Format prompt guidance assertions

Co-authored-by: Copilot <[email protected]>

.github/workflows/test.yml

@@ -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

CHANGELOG.md

@@ -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

Cargo.lock

@@ -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]]
@@ -3390,7 +3390,7 @@ dependencies = [
 
 [[package]]
 name = "ironclaw"
-version = "0.19.0"
+version = "0.22.0"
 dependencies = [
  "aes-gcm",
  "aho-corasick",
@@ -3496,7 +3496,7 @@ dependencies = [
 
 [[package]]
 name = "ironclaw_safety"
-version = "0.1.0"
+version = "0.2.0"
 dependencies = [
  "aho-corasick",
  "regex",
@@ -5481,7 +5481,7 @@ dependencies = [
  "errno",
  "libc",
  "linux-raw-sys 0.12.1",
- "windows-sys 0.52.0",
+ "windows-sys 0.59.0",
 ]
 
 [[package]]
@@ -6388,7 +6388,7 @@ dependencies = [
  "getrandom 0.4.2",
  "once_cell",
  "rustix 1.1.4",
- "windows-sys 0.52.0",
+ "windows-sys 0.59.0",
 ]
 
 [[package]]

Cargo.toml

@@ -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"
@@ -104,7 +104,7 @@ cron = "0.13"
 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"
 

crates/ironclaw_common/Cargo.toml

@@ -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

crates/ironclaw_safety/Cargo.toml

@@ -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

registry/channels/feishu.json

@@ -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",
+      "sha256": "a66ff0dafb67d2216d8161bb7e96e724a94acb0ab993b85d2782d30412f8fe94",
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.19.0/channel-feishu-0.1.1-wasm32-wasip2.tar.gz"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/channel-feishu-0.1.3-wasm32-wasip2.tar.gz"
     }
   },
   "auth_summary": {

registry/channels/telegram.json

@@ -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",
+      "url": "https://github.com/nearai/ironclaw/releases/download/v0.20.0/channel-telegram-0.2.5-wasm32-wasip2.tar.gz",
-      "sha256": "a7cb300ec1c946831cfceaa95c1dc8f30d0f42a3924f3cb5de8098821573f4b8"
+      "sha256": "1ef20a538f55b379e049356e4d6758006251846bc3365ceaa1c87eba8379a329"
     }
   },
   "auth_summary": {

registry/tools/github.json

@@ -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",
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-github-0.2.2-wasm32-wasip2.tar.gz",
-      "sha256": "92c530b3ad172e2372d819744b5233f1d8f65768e26eb5a6c213eba3ce1de758"
+      "sha256": "70b55af593193d8fa495c0f702ea23284d83a624124f8a5f7564916ec5032c3f"
     }
   },
   "auth_summary": {

registry/tools/gmail.json

@@ -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",
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-gmail-0.2.1-wasm32-wasip2.tar.gz",
-      "sha256": "ee9574e02e92bc1d481f1310eb88afd99ee52bf6971074ab33bd76bf99b34b1d"
+      "sha256": "79025b40ee70ce1120acc4320bae50da095d7afb0ef67bd56d99b064b72ea779"
     }
   },
   "auth_summary": {

registry/tools/google-calendar.json

@@ -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",
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-google-calendar-0.2.1-wasm32-wasip2.tar.gz",
-      "sha256": "2fa47150ea222e787c122182ad6f4dfa2ffaf5fe490d05e8de887a76445f8d2d"
+      "sha256": "86bcc075010b08f5ab2f98f504cec1c6c9e0ca144857d185cbecf72a11f504bf"
     }
   },
   "auth_summary": {

registry/tools/google-docs.json

@@ -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",
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-google-docs-0.2.1-wasm32-wasip2.tar.gz",
-      "sha256": "40e134a1c1564f832ca861c3396895d4e33ec67b99313fc1f97baf8d971423a9"
+      "sha256": "39d476029764949498a53a6a223f9952b5f4df151be7b8b19bf3fe4d401a57cd"
     }
   },
   "auth_summary": {

registry/tools/google-drive.json

@@ -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",
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-google-drive-0.2.1-wasm32-wasip2.tar.gz",
-      "sha256": "002a341a1d58125563a7c69561b26fbc2629b04ea723cade744102bdc0fbb71f"
+      "sha256": "6e9a700fab93865c852af718666af64c5b534ad6a419fb4b736e07740188f494"
     }
   },
   "auth_summary": {

registry/tools/google-sheets.json

@@ -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",
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-google-sheets-0.2.1-wasm32-wasip2.tar.gz",
-      "sha256": "8aa2c9d52f033edea3a6c2311b0ec694ccb6d0a54ef07e94d72bf8be1ce8009a"
+      "sha256": "1f8c381799a916be83263cac9d497d52946e21b1b588592a3a42ca94a73b7051"
     }
   },
   "auth_summary": {

registry/tools/google-slides.json

@@ -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",
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-google-slides-0.2.1-wasm32-wasip2.tar.gz",
-      "sha256": "e931a97d4fd0b0b938e464dc7c7f2be6ea6b4d1508f5ea3cd931d44db23f05f5"
+      "sha256": "e2528be5da02f1b8cfc8ee9b0cdd849516c53d412e2f75c6175b3bded7f512cb"
     }
   },
   "auth_summary": {

registry/tools/llm-context.json

@@ -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",
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-llm-context-0.1.1-wasm32-wasip2.tar.gz",
-      "sha256": "d9ced2b1226b879135891e0ee40e072c7c95412e1b2462925a23853e1f92497e"
+      "sha256": "9b19e2fd05dbbbe3c8bd55309a91db09124e8415eb0f767828b6e10b55771e63"
     }
   },
   "auth_summary": {

registry/tools/slack.json

@@ -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",
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-slack-0.2.1-wasm32-wasip2.tar.gz",
-      "sha256": "ccfb0415d7a04f9497726c712d15216de36e86f498b849101283c017f5ab4efb"
+      "sha256": "927519e5b7734beeb022d3b8bbd152e0e6b9f67c9452a8ad47809d3c4221a137"
     }
   },
   "auth_summary": {

