name.clone(), index);
+                secrets.push(AuthSecretInfo {
+                    secret_name: cred.secret_name.clone(),
+                    description: None,
+                    location: Some(loc),
+                });
+            }
+        }
+    }
+
+    let seen_names = seen.into_keys().collect();
+    CollectedAuthSecrets {
+        secrets,
+        seen_names,
+    }
+}
+
 /// Print detailed capabilities.
-fn print_capabilities_detail(caps: &CapabilitiesFile) {
+async fn print_capabilities_detail(
+    caps: &CapabilitiesFile,
+    secrets_store: Option<&(dyn SecretsStore + Send + Sync)>,
+    user_id: &str,
+) {
+    let mut collected = collect_auth_secrets(caps);
+
    if let Some(ref http) = caps.http {
        println!("  HTTP:");
        for endpoint in &http.allowlist {
@@ -490,13 +614,6 @@ fn print_capabilities_detail(caps: &CapabilitiesFile) {
            println!("    {} {} {}", methods, endpoint.host, path);
        }

-        if !http.credentials.is_empty() {
-            println!("  Credentials:");
-            for (key, cred) in &http.credentials {
-                println!("    {}: {} -> {:?}", key, cred.secret_name, cred.location);
-            }
-        }
-
        if let Some(ref rate) = http.rate_limit {
            println!(
                "  Rate limit: {}/min, {}/hour",
@@ -505,12 +622,24 @@ fn print_capabilities_detail(caps: &CapabilitiesFile) {
        }
    }

+    // Filter secrets already covered by the auth section (always rendered when non-empty).
    if let Some(ref secrets) = caps.secrets
        && !secrets.allowed_names.is_empty()
    {
-        println!("  Secrets (existence check only):");
-        for name in &secrets.allowed_names {
-            println!("    {}", name);
+        let extra: Vec<_> = if collected.secrets.is_empty() {
+            secrets.allowed_names.iter().collect()
+        } else {
+            secrets
+                .allowed_names
+                .iter()
+                .filter(|name| !collected.seen_names.contains(name.as_str()))
+                .collect()
+        };
+        if !extra.is_empty() {
+            println!("  Secrets (existence check only):");
+            for name in extra {
+                println!("    {}", name);
+            }
        }
    }

@@ -531,6 +660,38 @@ fn print_capabilities_detail(caps: &CapabilitiesFile) {
            println!("    {}", prefix);
        }
    }
+
+    // Consolidated auth status — sorted by secret name for deterministic output.
+    if !collected.secrets.is_empty() {
+        collected
+            .secrets
+            .sort_by(|a, b| a.secret_name.cmp(&b.secret_name));
+        println!("  Auth:");
+        for info in &collected.secrets {
+            let (icon, label) = match secrets_store {
+                Some(store) => match store.exists(user_id, &info.secret_name).await {
+                    Ok(true) => ("\u{2713}", "configured"),
+                    Ok(false) => ("\u{2717}", "missing"),
+                    Err(e) => {
+                        eprintln!(
+                            "  Warning: failed to check secret `{}`: {}",
+                            info.secret_name, e
+                        );
+                        ("?", "unknown")
+                    }
+                },
+                None => ("?", "unknown"),
+            };
+            let mut parts = info.secret_name.clone();
+            if let Some(ref desc) = info.description {
+                parts = format!("{} ({})", parts, desc);
+            }
+            if let Some(ref loc) = info.location {
+                parts = format!("{} -> {}", parts, loc);
+            }
+            println!("    {}  {} {}", parts, icon, label);
+        }
+    }
 }

 /// Validate a tool name to prevent path traversal.
@@ -677,8 +838,7 @@ async fn combine_provider_scopes(
    secret_name: &str,
    base_oauth: &crate::tools::wasm::OAuthConfigSchema,
 ) -> crate::tools::wasm::OAuthConfigSchema {
-    let mut all_scopes: std::collections::HashSet<String> =
-        base_oauth.scopes.iter().cloned().collect();
+    let mut all_scopes: HashSet<String> = base_oauth.scopes.iter().cloned().collect();

    if let Ok(mut entries) = tokio::fs::read_dir(tools_dir).await {
        while let Ok(Some(entry)) = entries.next_entry().await {
@@ -1127,6 +1287,8 @@ async fn setup_tool(name: String, dir: Option<PathBuf>, user_id: String) -> anyh
 #[cfg(test)]
 mod tests {
    use super::*;
+    use crate::secrets::{CreateSecretParams, SecretsStore};
+    use crate::testing::credentials::test_secrets_store;

    #[test]
    fn test_format_size() {
@@ -1143,4 +1305,96 @@ mod tests {
        assert!(dir.to_string_lossy().contains(".ironclaw"));
        assert!(dir.to_string_lossy().contains("tools"));
    }
+
+    /// Verify that auth secrets are deduplicated across auth, setup, and http.credentials,
+    /// and that credential status is checked against the secrets store.
+    #[tokio::test]
+    async fn test_auth_secret_dedup_and_status() {
+        let caps = CapabilitiesFile::from_json(
+            r#"{
+                "auth": {
+                    "secret_name": "gh_token",
+                    "display_name": "GitHub"
+                },
+                "setup": {
+                    "required_secrets": [
+                        { "name": "gh_token", "prompt": "GitHub PAT" },
+                        { "name": "extra_key", "prompt": "Extra API Key" }
+                    ]
+                },
+                "http": {
+                    "allowlist": [{ "host": "api.github.com" }],
+                    "credentials": {
+                        "github": {
+                            "secret_name": "gh_token",
+                            "location": { "type": "bearer" },
+                            "host_patterns": ["api.github.com"]
+                        }
+                    }
+                },
+                "secrets": {
+                    "allowed_names": ["gh_token", "gh_*"]
+                }
+            }"#,
+        )
+        .unwrap();
+
+        let collected = collect_auth_secrets(&caps);
+
+        // gh_token should appear once (from auth), with location merged from credentials.
+        // extra_key should appear once (from setup).
+        assert_eq!(collected.secrets.len(), 2);
+        let gh = collected
+            .secrets
+            .iter()
+            .find(|s| s.secret_name == "gh_token")
+            .unwrap();
+        assert_eq!(gh.description.as_deref(), Some("GitHub"));
+        assert!(
+            gh.location.is_some(),
+            "location should be merged from http.credentials"
+        );
+
+        let extra = collected
+            .secrets
+            .iter()
+            .find(|s| s.secret_name == "extra_key")
+            .unwrap();
+        assert_eq!(extra.description.as_deref(), Some("Extra API Key"));
+        assert!(extra.location.is_none());
+
+        // Secrets section should filter gh_token (in seen_names) but keep gh_* (wildcard).
+        let secrets = caps.secrets.as_ref().unwrap();
+        let extra_secrets: Vec<_> = secrets
+            .allowed_names
+            .iter()
+            .filter(|name| !collected.seen_names.contains(name.as_str()))
+            .collect();
+        assert_eq!(extra_secrets, vec!["gh_*"]);
+
+        // Verify store check: missing secret -> exists returns false.
+        let store = test_secrets_store();
+        assert!(!store.exists("default", "gh_token").await.unwrap());
+
+        // Store gh_token and verify it's found.
+        store
+            .create(
+                "default",
+                CreateSecretParams::new("gh_token", "ghp_test123"),
+            )
+            .await
+            .unwrap();
+        assert!(store.exists("default", "gh_token").await.unwrap());
+        // extra_key still missing.
+        assert!(!store.exists("default", "extra_key").await.unwrap());
+    }
+
+    /// No auth sections → collect_auth_secrets returns empty.
+    #[test]
+    fn test_collect_auth_secrets_empty_caps() {
+        let caps = CapabilitiesFile::default();
+        let collected = collect_auth_secrets(&caps);
+        assert!(collected.secrets.is_empty());
+        assert!(collected.seen_names.is_empty());
+    }
 }
@@ -1,6 +1,6 @@
 use std::time::Duration;

-use crate::config::helpers::{optional_env, parse_bool_env, parse_option_env, parse_optional_env};
+use crate::config::helpers::{parse_bool_env, parse_option_env, parse_optional_env};
 use crate::error::ConfigError;
 use crate::settings::Settings;

@@ -31,11 +31,17 @@ pub struct AgentConfig {
    pub auto_approve_tools: bool,
    /// Default timezone for new sessions (IANA name, e.g. "America/New_York").
    pub default_timezone: String,
+    /// Maximum concurrent jobs per user. None = use global max_parallel_jobs.
+    pub max_jobs_per_user: Option<usize>,
    /// Maximum tokens per job (0 = unlimited).
    pub max_tokens_per_job: u64,
    /// Whether the deployment is multi-tenant (multiple users sharing one
-    /// instance). Auto-detected from GATEWAY_USER_TOKENS presence.
+    /// instance). Defaults to false; can be set via AGENT_MULTI_TENANT env var.
    pub multi_tenant: bool,
+    /// Maximum concurrent LLM calls per user. None = use default (4).
+    pub max_llm_concurrent_per_user: Option<usize>,
+    /// Maximum concurrent jobs per user. None = use default (3).
+    pub max_jobs_concurrent_per_user: Option<usize>,
 }

 impl AgentConfig {
@@ -58,8 +64,11 @@ impl AgentConfig {
            max_tool_iterations: 10,
            auto_approve_tools: true,
            default_timezone: "UTC".to_string(),
+            max_jobs_per_user: None,
            max_tokens_per_job: 0,
            multi_tenant: false,
+            max_llm_concurrent_per_user: None,
+            max_jobs_concurrent_per_user: None,
        }
    }