registry/tools/telegram.json

@@ -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",
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-telegram-0.2.1-wasm32-wasip2.tar.gz",
-      "sha256": "c17065ca41fae5f2a7c43b36144686718cd310a2f22442313bb1aa82bbad0ae4"
+      "sha256": "1e57d0755fc9c7b3ec013d079f30168898b484a6919f9edd105f0cd80131c1cd"
     }
   },
   "auth_summary": {

registry/tools/web-search.json

@@ -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",
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-web-search-0.2.2-wasm32-wasip2.tar.gz",
-      "sha256": "bad275ca4ec314adea5241d6b92c44ccf9cebcbca8e30ba2493cc0bcb4b57218"
+      "sha256": "47382b50c1ea7525b20d59dc02fab04e336d018665826c2f24710bdf460779ae"
     }
   },
   "auth_summary": {

release-plz.toml

@@ -1,7 +1,2 @@
 [workspace]
 git_release_enable = false
-
-[[package]]
-name = "ironclaw_safety"
-publish = false
-release = false

src/agent/agent_loop.rs

@@ -13,9 +13,10 @@ use futures::StreamExt;
 use uuid::Uuid;
 
 use crate::agent::context_monitor::ContextMonitor;
-use crate::agent::heartbeat::spawn_heartbeat;
+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 +330,50 @@ 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.
+        let workspace = match &self.deps.workspace {
+            Some(ws) if ws.user_id() == user_id => Some(Arc::clone(ws)),
+            _ => self
+                .deps
+                .store
+                .as_ref()
+                .map(|db| Arc::new(Workspace::new_with_db(user_id, Arc::clone(db)))),
+        };
+
+        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 +459,8 @@ impl Agent {
             self.config.stuck_threshold,
             self.config.max_repair_attempts,
         );
-        if let Some(ref store) = self.deps.store {
+        if let Some(admin) = self.admin_store() {
-            self_repair = self_repair.with_store(Arc::clone(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()));
@@ -508,6 +567,7 @@ impl Agent {
                         .with_interval(std::time::Duration::from_secs(hb_config.interval_secs));
                     config.quiet_hours_start = hb_config.quiet_hours_start;
                     config.quiet_hours_end = hb_config.quiet_hours_end;
+                    config.multi_tenant = hb_config.multi_tenant;
                     config.timezone = hb_config
                         .timezone
                         .clone()
@@ -537,30 +597,52 @@ 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 targeted_ok = if let Some(ref channel) = notify_channel {
-                                && let Some(ref user) = notify_target
+                                let target = effective_user.as_deref().or(notify_target.as_deref());
-                            {
+                                if let Some(user) = target {
-                                channels
+                                    channels
-                                    .broadcast(channel, user, response.clone())
+                                        .broadcast(channel, user, response.clone())
-                                    .await
+                                        .await
-                                    .is_ok()
+                                        .is_ok()
+                                } else {
+                                    false
+                                }
                             } else {
                                 false
                             };
 
-                            if !targeted_ok && let Some(ref user) = notify_user {
+                            if !targeted_ok {
-                                let results = channels.broadcast_all(user, response).await;
+                                let fallback = effective_user.as_deref().or(notify_user.as_deref());
-                                for (ch, result) in results {
+                                if let Some(user) = fallback {
-                                    if let Err(e) = result {
+                                    let results = channels.broadcast_all(user, response).await;
-                                        tracing::warn!(
+                                    for (ch, result) in results {
-                                            "Failed to broadcast heartbeat to {}: {}",
+                                        if let Err(e) = result {
-                                            ch,
+                                            tracing::warn!(
-                                            e
+                                                "Failed to broadcast heartbeat to {}: {}",
-                                        );
+                                                ch,
+                                                e
+                                            );
+                                        }
                                     }
                                 }
                             }
@@ -573,14 +655,29 @@ impl Agent {
                         .map(|h| h.to_workspace_config())
                         .unwrap_or_default();
 
-                    Some(spawn_heartbeat(
+                    if config.multi_tenant {
-                        config,
+                        if let Some(admin) = self.admin_store() {
-                        hygiene,
+                            Some(spawn_multi_user_heartbeat(
-                        workspace.clone(),
+                                config,
-                        self.cheap_llm().clone(),
+                                hygiene,
-                        Some(notify_tx),
+                                self.cheap_llm().clone(),
-                        self.store().map(Arc::clone),
+                                Some(notify_tx),
-                    ))
+                                admin,
+                            ))
+                        } else {
+                            tracing::warn!("Multi-tenant heartbeat requires a database store");
+                            None
+                        }
+                    } else {
+                        Some(spawn_heartbeat(
+                            config,
+                            hygiene,
+                            workspace.clone(),
+                            self.cheap_llm().clone(),
+                            Some(notify_tx),
+                            self.admin_store(),
+                        ))
+                    }
                 } else {
                     tracing::warn!("Heartbeat enabled but no workspace available");
                     None
@@ -602,7 +699,7 @@ 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,
@@ -1140,9 +1237,14 @@ impl Agent {
             && let Submission::UserInput { ref content } = submission
             && let Some(engine) = self.routine_engine().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 = engine.check_event_triggers(message, content).await;
+            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,
@@ -1150,15 +1252,30 @@ 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;
+
+        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.
@@ -1225,7 +1342,13 @@ 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
@@ -1263,11 +1386,17 @@ impl Agent {
                         SubmissionResult::Error { message } => {
                             Ok(Some(format!("Error: {}", message)))
                         }
-                        _ => Ok(Some(String::new())),
+                        _ => {
+                            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,
@@ -1280,12 +1409,9 @@ 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())
+                self.process_job_status(&tenant, job_id.as_deref()).await
-                    .await
-            }
-            Submission::JobCancel { job_id } => {
-                self.process_job_cancel(&message.user_id, &job_id).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
@@ -1325,7 +1451,26 @@ 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 { .. } => {
@@ -1341,7 +1486,7 @@ 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;
@@ -1503,4 +1648,17 @@ 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
+    }
 }

src/agent/agentic_loop.rs

@@ -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,
         }
     }
 
@@ -622,4 +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"
+        );
+    }
 }

src/agent/commands.rs

@@ -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?
+                self.handle_check_status(tenant, 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?
             }
+            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());
                 }
 
@@ -155,7 +151,8 @@ 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;
@@ -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
@@ -221,11 +223,12 @@ 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() {
+        // 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) => {
@@ -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))),
         }
@@ -559,6 +566,7 @@ impl Agent {
         command: &str,
         args: &[String],
         channel: &str,
+        tenant: &crate::tenant::TenantCtx,
     ) -> Result<SubmissionResult, Error> {
         match command {
             "help" => Ok(SubmissionResult::response(concat!(
@@ -752,19 +760,32 @@ impl Agent {
                         }
                     }
 
-                    match self.llm().set_model(requested) {
+                    if self.config.multi_tenant {
-                        Ok(()) => {
+                        // Multi-tenant: only persist to per-user DB settings.
-                            // Persist the model choice so it survives restarts.
+                        // Do NOT call set_model() on the shared provider — that
-                            self.persist_selected_model(requested).await;
+                        // would change the default for all users. The per-request
-                            Ok(SubmissionResult::response(format!(
+                        // model_override in the dispatcher reads from the same
-                                "Switched model to: {}",
+                        // "selected_model" setting and applies it per-user.
-                                requested
+                        self.persist_selected_model(tenant, requested).await;
-                            )))
+                        Ok(SubmissionResult::response(format!(
+                            "Model preference set to: {} (per-user)",
+                            requested
+                        )))
+                    } else {
+                        match self.llm().set_model(requested) {
+                            Ok(()) => {
+                                // Persist the model choice so it survives restarts.
+                                self.persist_selected_model(tenant, requested).await;
+                                Ok(SubmissionResult::response(format!(
+                                    "Switched model to: {}",
+                                    requested
+                                )))
+                            }
+                            Err(e) => Ok(SubmissionResult::error(format!(
+                                "Failed to switch model: {}",
+                                e
+                            ))),
                         }
-                        Err(e) => Ok(SubmissionResult::error(format!(
-                            "Failed to switch model: {}",
-                            e
-                        ))),
                     }
                 }
             }
@@ -906,10 +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))),
@@ -921,23 +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.
+    /// In multi-tenant mode, only the per-user DB setting is written — global
-        if let Some(store) = self.store() {
+    /// .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
+            if let Err(e) = store.set_setting("selected_model", &value).await {
-                .set_setting(self.owner_id(), "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 || {

src/agent/cost_guard.rs

@@ -21,6 +21,9 @@ pub struct CostGuardConfig {
     pub max_cost_per_day_cents: Option<u64>,
     /// Maximum LLM calls per hour. None = unlimited.
     pub max_actions_per_hour: Option<u64>,
+    /// Maximum spend per user per day in cents. None = unlimited.
+    /// Applied independently per user alongside the global budget.
+    pub max_cost_per_user_per_day_cents: Option<u64>,
 }
 
 /// Error returned when a cost limit is exceeded.
@@ -30,6 +33,12 @@ pub enum CostLimitExceeded {
     DailyBudget { spent_cents: u64, limit_cents: u64 },
     /// Hourly action rate limit reached.
     HourlyRate { actions: u64, limit: u64 },
+    /// Per-user daily spending cap reached.
+    UserDailyBudget {
+        user_id: String,
+        spent_cents: u64,
+        limit_cents: u64,
+    },
 }
 
 impl std::fmt::Display for CostLimitExceeded {
@@ -49,6 +58,17 @@ impl std::fmt::Display for CostLimitExceeded {
                 "Hourly action limit exceeded: {} actions of {} allowed per hour",
                 actions, limit
             ),
+            Self::UserDailyBudget {
+                user_id,
+                spent_cents,
+                limit_cents,
+            } => write!(
+                f,
+                "User '{}' daily cost limit exceeded: spent ${:.2} of ${:.2} allowed",
+                user_id,
+                *spent_cents as f64 / 100.0,
+                *limit_cents as f64 / 100.0
+            ),
         }
     }
 }
@@ -78,6 +98,9 @@ pub struct CostGuard {
 
     /// Per-model token usage since startup.
     model_tokens: Mutex<HashMap<String, ModelTokens>>,
+
+    /// Per-user daily cost tracking. Each entry resets independently at midnight UTC.
+    per_user_daily_cost: Mutex<HashMap<String, DailyCost>>,
 }
 
 struct DailyCost {
@@ -97,6 +120,7 @@ impl CostGuard {
             action_window: Mutex::new(VecDeque::new()),
             budget_exceeded: AtomicBool::new(false),
             model_tokens: Mutex::new(HashMap::new()),
+            per_user_daily_cost: Mutex::new(HashMap::new()),
         }
     }
 
@@ -203,6 +227,11 @@ impl CostGuard {
                 daily.reset_date = today;
                 self.budget_exceeded.store(false, Ordering::Relaxed);
                 tracing::info!("Cost guard: daily counter reset for {}", today);
+
+                // Prune per-user entries from previous days to prevent
+                // unbounded HashMap growth in long-lived deployments.
+                let mut per_user = self.per_user_daily_cost.lock().await;
+                per_user.retain(|_, entry| entry.reset_date == today);
             }
             daily.total += cost;
 