@@ -116,14 +125,14 @@ impl AgentConfig {
                }
                tz
            },
+            max_jobs_per_user: parse_option_env("MAX_JOBS_PER_USER")?,
            max_tokens_per_job: parse_optional_env(
                "AGENT_MAX_TOKENS_PER_JOB",
                settings.agent.max_tokens_per_job,
            )?,
-            multi_tenant: parse_bool_env(
-                "MULTI_TENANT",
-                optional_env("GATEWAY_USER_TOKENS")?.is_some(),
-            )?,
+            multi_tenant: parse_bool_env("AGENT_MULTI_TENANT", false)?,
+            max_llm_concurrent_per_user: parse_option_env("TENANT_MAX_LLM_CONCURRENT")?,
+            max_jobs_concurrent_per_user: parse_option_env("TENANT_MAX_JOBS_CONCURRENT")?,
        })
    }
 }
@@ -1,13 +1,11 @@
 use std::collections::HashMap;
 use std::path::PathBuf;

-use secrecy::SecretString;
-use serde::Deserialize;
-
 use crate::bootstrap::ironclaw_base_dir;
 use crate::config::helpers::{optional_env, parse_bool_env, parse_optional_env};
 use crate::error::ConfigError;
 use crate::settings::Settings;
+use secrecy::SecretString;

 /// Channel configurations.
 #[derive(Debug, Clone)]
@@ -45,27 +43,15 @@ pub struct GatewayConfig {
    pub port: u16,
    /// Bearer token for authentication. Random hex generated at startup if unset.
    pub auth_token: Option<String>,
-    pub user_id: String,
    /// Additional user scopes for workspace reads.
    ///
    /// When set, the workspace will be able to read (search, read, list) from
-    /// these additional user scopes while writes remain isolated to `user_id`.
+    /// these additional user scopes while writes remain isolated to the
+    /// authenticated user's own scope.
    /// Parsed from `WORKSPACE_READ_SCOPES` (comma-separated).
    pub workspace_read_scopes: Vec<String>,
    /// Memory layer definitions (JSON in env var, or from external config).
    pub memory_layers: Vec<crate::workspace::layer::MemoryLayer>,
-    /// Multi-user token map. When set, each token maps to a user identity.
-    /// Parsed from `GATEWAY_USER_TOKENS` (JSON string). When absent, falls back
-    /// to single-user mode via `auth_token` + `user_id`.
-    pub user_tokens: Option<HashMap<String, UserTokenConfig>>,
-}
-
-/// Per-user token configuration for multi-user mode.
-#[derive(Debug, Clone, Deserialize)]
-pub struct UserTokenConfig {
-    pub user_id: String,
-    #[serde(default)]
-    pub workspace_read_scopes: Vec<String>,
 }

 /// Signal channel configuration (signal-cli daemon HTTP/JSON-RPC).
@@ -132,10 +118,6 @@ impl ChannelsConfig {

        let gateway_enabled = parse_bool_env("GATEWAY_ENABLED", cs.gateway_enabled)?;
        let gateway = if gateway_enabled {
-            let user_id = optional_env("GATEWAY_USER_ID")?
-                .or_else(|| cs.gateway_user_id.clone())
-                .unwrap_or_else(|| owner_id.to_string());
-
            let memory_layers: Vec<crate::workspace::layer::MemoryLayer> =
                match optional_env("MEMORY_LAYERS")? {
                    Some(json_str) => {
@@ -144,7 +126,7 @@ impl ChannelsConfig {
                            message: format!("must be valid JSON array of layer objects: {e}"),
                        })?
                    }
-                    None => crate::workspace::layer::MemoryLayer::default_for_user(&user_id),
+                    None => crate::workspace::layer::MemoryLayer::default_for_user(owner_id),
                };

            // Validate layer names and scopes
@@ -196,41 +178,6 @@ impl ChannelsConfig {
                }
            }

-            let user_tokens: Option<HashMap<String, UserTokenConfig>> =
-                match optional_env("GATEWAY_USER_TOKENS")? {
-                    Some(json_str) => {
-                        let tokens: HashMap<String, UserTokenConfig> = serde_json::from_str(
-                            &json_str,
-                        )
-                        .map_err(|e| ConfigError::InvalidValue {
-                            key: "GATEWAY_USER_TOKENS".to_string(),
-                            message: format!(
-                                "must be valid JSON object mapping tokens to user configs: {e}"
-                            ),
-                        })?;
-                        if tokens.is_empty() {
-                            return Err(ConfigError::InvalidValue {
-                            key: "GATEWAY_USER_TOKENS".to_string(),
-                            message:
-                                "token map is empty — remove the variable to use single-user mode"
-                                    .to_string(),
-                        });
-                        }
-                        for (tok, cfg) in &tokens {
-                            if cfg.user_id.trim().is_empty() {
-                                return Err(ConfigError::InvalidValue {
-                                    key: "GATEWAY_USER_TOKENS".to_string(),
-                                    message: format!(
-                                        "token '{}...' has an empty user_id",
-                                        &tok[..tok.len().min(8)]
-                                    ),
-                                });
-                            }
-                        }
-                        Some(tokens)
-                    }
-                    None => None,
-                };
            let workspace_read_scopes: Vec<String> = optional_env("WORKSPACE_READ_SCOPES")?
                .map(|s| {
                    s.split(',')
@@ -258,10 +205,8 @@ impl ChannelsConfig {
                )?,
                auth_token: optional_env("GATEWAY_AUTH_TOKEN")?
                    .or_else(|| cs.gateway_auth_token.clone()),
-                user_id,
                workspace_read_scopes,
                memory_layers,
-                user_tokens,
            })
        } else {
            None
@@ -416,15 +361,12 @@ mod tests {
            host: "127.0.0.1".to_string(),
            port: 3000,
            auth_token: Some("tok-abc".to_string()),
-            user_id: "default".to_string(),
            workspace_read_scopes: vec![],
            memory_layers: vec![],
-            user_tokens: None,
        };
        assert_eq!(cfg.host, "127.0.0.1");
        assert_eq!(cfg.port, 3000);
        assert_eq!(cfg.auth_token.as_deref(), Some("tok-abc"));
-        assert_eq!(cfg.user_id, "default");
    }

    #[test]
@@ -433,10 +375,8 @@ mod tests {
            host: "0.0.0.0".to_string(),
            port: 3001,
            auth_token: None,
-            user_id: "anon".to_string(),
            workspace_read_scopes: vec![],
            memory_layers: vec![],
-            user_tokens: None,
        };
        assert!(cfg.auth_token.is_none());
    }
@@ -563,7 +503,6 @@ mod tests {
        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");
@@ -21,8 +21,8 @@ pub struct HeartbeatConfig {
    pub quiet_hours_end: Option<u32>,
    /// Timezone for fire_at and quiet hours evaluation (IANA name).
    pub timezone: Option<String>,
-    /// When true, cycle through all users with routines. Auto-detected from
-    /// GATEWAY_USER_TOKENS or set explicitly via HEARTBEAT_MULTI_TENANT.
+    /// When true, cycle through all users with routines. Controlled via
+    /// HEARTBEAT_MULTI_TENANT env var; defaults to false.
    pub multi_tenant: bool,
 }

@@ -105,12 +105,7 @@ impl HeartbeatConfig {
                }
                tz
            },
-            // Auto-detect multi-tenant mode from GATEWAY_USER_TOKENS presence,
-            // or allow explicit override via HEARTBEAT_MULTI_TENANT.
-            multi_tenant: parse_bool_env(
-                "HEARTBEAT_MULTI_TENANT",
-                optional_env("GATEWAY_USER_TOKENS")?.is_some(),
-            )?,
+            multi_tenant: parse_bool_env("HEARTBEAT_MULTI_TENANT", false)?,
        })
    }
 }
@@ -312,13 +312,11 @@ impl Config {
        let tunnel = TunnelConfig::resolve(settings)?;
        let channels = ChannelsConfig::resolve(settings, &owner_id)?;

-        // Resolve workspace config using the gateway user_id for default layers.
-        let workspace_user_id = channels
-            .gateway
-            .as_ref()
-            .map(|gw| gw.user_id.as_str())
-            .unwrap_or("default");
-        let workspace = WorkspaceConfig::resolve(workspace_user_id)?;
+        // Resolve the startup workspace against the durable owner scope. The
+        // gateway may expose a distinct sender identity, but the base runtime
+        // workspace stays owner-scoped and per-user gateway workspaces are
+        // handled separately by WorkspacePool.
+        let workspace = WorkspaceConfig::resolve(&owner_id)?;

        Ok(Self {
            owner_id: owner_id.clone(),
@@ -195,6 +195,20 @@ impl ContextManager {
            .collect()
    }

+    /// Count jobs consuming a parallel execution slot for a specific user.
+    ///
+    /// Uses `is_parallel_blocking()` (Pending/InProgress/Stuck) rather than
+    /// `is_active()`, so Completed/Submitted jobs don't count against the
+    /// per-user concurrency limit.
+    pub async fn parallel_blocking_count_for(&self, user_id: &str) -> usize {
+        self.contexts
+            .read()
+            .await
+            .iter()
+            .filter(|(_, c)| c.user_id == user_id && c.state.is_parallel_blocking())
+            .count()
+    }
+
    /// List all job IDs for a specific user.
    pub async fn all_jobs_for(&self, user_id: &str) -> Vec<Uuid> {
        self.contexts
@@ -192,6 +192,9 @@ pub struct JobContext {
    /// but subsequent tools (e.g., `json`) may need the full output. This
    /// stash stores the complete, unsanitized output so tools can reference
    /// previous results by ID via `$tool_call_id` parameter syntax.
+    ///
+    /// Also used for cross-tool implicit state (keys prefixed with `__`) such
+    /// as `__routine_last_name` for fallback recovery in routine tool chains.
    #[serde(skip)]
    pub tool_output_stash: Arc<tokio::sync::RwLock<HashMap<String, String>>>,
    /// User's preferred timezone (IANA name, e.g. "America/New_York"). Defaults to "UTC".
@@ -12,11 +12,11 @@ mod routines;
 mod sandbox;
 mod settings;
 mod tool_failures;
+mod users;
 mod workspace;

 use std::path::Path;
 use std::sync::Arc;
-use std::sync::atomic::{AtomicBool, Ordering};

 use async_trait::async_trait;
 use chrono::{DateTime, NaiveDateTime, Utc};
@@ -33,8 +33,6 @@ use crate::workspace::MemoryDocument;

 use crate::db::libsql_migrations;

-static NAIVE_TIMESTAMP_LOGGED: AtomicBool = AtomicBool::new(false);
-
 /// Explicit column list for routines table (matches positional access in `row_to_routine_libsql`).
 pub(crate) const ROUTINE_COLUMNS: &str = "\
    id, name, description, user_id, enabled, \
@@ -166,13 +164,11 @@ impl LibSqlBackend {
 ///
 /// Returns an error if none of the formats match.
 pub(crate) fn parse_timestamp(s: &str) -> Result<DateTime<Utc>, String> {
-    let log_naive_timestamp_once = || {
-        if !NAIVE_TIMESTAMP_LOGGED.swap(true, Ordering::Relaxed) {
-            tracing::debug!(
-                timestamp = %s,
-                "parsed naive timestamp without timezone; assuming UTC for backward compatibility"
-            );
-        }
+    let log_naive_timestamp = || {
+        tracing::warn!(
+            timestamp = %s,
+            "parsed naive timestamp, assuming UTC — consider migrating to RFC 3339"
+        );
    };

    // RFC 3339 (our canonical write format)
@@ -181,12 +177,12 @@ pub(crate) fn parse_timestamp(s: &str) -> Result<DateTime<Utc>, String> {
    }
    // Naive with fractional seconds (legacy or SQLite datetime() output)
    if let Ok(ndt) = NaiveDateTime::parse_from_str(s, "%Y-%m-%d %H:%M:%S%.f") {
-        log_naive_timestamp_once();
+        log_naive_timestamp();
        return Ok(ndt.and_utc());
    }
    // Naive without fractional seconds (legacy format)
    if let Ok(ndt) = NaiveDateTime::parse_from_str(s, "%Y-%m-%d %H:%M:%S") {
-        log_naive_timestamp_once();
+        log_naive_timestamp();
        return Ok(ndt.and_utc());
    }
    Err(format!("unparseable timestamp: {:?}", s))
@@ -438,7 +434,7 @@ mod tests {
    use chrono::{TimeZone, Utc};

    use crate::db::Database;
-    use crate::db::libsql::{LibSqlBackend, normalize_notify_user, parse_timestamp};
+    use crate::db::libsql::{LibSqlBackend, fmt_ts, normalize_notify_user, parse_timestamp};

    #[test]
    fn test_normalize_notify_user_treats_legacy_default_as_missing() {
@@ -467,6 +463,15 @@ mod tests {
        assert_eq!(naive_without_millis, expected);
    }

+    #[test]
+    fn test_fmt_ts_roundtrips_through_parse_timestamp() {
+        let original = Utc.with_ymd_and_hms(2026, 6, 15, 8, 30, 45).unwrap()
+            + chrono::Duration::milliseconds(123);
+        let formatted = fmt_ts(&original);
+        let parsed = parse_timestamp(&formatted).unwrap();
+        assert_eq!(parsed, original);
+    }
+
    #[tokio::test]
    async fn test_libsql_now_format_is_rfc3339_and_parseable() {
        let backend = LibSqlBackend::new_memory().await.unwrap();
@@ -462,6 +462,56 @@ impl RoutineStore for LibSqlBackend {
        Ok(counts)
    }

+    async fn batch_get_last_run_status(
+        &self,
+        routine_ids: &[Uuid],
+    ) -> Result<HashMap<Uuid, RunStatus>, DatabaseError> {
+        if routine_ids.is_empty() {
+            return Ok(HashMap::new());
+        }
+
+        let conn = self.connect().await?;
+
+        // SQLite doesn't support ANY($1), so we query all latest runs and filter in memory.
+        // Uses a subquery to pick only the most recent run per routine.
+        let mut rows = conn
+            .query(
+                "SELECT routine_id, status FROM routine_runs r1
+                 WHERE started_at = (
+                     SELECT MAX(started_at) FROM routine_runs r2
+                     WHERE r2.routine_id = r1.routine_id
+                 )
+                 GROUP BY routine_id",
+                params![],
+            )
+            .await
+            .map_err(|e| {
+                DatabaseError::Query(format!("Failed to batch get last run status: {}", e))
+            })?;
+
+        let routine_id_set: HashSet<Uuid> = routine_ids.iter().copied().collect();
+        let mut statuses = HashMap::new();
+
+        while let Some(row) = rows
+            .next()
+            .await
+            .map_err(|e| DatabaseError::Query(e.to_string()))?
+        {
+            let id_str: String = get_text(&row, 0);
+            let id = Uuid::parse_str(&id_str)
+                .map_err(|e| DatabaseError::Query(format!("Invalid routine UUID: {}", e)))?;
+
+            if routine_id_set.contains(&id) {
+                let status_str: String = get_text(&row, 1);
+                if let std::result::Result::Ok(status) = status_str.parse::<RunStatus>() {
+                    statuses.insert(id, status);
+                }
+            }
+        }
+
+        Ok(statuses)
+    }
+
    async fn link_routine_run_to_job(
        &self,
        run_id: Uuid,
@@ -480,10 +530,24 @@ impl RoutineStore for LibSqlBackend {
    async fn get_webhook_routine_by_path(
        &self,
        path: &str,
+        user_id: Option<&str>,
    ) -> Result<Option<Routine>, DatabaseError> {
        let conn = self.connect().await?;
-        let mut rows = conn
-            .query(
+        let mut rows = if let Some(uid) = user_id {
+            conn.query(
+                &format!(
+                    "SELECT {} FROM routines WHERE enabled = 1 AND trigger_type = 'webhook' \
+                     AND user_id = ?2 \
+                     AND (json_extract(trigger_config, '$.path') = ?1 \
+                     OR (json_extract(trigger_config, '$.path') IS NULL AND CAST(id AS TEXT) = ?1))",
+                    ROUTINE_COLUMNS
+                ),
+                params![path, uid],
+            )
+            .await
+            .map_err(|e| DatabaseError::Query(e.to_string()))?
+        } else {
+            conn.query(
                &format!(
                    "SELECT {} FROM routines WHERE enabled = 1 AND trigger_type = 'webhook' \
                     AND (json_extract(trigger_config, '$.path') = ?1 \
@@ -493,7 +557,8 @@ impl RoutineStore for LibSqlBackend {
                params![path],
            )
            .await
-            .map_err(|e| DatabaseError::Query(e.to_string()))?;
+            .map_err(|e| DatabaseError::Query(e.to_string()))?
+        };

        match rows
            .next()
@@ -579,6 +579,36 @@ INSERT OR IGNORE INTO leak_detection_patterns (id, name, pattern, severity, acti
    ('550e8400-e29b-41d4-a716-446655440011', 'mailchimp_api_key', '[a-f0-9]{32}-us[0-9]{1,2}', 'medium', 'block', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
    ('550e8400-e29b-41d4-a716-446655440012', 'high_entropy_hex', '(?<![a-fA-F0-9])[a-fA-F0-9]{64}(?![a-fA-F0-9])', 'medium', 'warn', 1, strftime('%Y-%m-%dT%H:%M:%fZ', 'now'));