@@ -248,6 +277,85 @@ impl CostGuard {
         cost
     }
 
+    /// Record an LLM call with per-user attribution.
+    ///
+    /// Delegates to `record_llm_call` for global tracking, then additionally
+    /// records the cost against the user's daily budget.
+    #[allow(clippy::too_many_arguments)]
+    pub async fn record_llm_call_for_user(
+        &self,
+        user_id: &str,
+        model: &str,
+        input_tokens: u32,
+        output_tokens: u32,
+        cache_read_input_tokens: u32,
+        cache_creation_input_tokens: u32,
+        cache_read_discount: Decimal,
+        cache_write_multiplier: Decimal,
+        cost_per_token: Option<(Decimal, Decimal)>,
+    ) -> Decimal {
+        let cost = self
+            .record_llm_call(
+                model,
+                input_tokens,
+                output_tokens,
+                cache_read_input_tokens,
+                cache_creation_input_tokens,
+                cache_read_discount,
+                cache_write_multiplier,
+                cost_per_token,
+            )
+            .await;
+
+        // Track per-user daily cost
+        {
+            let today = chrono::Utc::now().date_naive();
+            let mut per_user = self.per_user_daily_cost.lock().await;
+            let entry = per_user
+                .entry(user_id.to_string())
+                .or_insert_with(|| DailyCost {
+                    total: Decimal::ZERO,
+                    reset_date: today,
+                });
+            if today != entry.reset_date {
+                entry.total = Decimal::ZERO;
+                entry.reset_date = today;
+            }
+            entry.total += cost;
+        }
+
+        cost
+    }
+
+    /// Check whether the next action is allowed for a specific user.
+    ///
+    /// Checks the global limits first (via `check_allowed`), then additionally
+    /// checks the per-user daily budget if configured.
+    pub async fn check_allowed_for_user(&self, user_id: &str) -> Result<(), CostLimitExceeded> {
+        // Check global limits first
+        self.check_allowed().await?;
+
+        // Check per-user daily budget
+        if let Some(limit_cents) = self.config.max_cost_per_user_per_day_cents {
+            let today = chrono::Utc::now().date_naive();
+            let per_user = self.per_user_daily_cost.lock().await;
+            if let Some(entry) = per_user.get(user_id)
+                && entry.reset_date == today
+            {
+                let spent_cents = to_cents(entry.total);
+                if spent_cents >= limit_cents {
+                    return Err(CostLimitExceeded::UserDailyBudget {
+                        user_id: user_id.to_string(),
+                        spent_cents,
+                        limit_cents,
+                    });
+                }
+            }
+        }
+
+        Ok(())
+    }
+
     /// Current daily spend in USD (as Decimal).
     pub async fn daily_spend(&self) -> Decimal {
         let daily = self.daily_cost.lock().await;
@@ -259,6 +367,16 @@ impl CostGuard {
         }
     }
 
+    /// Current daily spend for a specific user in USD (as Decimal).
+    pub async fn daily_spend_for_user(&self, user_id: &str) -> Decimal {
+        let today = chrono::Utc::now().date_naive();
+        let per_user = self.per_user_daily_cost.lock().await;
+        match per_user.get(user_id) {
+            Some(entry) if entry.reset_date == today => entry.total,
+            _ => Decimal::ZERO,
+        }
+    }
+
     /// Number of actions in the current hourly window.
     pub async fn actions_this_hour(&self) -> u64 {
         let mut window = self.action_window.lock().await;
@@ -314,7 +432,7 @@ mod tests {
     async fn test_daily_budget_enforcement() {
         let guard = CostGuard::new(CostGuardConfig {
             max_cost_per_day_cents: Some(1), // $0.01 limit
-            max_actions_per_hour: None,
+            ..CostGuardConfig::default()
         });
 
         // First call allowed
@@ -350,8 +468,8 @@ mod tests {
     #[tokio::test]
     async fn test_hourly_rate_enforcement() {
         let guard = CostGuard::new(CostGuardConfig {
-            max_cost_per_day_cents: None,
             max_actions_per_hour: Some(3),
+            ..CostGuardConfig::default()
         });
 
         // First 3 actions allowed
@@ -633,8 +751,8 @@ mod tests {
         // A fresh CostGuard with rate limits should not panic even if
         // checked_sub returns None (simulating short uptime).
         let guard = CostGuard::new(CostGuardConfig {
-            max_cost_per_day_cents: None,
             max_actions_per_hour: Some(100),
+            ..CostGuardConfig::default()
         });
 