+
+-- ==================== User management (V14) ====================
+
+CREATE TABLE IF NOT EXISTS users (
+    id TEXT PRIMARY KEY,
+    email TEXT UNIQUE,
+    display_name TEXT NOT NULL,
+    status TEXT NOT NULL DEFAULT 'active',
+    role TEXT NOT NULL DEFAULT 'member',
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    updated_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    last_login_at TEXT,
+    created_by TEXT REFERENCES users(id) ON DELETE SET NULL,
+    metadata TEXT NOT NULL DEFAULT '{}'
+);
+
+CREATE TABLE IF NOT EXISTS api_tokens (
+    id TEXT PRIMARY KEY,
+    user_id TEXT NOT NULL REFERENCES users(id) ON DELETE CASCADE,
+    token_hash BLOB NOT NULL,
+    token_prefix TEXT NOT NULL,
+    name TEXT NOT NULL,
+    expires_at TEXT,
+    last_used_at TEXT,
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    revoked_at TEXT
+);
+CREATE INDEX IF NOT EXISTS idx_api_tokens_user ON api_tokens(user_id);
+CREATE INDEX IF NOT EXISTS idx_api_tokens_hash ON api_tokens(token_hash);
+
 "#;

 /// Incremental migrations applied after the base schema.
@@ -723,6 +753,38 @@ CREATE INDEX IF NOT EXISTS idx_routines_event_triggers
    WHERE enabled = 1 AND trigger_type IN ('event', 'system_event');

 PRAGMA foreign_keys=ON;
+"#,
+    ),
+    (
+        14,
+        "users",
+        r#"
+CREATE TABLE IF NOT EXISTS users (
+    id TEXT PRIMARY KEY,
+    email TEXT UNIQUE,
+    display_name TEXT NOT NULL,
+    status TEXT NOT NULL DEFAULT 'active',
+    role TEXT NOT NULL DEFAULT 'member',
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    updated_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    last_login_at TEXT,
+    created_by TEXT REFERENCES users(id) ON DELETE SET NULL,
+    metadata TEXT NOT NULL DEFAULT '{}'
+);
+
+CREATE TABLE IF NOT EXISTS api_tokens (
+    id TEXT PRIMARY KEY,
+    user_id TEXT NOT NULL REFERENCES users(id) ON DELETE CASCADE,
+    token_hash BLOB NOT NULL,
+    token_prefix TEXT NOT NULL,
+    name TEXT NOT NULL,
+    expires_at TEXT,
+    last_used_at TEXT,
+    created_at TEXT NOT NULL DEFAULT (strftime('%Y-%m-%dT%H:%M:%fZ', 'now')),
+    revoked_at TEXT
+);
+CREATE INDEX IF NOT EXISTS idx_api_tokens_user ON api_tokens(user_id);
+CREATE INDEX IF NOT EXISTS idx_api_tokens_hash ON api_tokens(token_hash);
 "#,
    ),
 ];
@@ -309,6 +309,43 @@ async fn validate_postgres(pool: &deadpool_postgres::Pool) -> Result<(), Databas
    Ok(())
 }

+// ==================== User management record types ====================
+
+/// A registered user.
+#[derive(Debug, Clone)]
+pub struct UserRecord {
+    /// User identifier (string, matches existing `user_id` throughout the codebase).
+    pub id: String,
+    pub email: Option<String>,
+    pub display_name: String,
+    /// `active`, `suspended`, or `deactivated`.
+    pub status: String,
+    /// `admin` or `member`.
+    pub role: String,
+    pub created_at: DateTime<Utc>,
+    pub updated_at: DateTime<Utc>,
+    pub last_login_at: Option<DateTime<Utc>>,
+    /// Who created/invited this user (nullable for bootstrap users).
+    pub created_by: Option<String>,
+    pub metadata: serde_json::Value,
+}
+
+/// An API token for authenticating requests (hash stored, never plaintext).
+#[derive(Debug, Clone)]
+pub struct ApiTokenRecord {
+    pub id: Uuid,
+    pub user_id: String,
+    /// Human label (e.g. "my-laptop", "ci-bot").
+    pub name: String,
+    /// First 8 hex chars of the plaintext token for display/identification.
+    pub token_prefix: String,
+    pub expires_at: Option<DateTime<Utc>>,
+    pub last_used_at: Option<DateTime<Utc>>,
+    pub created_at: DateTime<Utc>,
+    /// Soft-revoke timestamp. Non-null means revoked.
+    pub revoked_at: Option<DateTime<Utc>>,
+}
+
 // ==================== Sub-traits ====================
 //
 // Each sub-trait groups related persistence methods. The `Database` supertrait
@@ -528,6 +565,15 @@ pub trait RoutineStore: Send + Sync {
        &self,
        routine_ids: &[Uuid],
    ) -> Result<HashMap<Uuid, i64>, DatabaseError>;
+
+    /// Fetch the last run status for multiple routines in a single query.
+    /// Returns a map from routine_id to its most recent RunStatus.
+    /// Routines with no runs are omitted from the result.
+    async fn batch_get_last_run_status(
+        &self,
+        routine_ids: &[Uuid],
+    ) -> Result<HashMap<Uuid, RunStatus>, DatabaseError>;
+
    async fn link_routine_run_to_job(
        &self,
        run_id: Uuid,
@@ -536,6 +582,7 @@ pub trait RoutineStore: Send + Sync {
    async fn get_webhook_routine_by_path(
        &self,
        path: &str,
+        user_id: Option<&str>,
    ) -> Result<Option<Routine>, DatabaseError>;

    /// List routine runs that were dispatched as full_job but have not yet
@@ -751,6 +798,113 @@ pub trait WorkspaceStore: Send + Sync {
    }
 }

+#[async_trait]
+pub trait UserStore: Send + Sync {
+    // ---- Users ----
+
+    /// Create a new user record.
+    async fn create_user(&self, user: &UserRecord) -> Result<(), DatabaseError>;
+    /// Get a user by their string id.
+    async fn get_user(&self, id: &str) -> Result<Option<UserRecord>, DatabaseError>;
+    /// Get a user by email address.
+    async fn get_user_by_email(&self, email: &str) -> Result<Option<UserRecord>, DatabaseError>;
+    /// List users, optionally filtered by status.
+    async fn list_users(&self, status: Option<&str>) -> Result<Vec<UserRecord>, DatabaseError>;
+    /// Update a user's status (active/suspended/deactivated).
+    async fn update_user_status(&self, id: &str, status: &str) -> Result<(), DatabaseError>;
+    /// Update a user's role (admin/member).
+    async fn update_user_role(&self, id: &str, role: &str) -> Result<(), DatabaseError>;
+    /// Update a user's display name and metadata.
+    async fn update_user_profile(
+        &self,
+        id: &str,
+        display_name: &str,
+        metadata: &serde_json::Value,
+    ) -> Result<(), DatabaseError>;
+    /// Record a login timestamp.
+    async fn record_login(&self, id: &str) -> Result<(), DatabaseError>;
+
+    // ---- API Tokens ----
+
+    /// Create a new API token. The `token_hash` is SHA-256 of the plaintext.
+    async fn create_api_token(
+        &self,
+        user_id: &str,
+        name: &str,
+        token_hash: &[u8; 32],
+        token_prefix: &str,
+        expires_at: Option<DateTime<Utc>>,
+    ) -> Result<ApiTokenRecord, DatabaseError>;
+    /// List tokens for a user (never includes the hash).
+    async fn list_api_tokens(&self, user_id: &str) -> Result<Vec<ApiTokenRecord>, DatabaseError>;
+    /// Soft-revoke a token. Returns false if the token doesn't exist or doesn't belong to the user.
+    async fn revoke_api_token(&self, token_id: Uuid, user_id: &str) -> Result<bool, DatabaseError>;
+    /// Look up a token by hash, returning the token record and its owning user.
+    /// Only returns active (non-revoked, non-expired) tokens for active users.
+    async fn authenticate_token(
+        &self,
+        token_hash: &[u8; 32],
+    ) -> Result<Option<(ApiTokenRecord, UserRecord)>, DatabaseError>;
+    /// Update `last_used_at` for a token.
+    async fn record_token_usage(&self, token_id: Uuid) -> Result<(), DatabaseError>;
+
+    /// Check whether any user records exist (for first-run bootstrap detection).
+    async fn has_any_users(&self) -> Result<bool, DatabaseError>;
+
+    /// Delete a user and all their data across all user-scoped tables.
+    /// Returns false if the user doesn't exist.
+    async fn delete_user(&self, id: &str) -> Result<bool, DatabaseError>;
+
+    /// Get per-user LLM usage stats for a time period.
+    /// Aggregates from llm_calls via agent_jobs.user_id.
+    async fn user_usage_stats(
+        &self,
+        user_id: Option<&str>,
+        since: DateTime<Utc>,
+    ) -> Result<Vec<UserUsageStats>, DatabaseError>;
+
+    /// Lightweight per-user summary stats (job count, total cost, last active).
+    /// Used by the admin users list to show inline stats.
+    async fn user_summary_stats(
+        &self,
+        user_id: Option<&str>,
+    ) -> Result<Vec<UserSummaryStats>, DatabaseError>;
+
+    /// Create a user and their initial API token atomically.
+    /// If either operation fails, both are rolled back.
+    async fn create_user_with_token(
+        &self,
+        user: &UserRecord,
+        token_name: &str,
+        token_hash: &[u8; 32],
+        token_prefix: &str,
+        expires_at: Option<DateTime<Utc>>,
+    ) -> Result<ApiTokenRecord, DatabaseError>;
+}
+
+/// Per-user LLM usage statistics.
+#[derive(Debug, Clone)]
+pub struct UserUsageStats {
+    pub user_id: String,
+    pub model: String,
+    pub call_count: i64,
+    pub input_tokens: i64,
+    pub output_tokens: i64,
+    pub total_cost: Decimal,
+}
+
+/// Lightweight per-user summary for the admin users list.
+#[derive(Debug, Clone)]
+pub struct UserSummaryStats {
+    pub user_id: String,
+    /// Total agent jobs created by this user.
+    pub job_count: i64,
+    /// Total LLM spend across all jobs (all-time).
+    pub total_cost: Decimal,
+    /// Most recent activity (latest job or LLM call timestamp).
+    pub last_active_at: Option<DateTime<Utc>>,
+}
+
 /// Backend-agnostic database supertrait.
 ///
 /// Combines all sub-traits into one. Existing `Arc<dyn Database>` consumers
@@ -764,6 +918,7 @@ pub trait Database:
    + ToolFailureStore
    + SettingsStore
    + WorkspaceStore
+    + UserStore
    + Send
    + Sync
 {
@@ -16,8 +16,8 @@ use crate::agent::routine::{Routine, RoutineRun, RunStatus};
 use crate::config::DatabaseConfig;
 use crate::context::{ActionRecord, JobContext, JobState};
 use crate::db::{
-    ConversationStore, Database, JobStore, RoutineStore, SandboxStore, SettingsStore,
-    ToolFailureStore, WorkspaceStore,
+    ApiTokenRecord, ConversationStore, Database, JobStore, RoutineStore, SandboxStore,
+    SettingsStore, ToolFailureStore, UserRecord, UserStore, WorkspaceStore,
 };
 use crate::error::{DatabaseError, WorkspaceError};
 use crate::history::{
@@ -510,6 +510,14 @@ impl RoutineStore for PgBackend {
            .await
    }

+    async fn batch_get_last_run_status(
+        &self,
+        routine_ids: &[Uuid],
+    ) -> Result<std::collections::HashMap<Uuid, crate::agent::routine::RunStatus>, DatabaseError>
+    {
+        self.store.batch_get_last_run_status(routine_ids).await
+    }
+
    async fn link_routine_run_to_job(
        &self,
        run_id: Uuid,
@@ -521,8 +529,9 @@ impl RoutineStore for PgBackend {
    async fn get_webhook_routine_by_path(
        &self,
        path: &str,
+        user_id: Option<&str>,
    ) -> Result<Option<Routine>, DatabaseError> {
-        self.store.get_webhook_routine_by_path(path).await
+        self.store.get_webhook_routine_by_path(path, user_id).await
    }

    async fn list_dispatched_routine_runs(&self) -> Result<Vec<RoutineRun>, DatabaseError> {
@@ -777,3 +786,115 @@ impl WorkspaceStore for PgBackend {
            .await
    }
 }
+
+// ==================== UserStore ====================
+
+#[async_trait]
+impl UserStore for PgBackend {
+    async fn create_user(&self, user: &UserRecord) -> Result<(), DatabaseError> {
+        self.store.create_user(user).await
+    }
+
+    async fn get_user(&self, id: &str) -> Result<Option<UserRecord>, DatabaseError> {
+        self.store.get_user(id).await
+    }
+
+    async fn get_user_by_email(&self, email: &str) -> Result<Option<UserRecord>, DatabaseError> {
+        self.store.get_user_by_email(email).await
+    }
+
+    async fn list_users(&self, status: Option<&str>) -> Result<Vec<UserRecord>, DatabaseError> {
+        self.store.list_users(status).await
+    }
+
+    async fn update_user_status(&self, id: &str, status: &str) -> Result<(), DatabaseError> {
+        self.store.update_user_status(id, status).await
+    }
+
+    async fn update_user_role(&self, id: &str, role: &str) -> Result<(), DatabaseError> {
+        self.store.update_user_role(id, role).await
+    }
+
+    async fn update_user_profile(
+        &self,
+        id: &str,
+        display_name: &str,
+        metadata: &serde_json::Value,
+    ) -> Result<(), DatabaseError> {
+        self.store
+            .update_user_profile(id, display_name, metadata)
+            .await
+    }
+
+    async fn record_login(&self, id: &str) -> Result<(), DatabaseError> {
+        self.store.record_login(id).await
+    }
+
+    async fn create_api_token(
+        &self,
+        user_id: &str,
+        name: &str,
+        token_hash: &[u8; 32],
+        token_prefix: &str,
+        expires_at: Option<DateTime<Utc>>,
+    ) -> Result<ApiTokenRecord, DatabaseError> {
+        self.store
+            .create_api_token(user_id, name, token_hash, token_prefix, expires_at)
+            .await
+    }
+
+    async fn list_api_tokens(&self, user_id: &str) -> Result<Vec<ApiTokenRecord>, DatabaseError> {
+        self.store.list_api_tokens(user_id).await
+    }
+
+    async fn revoke_api_token(&self, token_id: Uuid, user_id: &str) -> Result<bool, DatabaseError> {
+        self.store.revoke_api_token(token_id, user_id).await
+    }
+
+    async fn authenticate_token(
+        &self,
+        token_hash: &[u8; 32],
+    ) -> Result<Option<(ApiTokenRecord, UserRecord)>, DatabaseError> {
+        self.store.authenticate_token(token_hash).await
+    }
+
+    async fn record_token_usage(&self, token_id: Uuid) -> Result<(), DatabaseError> {
+        self.store.record_token_usage(token_id).await
+    }
+
+    async fn has_any_users(&self) -> Result<bool, DatabaseError> {
+        self.store.has_any_users().await
+    }
+
+    async fn delete_user(&self, id: &str) -> Result<bool, DatabaseError> {
+        self.store.delete_user(id).await
+    }
+
+    async fn user_usage_stats(
+        &self,
+        user_id: Option<&str>,
+        since: DateTime<Utc>,
+    ) -> Result<Vec<crate::db::UserUsageStats>, DatabaseError> {
+        self.store.user_usage_stats(user_id, since).await
+    }
+
+    async fn user_summary_stats(
+        &self,
+        user_id: Option<&str>,
+    ) -> Result<Vec<crate::db::UserSummaryStats>, DatabaseError> {
+        self.store.user_summary_stats(user_id).await
+    }
+
+    async fn create_user_with_token(
+        &self,
+        user: &UserRecord,
+        token_name: &str,
+        token_hash: &[u8; 32],
+        token_prefix: &str,
+        expires_at: Option<DateTime<Utc>>,
+    ) -> Result<ApiTokenRecord, DatabaseError> {
+        self.store
+            .create_user_with_token(user, token_name, token_hash, token_prefix, expires_at)
+            .await
+    }
+}
@@ -2,7 +2,8 @@
 //!
 //! Builds a [`deadpool_postgres::Pool`] with the appropriate TLS connector
 //! based on the configured [`SslMode`].  Uses `rustls` with system root
-//! certificates — the same TLS stack that `reqwest` already uses for HTTP.
+//! certificates, falling back to Mozilla's bundled roots via `webpki-roots`
+//! when the system store is empty (common in minimal container images).

 use deadpool_postgres::{Pool, Runtime};
 use thiserror::Error;
@@ -19,9 +20,15 @@ pub enum CreatePoolError {
    TlsConfig(#[from] rustls::Error),
 }

-/// Build a rustls-based TLS connector using the platform's root certificate store.
+/// Build a rustls-based TLS connector.
+///
+/// Tries the platform's native certificate store first. If that yields zero
+/// certificates (slim container images, missing ca-certificates package),
+/// falls back to Mozilla's root certificates bundled via `webpki-roots`.
 fn make_rustls_connector() -> Result<MakeRustlsConnect, rustls::Error> {
    let mut root_store = rustls::RootCertStore::empty();
+
+    // Try native certs first.
    let native = rustls_native_certs::load_native_certs();
    for e in &native.errors {
        tracing::warn!("error loading system root certs: {e}");
@@ -31,11 +38,14 @@ fn make_rustls_connector() -> Result<MakeRustlsConnect, rustls::Error> {
            tracing::warn!("skipping invalid system root cert: {e}");
        }
    }
+
+    // Fall back to bundled Mozilla roots when the system store is empty.
    if root_store.is_empty() {
-        tracing::error!("no system root certificates found -- TLS connections will fail");
+        tracing::info!("no system root certificates found, using bundled Mozilla roots");
+        root_store.extend(webpki_roots::TLS_SERVER_ROOTS.iter().cloned());
    }
-    // `--all-features` brings in both aws-lc-rs and ring-backed rustls providers.
-    // Pick the same ring provider reqwest already uses so postgres TLS setup stays deterministic.
+
+    // Pick the ring crypto provider (same one reqwest uses).
    let config = rustls::ClientConfig::builder_with_provider(
        rustls::crypto::ring::default_provider().into(),
    )
@@ -48,7 +58,7 @@ fn make_rustls_connector() -> Result<MakeRustlsConnect, rustls::Error> {
 /// Create a [`deadpool_postgres::Pool`] with the appropriate TLS connector.
 ///
 /// - `Disable` → plain TCP (no TLS)
-/// - `Prefer` / `Require` → rustls with system root certificates
+/// - `Prefer` / `Require` → rustls with system or bundled root certificates
 ///
 /// **Note:** `Prefer` and `Require` currently behave identically — both
 /// provide a TLS connector and will fail if the server rejects the TLS
@@ -81,7 +91,6 @@ mod tests {
    fn create_pool_disable_mode() {
        let mut config = deadpool_postgres::Config::new();
        config.url = Some("postgres://localhost/test".to_string());
-        // Should succeed — pool is created lazily, no actual connection needed.
        let pool = create_pool(&config, SslMode::Disable);
        assert!(pool.is_ok());
    }
@@ -395,16 +395,49 @@ pub enum RoutineError {
    Database { reason: String },