         // These must not panic regardless of system uptime
@@ -656,4 +774,119 @@ mod tests {
         let result = Instant::now().checked_sub(std::time::Duration::MAX);
         assert!(result.is_none());
     }
+
+    #[tokio::test]
+    async fn test_per_user_daily_budget_enforcement() {
+        let guard = CostGuard::new(CostGuardConfig {
+            max_cost_per_day_cents: None,
+            max_actions_per_hour: None,
+            max_cost_per_user_per_day_cents: Some(1), // $0.01 per user
+        });
+
+        // Both users initially allowed
+        assert!(guard.check_allowed_for_user("alice").await.is_ok());
+        assert!(guard.check_allowed_for_user("bob").await.is_ok());
+
+        // Alice makes an expensive call
+        guard
+            .record_llm_call_for_user(
+                "alice",
+                "gpt-4o",
+                10_000,
+                10_000,
+                0,
+                0,
+                Decimal::ONE,
+                Decimal::ONE,
+                None,
+            )
+            .await;
+
+        // Alice should be blocked, Bob should still be allowed
+        let result = guard.check_allowed_for_user("alice").await;
+        assert!(result.is_err());
+        match result.unwrap_err() {
+            CostLimitExceeded::UserDailyBudget {
+                user_id,
+                limit_cents,
+                ..
+            } => {
+                assert_eq!(user_id, "alice");
+                assert_eq!(limit_cents, 1);
+            }
+            other => panic!("Expected UserDailyBudget, got {:?}", other),
+        }
+        assert!(guard.check_allowed_for_user("bob").await.is_ok());
+    }
+
+    #[tokio::test]
+    async fn test_per_user_daily_spend_tracking() {
+        let guard = CostGuard::new(CostGuardConfig::default());
+
+        assert_eq!(guard.daily_spend_for_user("alice").await, Decimal::ZERO);
+        assert_eq!(guard.daily_spend_for_user("bob").await, Decimal::ZERO);
+
+        let cost = guard
+            .record_llm_call_for_user(
+                "alice",
+                "gpt-4o",
+                1000,
+                500,
+                0,
+                0,
+                Decimal::ONE,
+                Decimal::ONE,
+                None,
+            )
+            .await;
+
+        assert_eq!(guard.daily_spend_for_user("alice").await, cost);
+        assert_eq!(guard.daily_spend_for_user("bob").await, Decimal::ZERO);
+        // Global spend should also be tracked
+        assert_eq!(guard.daily_spend().await, cost);
+    }
+
+    #[tokio::test]
+    async fn test_per_user_budget_independent_of_global() {
+        let guard = CostGuard::new(CostGuardConfig {
+            max_cost_per_day_cents: Some(100_000), // $1000 global limit
+            max_actions_per_hour: None,
+            max_cost_per_user_per_day_cents: Some(1), // $0.01 per user
+        });
+
+        // User hits their personal limit
+        guard
+            .record_llm_call_for_user(
+                "alice",
+                "gpt-4o",
+                10_000,
+                10_000,
+                0,
+                0,
+                Decimal::ONE,
+                Decimal::ONE,
+                None,
+            )
+            .await;
+
+        // Alice blocked by per-user limit, not global
+        assert!(guard.check_allowed_for_user("alice").await.is_err());
+        // Global limit is far from reached
+        assert!(guard.check_allowed().await.is_ok());
+        // Bob is unaffected
+        assert!(guard.check_allowed_for_user("bob").await.is_ok());
+    }
+
+    #[test]
+    fn test_user_cost_limit_display() {
+        let limit = CostLimitExceeded::UserDailyBudget {
+            user_id: "alice".to_string(),
+            spent_cents: 150,
+            limit_cents: 100,
+        };
+        let msg = limit.to_string();
+        assert!(msg.contains("alice"));
+        assert!(msg.contains("$1.50"));
+        assert!(msg.contains("$1.00"));
+    }
 }

src/agent/dispatcher.rs

@@ -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 {
@@ -331,8 +341,8 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
         reason_ctx: &mut ReasoningContext,
         iteration: usize,
     ) -> Result<crate::llm::RespondOutput, Error> {
-        // Enforce cost guardrails before the LLM call
+        // Enforce cost guardrails before the LLM call (global + per-user)
-        if let Err(limit) = self.agent.cost_guard().check_allowed().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(),
@@ -340,6 +350,21 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
             .into());
         }
 
+        // 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 TenantScope).
+        if iteration == 0
+            && 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();
+            if !model.is_empty() {
+                reason_ctx.model_override = Some(model.to_string());
+            }
+        }
+
         let output = match reasoning.respond_with_tools(reason_ctx).await {
             Ok(output) => output,
             Err(crate::error::LlmError::ContextLengthExceeded { used, limit }) => {
@@ -374,13 +399,22 @@ impl<'a> LoopDelegate for ChatDelegate<'a> {
             Err(e) => return Err(e.into()),
         };
 
-        // Record cost and track token usage
+        // Record cost and track token usage (global + per-user).
-        let model_name = self.agent.llm().active_model_name();
+        // When a model override is active, use the override name for attribution
+        // and let CostGuard look up pricing via costs::model_cost() instead of
+        // using the default provider's cost_per_token (which reflects the wrong model).
+        let (model_name, cost_per_token) = if let Some(ref ovr) = reason_ctx.model_override {
+            (ovr.clone(), None)
+        } else {
+            (
+                self.agent.llm().active_model_name(),
+                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
+            .tenant
-            .cost_guard()
             .record_llm_call(
                 &model_name,
                 output.usage.input_tokens,
@@ -389,7 +423,7 @@ 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!(
@@ -1300,6 +1334,7 @@ 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(
@@ -1315,10 +1350,14 @@ mod tests {
                 allow_local_tools: false,
                 max_cost_per_day_cents: None,
                 max_actions_per_hour: None,
+                max_cost_per_user_per_day_cents: None,
                 max_tool_iterations: 50,
                 auto_approve_tools: false,
                 default_timezone: "UTC".to_string(),
                 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()),
@@ -2176,6 +2215,7 @@ 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(
@@ -2191,10 +2231,14 @@ mod tests {
                 allow_local_tools: false,
                 max_cost_per_day_cents: None,
                 max_actions_per_hour: None,
+                max_cost_per_user_per_day_cents: None,
                 max_tool_iterations,
                 auto_approve_tools: true,
                 default_timezone: "UTC".to_string(),
                 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()),
@@ -2229,13 +2273,14 @@ 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;
 
@@ -2297,6 +2342,7 @@ 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(
@@ -2312,10 +2358,14 @@ mod tests {
                     allow_local_tools: false,
                     max_cost_per_day_cents: None,
                     max_actions_per_hour: None,
+                    max_cost_per_user_per_day_cents: None,
                     max_tool_iterations: max_iter,
                     auto_approve_tools: true,
                     default_timezone: "UTC".to_string(),
                     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()),
@@ -2335,13 +2385,14 @@ 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;
 

src/agent/heartbeat.rs

@@ -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;
 
@@ -57,6 +57,9 @@ 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 instead of
+    /// running heartbeat for a single user. Requires a database store.
+    pub multi_tenant: bool,
 }
 
 impl Default for HeartbeatConfig {
@@ -71,6 +74,7 @@ impl Default for HeartbeatConfig {
             quiet_hours_start: None,
             quiet_hours_end: None,
             timezone: None,
+            multi_tenant: false,
         }
     }
 }
@@ -178,7 +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,
 }
 