    #[error("LLM call failed: {reason}")]
-    LlmFailed { reason: String },
+    LlmFailed {
+        reason: String,
+        /// Partial token count consumed before the failure (if any).
+        /// Used to accumulate usage across retry attempts.
+        partial_tokens: Option<i32>,
+        /// Whether the underlying LLM error was classified as retryable.
+        /// Set at the `LlmError` → `RoutineError` conversion site using
+        /// `crate::llm::retry::is_retryable()`, avoiding fragile substring
+        /// matching on the stringified reason.
+        retryable: bool,
+    },

    #[error("Failed to dispatch full job: {reason}")]
    JobDispatchFailed { reason: String },

    #[error("LLM returned empty content")]
-    EmptyResponse,
+    EmptyResponse {
+        /// Tokens consumed by the call that produced the empty response.
+        partial_tokens: Option<i32>,
+    },

    #[error("LLM response truncated (finish_reason=length) with no content")]
-    TruncatedResponse,
+    TruncatedResponse {
+        /// Tokens consumed by the call that produced the truncated response.
+        partial_tokens: Option<i32>,
+    },
+}
+
+impl RoutineError {
+    /// Whether this error is transient and worth retrying with backoff.
+    ///
+    /// Retryable: LLM failures where the underlying `LlmError` was classified
+    /// as retryable by `crate::llm::retry::is_retryable()`, empty responses,
+    /// and truncated responses.
+    /// Non-retryable: configuration errors, authorization, resource limits,
+    /// DB errors, and LLM failures caused by auth/content-policy/context-length.
+    pub fn is_retryable(&self) -> bool {
+        match self {
+            RoutineError::LlmFailed { retryable, .. } => *retryable,
+            RoutineError::EmptyResponse { .. } | RoutineError::TruncatedResponse { .. } => true,
+            _ => false,
+        }
+    }
 }

 /// Result type alias for the agent.
@@ -514,6 +547,99 @@ mod tests {
        assert!(msg.contains("bad format"), "Should mention reason: {msg}");
    }

+    #[test]
+    fn routine_error_retryable_classification() {
+        // Transient errors should be retryable
+        assert!(
+            RoutineError::LlmFailed {
+                reason: "timeout".into(),
+                partial_tokens: None,
+                retryable: true,
+            }
+            .is_retryable()
+        );
+        // Non-retryable LLM error
+        assert!(
+            !RoutineError::LlmFailed {
+                reason: "timeout".into(),
+                partial_tokens: None,
+                retryable: false,
+            }
+            .is_retryable()
+        );
+        assert!(
+            RoutineError::EmptyResponse {
+                partial_tokens: None
+            }
+            .is_retryable()
+        );
+        assert!(
+            RoutineError::TruncatedResponse {
+                partial_tokens: None
+            }
+            .is_retryable()
+        );
+
+        // Hard failures should NOT be retryable
+        assert!(
+            !RoutineError::Disabled {
+                name: "test".into()
+            }
+            .is_retryable()
+        );
+        assert!(
+            !RoutineError::JobDispatchFailed {
+                reason: "no docker".into()
+            }
+            .is_retryable()
+        );
+        assert!(
+            !RoutineError::Database {
+                reason: "conn refused".into()
+            }
+            .is_retryable()
+        );
+        assert!(!RoutineError::NotFound { id: Uuid::new_v4() }.is_retryable());
+        assert!(!RoutineError::NotAuthorized { id: Uuid::new_v4() }.is_retryable());
+        assert!(
+            !RoutineError::MaxConcurrent {
+                name: "test".into()
+            }
+            .is_retryable()
+        );
+        assert!(
+            !RoutineError::UnknownTriggerType {
+                trigger_type: "x".into()
+            }
+            .is_retryable()
+        );
+        assert!(
+            !RoutineError::UnknownActionType {
+                action_type: "x".into()
+            }
+            .is_retryable()
+        );
+        assert!(
+            !RoutineError::MissingField {
+                context: "c".into(),
+                field: "f".into()
+            }
+            .is_retryable()
+        );
+        assert!(
+            !RoutineError::InvalidCron {
+                reason: "bad".into()
+            }
+            .is_retryable()
+        );
+        assert!(
+            !RoutineError::UnknownRunStatus {
+                status: "bad".into()
+            }
+            .is_retryable()
+        );
+    }
+
    #[test]
    fn top_level_error_from_conversions() {
        let config_err = ConfigError::MissingEnvVar("TEST".to_string());
@@ -1162,15 +1162,25 @@ impl Store {
    pub async fn get_webhook_routine_by_path(
        &self,
        path: &str,
+        user_id: Option<&str>,
    ) -> Result<Option<Routine>, DatabaseError> {
        let conn = self.conn().await?;
-        let row = conn
-            .query_opt(
+        let row = if let Some(uid) = user_id {
+            conn.query_opt(
+                "SELECT * FROM routines WHERE enabled AND trigger_type = 'webhook' \
+                 AND user_id = $2 \
+                 AND (trigger_config->>'path' = $1 OR (trigger_config->>'path' IS NULL AND id::text = $1))",
+                &[&path, &uid],
+            )
+            .await?
+        } else {
+            conn.query_opt(
                "SELECT * FROM routines WHERE enabled AND trigger_type = 'webhook' \
                 AND (trigger_config->>'path' = $1 OR (trigger_config->>'path' IS NULL AND id::text = $1))",
                &[&path],
            )
-            .await?;
+            .await?
+        };
        row.as_ref().map(row_to_routine).transpose()
    }

@@ -1403,6 +1413,40 @@ impl Store {
        Ok(counts)
    }

+    /// Batch-load the most recent run status for multiple routines in a single query.
+    /// Uses a window function to pick only the latest run per routine.
+    #[cfg(feature = "postgres")]
+    pub async fn batch_get_last_run_status(
+        &self,
+        routine_ids: &[Uuid],
+    ) -> Result<HashMap<Uuid, RunStatus>, DatabaseError> {
+        if routine_ids.is_empty() {
+            return Ok(HashMap::new());
+        }
+
+        let conn = self.conn().await?;
+        let rows = conn
+            .query(
+                "SELECT DISTINCT ON (routine_id) routine_id, status
+                 FROM routine_runs
+                 WHERE routine_id = ANY($1)
+                 ORDER BY routine_id, started_at DESC",
+                &[&routine_ids],
+            )
+            .await?;
+
+        let mut statuses = HashMap::new();
+        for row in rows {
+            let id: Uuid = row.get("routine_id");
+            let status_str: String = row.get("status");
+            if let std::result::Result::Ok(status) = status_str.parse::<RunStatus>() {
+                statuses.insert(id, status);
+            }
+        }
+
+        Ok(statuses)
+    }
+
    /// Link a routine run to a dispatched job.
    pub async fn link_routine_run_to_job(
        &self,
@@ -2235,6 +2279,546 @@ impl Store {
    }
 }

+// ==================== Users / API Tokens / Invitations ====================
+
+#[cfg(feature = "postgres")]
+use crate::db::{ApiTokenRecord, UserRecord};
+
+#[cfg(feature = "postgres")]
+impl Store {
+    /// Create a new user record.
+    pub async fn create_user(&self, user: &UserRecord) -> Result<(), DatabaseError> {
+        let conn = self.conn().await?;
+        conn.execute(
+            r#"
+            INSERT INTO users (id, email, display_name, status, role, created_at, updated_at, last_login_at, created_by, metadata)
+            VALUES ($1, $2, $3, $4, $5, $6, $7, $8, $9, $10)
+            "#,
+            &[
+                &user.id,
+                &user.email,
+                &user.display_name,
+                &user.status,
+                &user.role,
+                &user.created_at,
+                &user.updated_at,
+                &user.last_login_at,
+                &user.created_by,
+                &user.metadata,
+            ],
+        )
+        .await?;
+        Ok(())
+    }
+
+    /// Get a user by their string id.
+    pub async fn get_user(&self, id: &str) -> Result<Option<UserRecord>, DatabaseError> {
+        let conn = self.conn().await?;
+        let row = conn
+            .query_opt("SELECT id, email, display_name, status, role, created_at, updated_at, last_login_at, created_by, metadata FROM users WHERE id = $1", &[&id])
+            .await?;
+        Ok(row.map(|r| row_to_user(&r)))
+    }
+
+    /// Get a user by email address.
+    pub async fn get_user_by_email(
+        &self,
+        email: &str,
+    ) -> Result<Option<UserRecord>, DatabaseError> {
+        let conn = self.conn().await?;
+        let row = conn
+            .query_opt("SELECT id, email, display_name, status, role, created_at, updated_at, last_login_at, created_by, metadata FROM users WHERE email = $1", &[&email])
+            .await?;
+        Ok(row.map(|r| row_to_user(&r)))
+    }
+
+    /// List users, optionally filtered by status.
+    pub async fn list_users(&self, status: Option<&str>) -> Result<Vec<UserRecord>, DatabaseError> {
+        let conn = self.conn().await?;
+        let rows = match status {
+            Some(s) => {
+                conn.query(
+                    "SELECT id, email, display_name, status, role, created_at, updated_at, last_login_at, created_by, metadata FROM users WHERE status = $1 ORDER BY created_at DESC",
+                    &[&s],
+                )
+                .await?
+            }
+            None => {
+                conn.query("SELECT id, email, display_name, status, role, created_at, updated_at, last_login_at, created_by, metadata FROM users ORDER BY created_at DESC", &[])
+                    .await?
+            }
+        };
+        Ok(rows.iter().map(row_to_user).collect())
+    }
+
+    /// Update a user's status.
+    pub async fn update_user_status(&self, id: &str, status: &str) -> Result<(), DatabaseError> {
+        let conn = self.conn().await?;
+        conn.execute(
+            "UPDATE users SET status = $1, updated_at = NOW() WHERE id = $2",
+            &[&status, &id],
+        )
+        .await?;
+        Ok(())
+    }
+
+    /// Update a user's role (admin/member).
+    pub async fn update_user_role(&self, id: &str, role: &str) -> Result<(), DatabaseError> {
+        let conn = self.conn().await?;
+        conn.execute(
+            "UPDATE users SET role = $1, updated_at = NOW() WHERE id = $2",
+            &[&role, &id],
+        )
+        .await?;
+        Ok(())
+    }
+
+    /// Update a user's display name and metadata.
+    pub async fn update_user_profile(
+        &self,
+        id: &str,
+        display_name: &str,
+        metadata: &serde_json::Value,
+    ) -> Result<(), DatabaseError> {
+        let conn = self.conn().await?;
+        conn.execute(
+            "UPDATE users SET display_name = $1, metadata = $2, updated_at = NOW() WHERE id = $3",
+            &[&display_name, metadata, &id],
+        )
+        .await?;
+        Ok(())
+    }
+
+    /// Record a login timestamp for a user.
+    pub async fn record_login(&self, id: &str) -> Result<(), DatabaseError> {
+        let conn = self.conn().await?;
+        conn.execute(
+            "UPDATE users SET last_login_at = NOW(), updated_at = NOW() WHERE id = $1",
+            &[&id],
+        )
+        .await?;
+        Ok(())
+    }
+
+    /// Create a new API token.
+    pub async fn create_api_token(
+        &self,
+        user_id: &str,
+        name: &str,
+        token_hash: &[u8; 32],
+        token_prefix: &str,
+        expires_at: Option<DateTime<Utc>>,
+    ) -> Result<ApiTokenRecord, DatabaseError> {
+        let conn = self.conn().await?;
+        let id = Uuid::new_v4();
+        let now = Utc::now();
+        conn.execute(
+            r#"
+            INSERT INTO api_tokens (id, user_id, token_hash, token_prefix, name, expires_at, created_at)
+            VALUES ($1, $2, $3, $4, $5, $6, $7)
+            "#,
+            &[
+                &id,
+                &user_id,
+                &token_hash.as_slice(),
+                &token_prefix,
+                &name,
+                &expires_at,
+                &now,
+            ],
+        )
+        .await?;
+        Ok(ApiTokenRecord {
+            id,
+            user_id: user_id.to_string(),
+            name: name.to_string(),
+            token_prefix: token_prefix.to_string(),
+            expires_at,
+            last_used_at: None,
+            created_at: now,
+            revoked_at: None,
+        })
+    }
+
+    /// Create a user and their initial API token atomically in a single transaction.
+    pub async fn create_user_with_token(
+        &self,
+        user: &UserRecord,
+        token_name: &str,
+        token_hash: &[u8; 32],
+        token_prefix: &str,
+        expires_at: Option<DateTime<Utc>>,
+    ) -> Result<ApiTokenRecord, DatabaseError> {
+        let mut conn = self.conn().await?;
+        let tx = conn.transaction().await?;
+
+        tx.execute(
+            r#"
+            INSERT INTO users (id, email, display_name, status, role, created_at, updated_at, last_login_at, created_by, metadata)
+            VALUES ($1, $2, $3, $4, $5, $6, $7, $8, $9, $10)
+            "#,
+            &[
+                &user.id,
+                &user.email,
+                &user.display_name,
+                &user.status,
+                &user.role,
+                &user.created_at,
+                &user.updated_at,
+                &user.last_login_at,
+                &user.created_by,
+                &user.metadata,
+            ],
+        )
+        .await?;
+
+        let id = Uuid::new_v4();
+        let now = Utc::now();
+        tx.execute(
+            r#"
+            INSERT INTO api_tokens (id, user_id, token_hash, token_prefix, name, expires_at, created_at)
+            VALUES ($1, $2, $3, $4, $5, $6, $7)
+            "#,
+            &[
+                &id,
+                &user.id,
+                &token_hash.as_slice(),
+                &token_prefix,
+                &token_name,
+                &expires_at,
+                &now,
+            ],
+        )
+        .await?;
+
+        tx.commit().await?;
+
+        Ok(ApiTokenRecord {
+            id,
+            user_id: user.id.clone(),
+            name: token_name.to_string(),
+            token_prefix: token_prefix.to_string(),
+            expires_at,
+            last_used_at: None,
+            created_at: now,
+            revoked_at: None,
+        })
+    }
+
+    /// List tokens for a user.
+    pub async fn list_api_tokens(
+        &self,
+        user_id: &str,
+    ) -> Result<Vec<ApiTokenRecord>, DatabaseError> {
+        let conn = self.conn().await?;
+        let rows = conn
+            .query(
+                r#"
+                SELECT id, user_id, name, token_prefix, expires_at, last_used_at, created_at, revoked_at
+                FROM api_tokens
+                WHERE user_id = $1
+                ORDER BY created_at DESC
+                "#,
+                &[&user_id],
+            )
+            .await?;
+        Ok(rows.iter().map(row_to_api_token).collect())
+    }
+
+    /// Soft-revoke a token. Returns false if the token doesn't exist or doesn't belong to the user.
+    pub async fn revoke_api_token(
+        &self,
+        token_id: Uuid,
+        user_id: &str,
+    ) -> Result<bool, DatabaseError> {
+        let conn = self.conn().await?;
+        let count = conn
+            .execute(
+                "UPDATE api_tokens SET revoked_at = NOW() WHERE id = $1 AND user_id = $2 AND revoked_at IS NULL",
+                &[&token_id, &user_id],
+            )
+            .await?;
+        Ok(count > 0)
+    }
+
+    /// Authenticate a token by hash. Returns the token record and its owning user
+    /// if the token is active (non-revoked, non-expired) and the user is active.
+    pub async fn authenticate_token(
+        &self,
+        token_hash: &[u8; 32],
+    ) -> Result<Option<(ApiTokenRecord, UserRecord)>, DatabaseError> {
+        let conn = self.conn().await?;
+        let row = conn
+            .query_opt(
+                r#"
+                SELECT t.id, t.user_id, t.name, t.token_prefix, t.expires_at, t.last_used_at, t.created_at, t.revoked_at,
+                       u.id as u_id, u.email, u.display_name, u.status, u.role, u.created_at as u_created_at, u.updated_at, u.last_login_at, u.created_by, u.metadata
+                FROM api_tokens t
+                JOIN users u ON t.user_id = u.id
+                WHERE t.token_hash = $1
+                  AND t.revoked_at IS NULL
+                  AND (t.expires_at IS NULL OR t.expires_at > NOW())
+                  AND u.status = 'active'
+                "#,
+                &[&token_hash.as_slice()],
+            )
+            .await?;
+        Ok(row.map(|r| {
+            let token = ApiTokenRecord {
+                id: r.get("id"),
+                user_id: r.get("user_id"),
+                name: r.get("name"),
+                token_prefix: r.get("token_prefix"),
+                expires_at: r.get("expires_at"),
+                last_used_at: r.get("last_used_at"),
+                created_at: r.get("created_at"),
+                revoked_at: r.get("revoked_at"),
+            };
+            let user = UserRecord {