@@ -207,8 +211,8 @@ impl HeartbeatRunner {
         self
     }
 
-    /// Set the database store for persistent heartbeat conversations.
+    /// Set the admin-scoped database store for persistent heartbeat conversations.
-    pub fn with_store(mut self, store: Arc<dyn Database>) -> Self {
+    pub fn with_store(mut self, store: AdminScope) -> Self {
         self.store = Some(store);
         self
     }
@@ -396,7 +400,7 @@ impl HeartbeatRunner {
     }
 
     /// Send a notification about heartbeat findings.
-    async fn send_notification(&self, message: &str) {
+    pub(crate) 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;
@@ -493,7 +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 {
@@ -508,6 +512,179 @@ 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
+/// 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(
+    config: HeartbeatConfig,
+    hygiene_config: HygieneConfig,
+    llm: Arc<dyn LlmProvider>,
+    response_tx: Option<mpsc::Sender<OutgoingResponse>>,
+    store: AdminScope,
+) -> tokio::task::JoinHandle<()> {
+    tokio::spawn(async move {
+        if !config.enabled {
+            tracing::info!("Multi-user heartbeat is disabled");
+            return;
+        }
+
+        let mut tick_interval = if config.fire_at.is_none() {
+            let mut iv = tokio::time::interval(config.interval);
+            iv.tick().await; // skip immediate tick
+            Some(iv)
+        } else {
+            None
+        };
+
+        // Track consecutive failures per user so we can disable heartbeat
+        // for persistently-failing users (same semantics as single-user mode).
+        let mut user_failures: std::collections::HashMap<String, u32> =
+            std::collections::HashMap::new();
+
+        tracing::info!("Starting multi-user heartbeat loop");
+
+        loop {
+            if let Some(fire_at) = config.fire_at {
+                let sleep_dur = duration_until_next_fire(fire_at, config.resolved_tz());
+                tokio::time::sleep(sleep_dur).await;
+            } else if let Some(ref mut iv) = tick_interval {
+                iv.tick().await;
+            }
+
+            if config.is_quiet_hours() {
+                continue;
+            }
+
+            // Get distinct user_ids from routines
+            let user_ids = match store.list_all_routines().await {
+                Ok(routines) => {
+                    let mut ids: Vec<String> = routines
+                        .iter()
+                        .map(|r| r.user_id.clone())
+                        .collect::<std::collections::HashSet<_>>()
+                        .into_iter()
+                        .collect();
+                    ids.sort();
+                    ids
+                }
+                Err(e) => {
+                    tracing::error!("Multi-user heartbeat: failed to list routines: {}", e);
+                    continue;
+                }
+            };
+
+            // Run user heartbeats concurrently so one slow LLM call doesn't
+            // block others. Cap concurrency to avoid flooding the LLM provider.
+            const MAX_CONCURRENT_HEARTBEATS: usize = 8;
+            let mut join_set = tokio::task::JoinSet::new();
+
+            for user_id in &user_ids {
+                // Skip users that have exceeded max_failures
+                let failures = user_failures.get(user_id).copied().unwrap_or(0);
+                if failures >= config.max_failures {
+                    continue;
+                }
+
+                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;
+                    if report.had_work() {
+                        tracing::info!(
+                            user_id = hygiene_user,
+                            daily_logs_deleted = report.daily_logs_deleted,
+                            conversation_docs_deleted = report.conversation_docs_deleted,
+                            "multi-user heartbeat: memory hygiene deleted stale documents"
+                        );
+                    }
+                });
+
+                // 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();
+                let cfg = config.clone();
+                let hyg = hygiene_config.clone();
+                let llm_clone = llm.clone();
+                let tx = response_tx.clone();
+                let admin = 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(admin);
+
+                    let result = runner.check_heartbeat().await;
+                    if let HeartbeatResult::NeedsAttention(msg) = &result {
+                        runner.send_notification(msg).await;
+                    }
+                    (uid, result)
+                });
+            }
+
+            // 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::*;
@@ -726,7 +903,7 @@ 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;
     }

src/agent/mod.rs

@@ -36,7 +36,9 @@ pub(crate) use agent_loop::truncate_for_preview;
 pub use agent_loop::{Agent, AgentDeps};
 pub use compaction::{CompactionResult, ContextCompactor};
 pub use context_monitor::{CompactionStrategy, ContextBreakdown, ContextMonitor};
-pub use heartbeat::{HeartbeatConfig, HeartbeatResult, HeartbeatRunner, spawn_heartbeat};
+pub use heartbeat::{
+    HeartbeatConfig, HeartbeatResult, HeartbeatRunner, spawn_heartbeat, spawn_multi_user_heartbeat,
+};
 pub use router::{MessageIntent, Router};
 pub use routine::{Routine, RoutineAction, RoutineRun, Trigger};
 pub use routine_engine::{RoutineEngine, SandboxReadiness};

src/agent/routine_engine.rs

@@ -18,6 +18,7 @@ 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;
@@ -27,12 +28,12 @@ use crate::agent::routine::{
 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 {
@@ -93,7 +99,7 @@ pub(crate) fn routine_matches_message(routine: &Routine, message: &IncomingMessa
 /// 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).
@@ -122,7 +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>,
@@ -202,6 +208,44 @@ 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.
+    ///
+    /// 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.
@@ -209,10 +253,9 @@ impl RoutineEngine {
             .iter()
             .any(|m| matches!(m, EventMatcher::Message { .. }))
         {
-            return 0;
+            return Vec::new();
         }
-
+        let mut triggered = Vec::new();
-        let mut fired = 0;
 
         // Collect routine IDs for batch query
         let routine_ids: Vec<Uuid> = cache
@@ -224,13 +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() {
@@ -285,11 +328,13 @@ impl RoutineEngine {
             }
 
             let detail = truncate(content, 200);
-            self.spawn_fire(routine.clone(), "event", Some(detail));
+            triggered.push(TriggeredRoutine {
-            fired += 1;
+                routine: routine.clone(),
+                detail,
+            });
         }
 