+                id: r.get("u_id"),
+                email: r.get("email"),
+                display_name: r.get("display_name"),
+                status: r.get("status"),
+                role: r.get("role"),
+                created_at: r.get("u_created_at"),
+                updated_at: r.get("updated_at"),
+                last_login_at: r.get("last_login_at"),
+                created_by: r.get("created_by"),
+                metadata: r.get("metadata"),
+            };
+            (token, user)
+        }))
+    }
+
+    /// Update `last_used_at` for a token.
+    pub async fn record_token_usage(&self, token_id: Uuid) -> Result<(), DatabaseError> {
+        let conn = self.conn().await?;
+        conn.execute(
+            "UPDATE api_tokens SET last_used_at = NOW() WHERE id = $1",
+            &[&token_id],
+        )
+        .await?;
+        Ok(())
+    }
+
+    /// Check whether any user records exist.
+    pub async fn has_any_users(&self) -> Result<bool, DatabaseError> {
+        let conn = self.conn().await?;
+        let row = conn
+            .query_one(
+                "SELECT EXISTS(SELECT 1 FROM users LIMIT 1) as has_users",
+                &[],
+            )
+            .await?;
+        Ok(row.get("has_users"))
+    }
+
+    /// Delete a user and all their data across all user-scoped tables.
+    /// Returns false if the user doesn't exist.
+    pub async fn delete_user(&self, id: &str) -> Result<bool, DatabaseError> {
+        let mut conn = self.conn().await?;
+        let tx = conn
+            .transaction()
+            .await
+            .map_err(|e| DatabaseError::Query(e.to_string()))?;
+        // Delete from child tables first to avoid FK violations.
+        // job_events must come before agent_jobs (FK without CASCADE).
+        // agent_jobs cascades to job_actions, llm_calls, estimation_snapshots.
+        // conversations cascades to conversation_messages.
+        // memory_documents cascades to memory_chunks.
+        // routines cascades to routine_runs.
+        // api_tokens cascade automatically via FK on users.
+        for table in &[
+            "settings",
+            "heartbeat_state",
+            "tool_rate_limit_state",
+            "secret_usage_log",
+            "leak_detection_events",
+            "secrets",
+            "wasm_tools",
+            "routines",
+            "memory_documents",
+            "conversations",
+        ] {
+            tx.execute(&format!("DELETE FROM {table} WHERE user_id = $1"), &[&id])
+                .await
+                .map_err(|e| DatabaseError::Query(e.to_string()))?;
+        }
+        // job_events references agent_jobs(id) without CASCADE — delete via subquery.
+        tx.execute(
+            "DELETE FROM job_events WHERE job_id IN (SELECT id FROM agent_jobs WHERE user_id = $1)",
+            &[&id],
+        )
+        .await
+        .map_err(|e| DatabaseError::Query(e.to_string()))?;
+        tx.execute("DELETE FROM agent_jobs WHERE user_id = $1", &[&id])
+            .await
+            .map_err(|e| DatabaseError::Query(e.to_string()))?;
+        // Nullify self-referencing created_by before deleting the user
+        tx.execute(
+            "UPDATE users SET created_by = NULL WHERE created_by = $1",
+            &[&id],
+        )
+        .await
+        .map_err(|e| DatabaseError::Query(e.to_string()))?;
+        // api_tokens cascade automatically via FK
+        let result = tx
+            .execute("DELETE FROM users WHERE id = $1", &[&id])
+            .await
+            .map_err(|e| DatabaseError::Query(e.to_string()))?;
+        tx.commit()
+            .await
+            .map_err(|e| DatabaseError::Query(e.to_string()))?;
+        Ok(result > 0)
+    }
+
+    /// Get per-user LLM usage stats for a time period.
+    /// Aggregates from llm_calls via agent_jobs.user_id.
+    pub async fn user_usage_stats(
+        &self,
+        user_id: Option<&str>,
+        since: DateTime<Utc>,
+    ) -> Result<Vec<crate::db::UserUsageStats>, DatabaseError> {
+        let conn = self.conn().await?;
+        let rows = if let Some(uid) = user_id {
+            conn.query(
+                r#"
+                SELECT COALESCE(j.user_id, c.user_id) as user_id,
+                       l.model, COUNT(*) as call_count,
+                       COALESCE(SUM(l.input_tokens), 0) as input_tokens,
+                       COALESCE(SUM(l.output_tokens), 0) as output_tokens,
+                       COALESCE(SUM(l.cost), 0) as total_cost
+                FROM llm_calls l
+                LEFT JOIN agent_jobs j ON l.job_id = j.id
+                LEFT JOIN conversations c ON l.conversation_id = c.id
+                WHERE l.created_at >= $1
+                  AND COALESCE(j.user_id, c.user_id) = $2
+                GROUP BY COALESCE(j.user_id, c.user_id), l.model
+                ORDER BY total_cost DESC
+                "#,
+                &[&since, &uid],
+            )
+            .await?
+        } else {
+            conn.query(
+                r#"
+                SELECT COALESCE(j.user_id, c.user_id) as user_id,
+                       l.model, COUNT(*) as call_count,
+                       COALESCE(SUM(l.input_tokens), 0) as input_tokens,
+                       COALESCE(SUM(l.output_tokens), 0) as output_tokens,
+                       COALESCE(SUM(l.cost), 0) as total_cost
+                FROM llm_calls l
+                LEFT JOIN agent_jobs j ON l.job_id = j.id
+                LEFT JOIN conversations c ON l.conversation_id = c.id
+                WHERE l.created_at >= $1
+                GROUP BY COALESCE(j.user_id, c.user_id), l.model
+                ORDER BY total_cost DESC
+                "#,
+                &[&since],
+            )
+            .await?
+        };
+        let mut stats = Vec::with_capacity(rows.len());
+        for row in &rows {
+            stats.push(crate::db::UserUsageStats {
+                user_id: row.get("user_id"),
+                model: row.get("model"),
+                call_count: row.get("call_count"),
+                input_tokens: row.get("input_tokens"),
+                output_tokens: row.get("output_tokens"),
+                total_cost: row.get("total_cost"),
+            });
+        }
+        Ok(stats)
+    }
+
+    /// Lightweight per-user summary stats (job count, total cost, last active).
+    ///
+    /// Aggregates from `llm_calls`, resolving user_id via either `agent_jobs`
+    /// (for background job calls) or `conversations` (for chat calls where
+    /// `job_id` is NULL).
+    pub async fn user_summary_stats(
+        &self,
+        user_id: Option<&str>,
+    ) -> Result<Vec<crate::db::UserSummaryStats>, DatabaseError> {
+        let conn = self.conn().await?;
+        let rows = if let Some(uid) = user_id {
+            conn.query(
+                r#"
+                SELECT
+                    COALESCE(j.user_id, c.user_id) AS user_id,
+                    COUNT(DISTINCT j.id) AS job_count,
+                    COALESCE(SUM(l.cost), 0) AS total_cost,
+                    MAX(l.created_at) AS last_active_at
+                FROM llm_calls l
+                LEFT JOIN agent_jobs j ON l.job_id = j.id
+                LEFT JOIN conversations c ON l.conversation_id = c.id
+                WHERE COALESCE(j.user_id, c.user_id) = $1
+                GROUP BY COALESCE(j.user_id, c.user_id)
+                "#,
+                &[&uid],
+            )
+            .await?
+        } else {
+            conn.query(
+                r#"
+                SELECT
+                    COALESCE(j.user_id, c.user_id) AS user_id,
+                    COUNT(DISTINCT j.id) AS job_count,
+                    COALESCE(SUM(l.cost), 0) AS total_cost,
+                    MAX(l.created_at) AS last_active_at
+                FROM llm_calls l
+                LEFT JOIN agent_jobs j ON l.job_id = j.id
+                LEFT JOIN conversations c ON l.conversation_id = c.id
+                GROUP BY COALESCE(j.user_id, c.user_id)
+                "#,
+                &[],
+            )
+            .await?
+        };
+        let mut stats = Vec::with_capacity(rows.len());
+        for row in &rows {
+            stats.push(crate::db::UserSummaryStats {
+                user_id: row.get("user_id"),
+                job_count: row.get("job_count"),
+                total_cost: row.get("total_cost"),
+                last_active_at: row.get("last_active_at"),
+            });
+        }
+        Ok(stats)
+    }
+}
+
+#[cfg(feature = "postgres")]
+fn row_to_user(row: &tokio_postgres::Row) -> UserRecord {
+    UserRecord {
+        id: row.get("id"),
+        email: row.get("email"),
+        display_name: row.get("display_name"),
+        status: row.get("status"),
+        role: row.get("role"),
+        created_at: row.get("created_at"),
+        updated_at: row.get("updated_at"),
+        last_login_at: row.get("last_login_at"),
+        created_by: row.get("created_by"),
+        metadata: row.get("metadata"),
+    }
+}
+
+#[cfg(feature = "postgres")]
+fn row_to_api_token(row: &tokio_postgres::Row) -> ApiTokenRecord {
+    ApiTokenRecord {
+        id: row.get("id"),
+        user_id: row.get("user_id"),
+        name: row.get("name"),
+        token_prefix: row.get("token_prefix"),
+        expires_at: row.get("expires_at"),
+        last_used_at: row.get("last_used_at"),
+        created_at: row.get("created_at"),
+        revoked_at: row.get("revoked_at"),
+    }
+}
+
 #[cfg(test)]
 mod tests {
    use super::*;
@@ -69,6 +69,7 @@ pub mod service;
 pub mod settings;
 pub mod setup;
 pub mod skills;
+pub mod tenant;
 pub mod timezone;
 pub mod tools;
 pub mod tracing_fmt;
@@ -575,6 +575,7 @@ fn extract_response_content(response: &AnthropicResponse) -> (Option<String>, Ve
                    id: id.clone(),
                    name: name.clone(),
                    arguments: input.clone(),
+                    reasoning: None,
                });
            }
        }
@@ -623,6 +624,7 @@ mod tests {
            id: "call_1".to_string(),
            name: "search".to_string(),
            arguments: serde_json::json!({"q": "test"}),
+            reasoning: None,
        }];
        let messages = vec![
            ChatMessage::user("Search for test"),
--- a/Show More
+++ b/Show More