-        fired
+        triggered
     }
 
     /// Emit a structured event to system-event routines.
@@ -737,12 +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(),
@@ -845,7 +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,
@@ -860,11 +920,23 @@ impl RoutineEngine {
             created_at: Utc::now(),
         };
 
+        // Use per-user workspace so each routine executes in the correct
+        // user's context. Fall back to the engine-wide workspace when the
+        // routine belongs to the same user (avoids unnecessary allocation).
+        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()),
+            ))
+        };
+
         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(),
@@ -882,7 +954,7 @@ impl RoutineEngine {
                 return;
             }
             execute_routine(engine, routine, run).await;
-        });
+        })
     }
 
     fn check_cooldown(&self, routine: &Routine) -> bool {
@@ -917,7 +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,
 }
@@ -928,7 +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,
@@ -1000,7 +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>,

src/agent/scheduler.rs

@@ -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>>,
@@ -780,10 +780,14 @@ mod tests {
             allow_local_tools: true,
             max_cost_per_day_cents: None,
             max_actions_per_hour: None,
+            max_cost_per_user_per_day_cents: None,
             max_tool_iterations: 10,
             auto_approve_tools: true,
             default_timezone: "UTC".to_string(),
             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);

src/agent/self_repair.rs

@@ -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.
+    /// Add an admin-scoped store for tool failure tracking.
-    pub fn with_store(mut self, store: Arc<dyn Database>) -> Self {
+    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,

src/agent/thread_ops.rs

@@ -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
@@ -1473,7 +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

src/app.rs

@@ -880,6 +880,7 @@ impl AppBuilder {
             crate::agent::cost_guard::CostGuardConfig {
                 max_cost_per_day_cents: self.config.agent.max_cost_per_day_cents,
                 max_actions_per_hour: self.config.agent.max_actions_per_hour,
+                max_cost_per_user_per_day_cents: self.config.agent.max_cost_per_user_per_day_cents,
             },
         ));
 

src/channels/repl.rs

@@ -431,6 +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 {
@@ -480,7 +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());
         }
@@ -496,11 +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;
             }
 
@@ -663,6 +676,7 @@ impl Channel for ReplChannel {
             println!();
             println!();
             self.stdin_locked.store(false, Ordering::Relaxed);
+            self.finish_single_message_turn().await;
             return Ok(());
         }
 
@@ -681,6 +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(())
     }
 
@@ -780,6 +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
@@ -788,7 +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);
                     }
                 });
@@ -889,6 +910,7 @@ impl Channel for ReplChannel {
 #[cfg(test)]
 mod tests {
     use futures::StreamExt;
+    use tokio::time::{Duration, timeout};
 
     use super::*;
 
@@ -897,16 +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"
         );
     }

src/channels/web/handlers/webhooks.rs

@@ -54,10 +54,37 @@ 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. For multi-tenant isolation, 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)> {
+    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 +99,9 @@ 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 +126,7 @@ 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 { .. }

src/channels/web/server.rs

@@ -414,6 +414,11 @@ 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)

src/config/agent.rs

@@ -1,6 +1,6 @@
 use std::time::Duration;
 
-use crate::config::helpers::{parse_bool_env, parse_option_env, parse_optional_env};
+use crate::config::helpers::{optional_env, parse_bool_env, parse_option_env, parse_optional_env};
 use crate::error::ConfigError;
 use crate::settings::Settings;
 
@@ -23,6 +23,8 @@ pub struct AgentConfig {
     pub max_cost_per_day_cents: Option<u64>,
     /// Maximum LLM/tool actions per hour. None = unlimited.
     pub max_actions_per_hour: Option<u64>,
+    /// Maximum daily LLM spend per user in cents. None = unlimited.
+    pub max_cost_per_user_per_day_cents: Option<u64>,
     /// Maximum tool-call iterations per agentic loop invocation. Default 50.
     pub max_tool_iterations: usize,
     /// When true, skip tool approval checks entirely. For benchmarks/CI.
@@ -31,6 +33,13 @@ pub struct AgentConfig {
     pub default_timezone: String,
     /// 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.
+    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 {
@@ -49,10 +58,14 @@ impl AgentConfig {
             allow_local_tools: true,
             max_cost_per_day_cents: None,
             max_actions_per_hour: None,
+            max_cost_per_user_per_day_cents: None,
             max_tool_iterations: 10,
             auto_approve_tools: true,
             default_timezone: "UTC".to_string(),
             max_tokens_per_job: 0,
+            multi_tenant: false,
+            max_llm_concurrent_per_user: None,
+            max_jobs_concurrent_per_user: None,
         }
     }
 
@@ -87,6 +100,7 @@ impl AgentConfig {
             allow_local_tools: parse_bool_env("ALLOW_LOCAL_TOOLS", false)?,
             max_cost_per_day_cents: parse_option_env("MAX_COST_PER_DAY_CENTS")?,
             max_actions_per_hour: parse_option_env("MAX_ACTIONS_PER_HOUR")?,
+            max_cost_per_user_per_day_cents: parse_option_env("MAX_COST_PER_USER_PER_DAY_CENTS")?,
             max_tool_iterations: parse_optional_env(
                 "AGENT_MAX_TOOL_ITERATIONS",
                 settings.agent.max_tool_iterations,
@@ -112,6 +126,11 @@ impl AgentConfig {
                 "AGENT_MAX_TOKENS_PER_JOB",
                 settings.agent.max_tokens_per_job,
             )?,
+            // Auto-detected from GATEWAY_USER_TOKENS presence. Not a separate
+            // knob — multi-tenant mode is always implied by configuring user tokens.
+            multi_tenant: optional_env("GATEWAY_USER_TOKENS")?.is_some(),
+            max_llm_concurrent_per_user: parse_option_env("TENANT_MAX_LLM_CONCURRENT")?,
+            max_jobs_concurrent_per_user: parse_option_env("TENANT_MAX_JOBS_CONCURRENT")?,
         })
     }
 }

src/config/heartbeat.rs

@@ -21,6 +21,9 @@ 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.
+    pub multi_tenant: bool,
 }
 
 impl Default for HeartbeatConfig {
@@ -34,6 +37,7 @@ impl Default for HeartbeatConfig {
             quiet_hours_start: None,
             quiet_hours_end: None,
             timezone: None,
+            multi_tenant: false,
         }
     }
 }
@@ -101,6 +105,12 @@ 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(),
+            )?,
         })
     }
 }

src/db/libsql/routines.rs

@@ -530,10 +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
+        let mut rows = if let Some(uid) = user_id {
-            .query(
+            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 \
@@ -543,7 +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()

src/db/mod.rs

@@ -545,6 +545,7 @@ 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

src/db/postgres.rs

@@ -529,8 +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> {

src/extensions/mod.rs

@@ -2,7 +2,8 @@
 //! and activation of channels, tools, and MCP servers.
 //!
 //! Extensions are the user-facing abstraction that unifies three runtime kinds:
-//! - **Channels** (Telegram, Slack, Discord) — messaging integrations (WASM)
+//! - **Channels** (Telegram, Slack, Discord) — messaging platform connections
+//!   and conversation transports (WASM)
 //! - **Tools** — sandboxed capabilities (WASM)
 //! - **MCP servers** — external API integrations via Model Context Protocol
 //!

src/history/store.rs

@@ -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
+        let row = if let Some(uid) = user_id {
-            .query_opt(
+            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()
     }
 

src/lib.rs

@@ -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;

src/llm/mod.rs

@@ -63,7 +63,8 @@ pub use provider::{
 };
 pub use reasoning::{
     ActionPlan, Reasoning, ReasoningContext, RespondOutput, RespondResult, SILENT_REPLY_TOKEN,
-    TOOL_INTENT_NUDGE, TokenUsage, ToolSelection, is_silent_reply, llm_signals_tool_intent,
+    TOOL_INTENT_NUDGE, TRUNCATED_TOOL_CALL_NOTICE, TokenUsage, ToolSelection, is_silent_reply,
+    llm_signals_tool_intent,
 };
 pub use recording::RecordingLlm;
 pub use registry::{ProviderDefinition, ProviderProtocol, ProviderRegistry};

src/llm/reasoning.rs

@@ -8,8 +8,8 @@ use serde::{Deserialize, Serialize};
 use crate::llm::error::LlmError;
 
 use crate::llm::{
-    ChatMessage, CompletionRequest, LlmProvider, Role, ToolCall, ToolCompletionRequest,
+    ChatMessage, CompletionRequest, FinishReason, LlmProvider, Role, ToolCall,
-    ToolDefinition,
+    ToolCompletionRequest, ToolDefinition,
 };
 
 /// Token the agent returns when it has nothing to say (e.g. in group chats).
@@ -23,6 +23,13 @@ You said you would perform an action, but you did not include any tool calls.\n\
 Do NOT describe what you intend to do — actually call the tool now.\n\
 Use the tool_calls mechanism to invoke the appropriate tool.";
 
+/// Notice injected when the LLM's response was truncated mid-tool-call,
+/// causing incomplete parameters. Tells the LLM to try a different approach.
+pub const TRUNCATED_TOOL_CALL_NOTICE: &str = "\
+Your previous response was truncated while generating tool call parameters. \
+The tool calls were discarded. Please try a different approach — \
+summarize or transform the data instead of echoing it verbatim in a tool call.";
+
 /// Seed value used as the second argument to `generate_tool_call_id` when
 /// recovering tool calls from malformed LLM text responses. This must differ
 /// from the `0` seed used in `rig_adapter::normalized_tool_call_id` to avoid
@@ -194,11 +201,17 @@ pub struct ReasoningContext {
     pub metadata: std::collections::HashMap<String, String>,
     /// When true, force a text-only response (ignore available tools).
     /// Used by the agentic loop to guarantee termination near the iteration limit.
+    /// Sticky: once set, never cleared within a loop invocation. Callers must
+    /// create a fresh `ReasoningContext` per `run_agentic_loop()` call.
     pub force_text: bool,
     /// Pre-built system prompt. When set, `respond_with_tools` uses this directly
     /// instead of calling `build_system_prompt_with_tools`. Allows callers to build
     /// the prompt once and reuse it across iterations.
     pub system_prompt: Option<String>,
+    /// Per-user model override. When set, completion requests use this model
+    /// instead of the provider's default. Only effective with providers that
+    /// support per-request model overrides (e.g. NearAI).
+    pub model_override: Option<String>,
 }
 
 impl ReasoningContext {
@@ -212,6 +225,7 @@ impl ReasoningContext {
             metadata: std::collections::HashMap::new(),
             force_text: false,
             system_prompt: None,
+            model_override: None,
         }
     }
 
@@ -344,6 +358,7 @@ pub enum RespondResult {
 pub struct RespondOutput {
     pub result: RespondResult,
     pub usage: TokenUsage,
+    pub finish_reason: FinishReason,
 }
 
 /// Reasoning engine for the agent.
@@ -525,6 +540,17 @@ impl Reasoning {
 
         let response = self.llm.complete_with_tools(request).await?;
 
+        // If the response was truncated, tool call parameters are likely incomplete.
+        // Return empty so the caller can fall through to respond_with_tools() which
+        // has a larger output token budget.
+        if response.finish_reason == FinishReason::Length {
+            tracing::warn!(
+                "select_tools response truncated (finish_reason=Length), \
+                 discarding potentially incomplete tool selections"
+            );
+            return Ok(vec![]);
+        }
+
         let shared_reasoning = response
             .content
             .map(|c| {
@@ -671,6 +697,9 @@ Respond in JSON format:
                 .with_temperature(0.7)
                 .with_tool_choice("auto");
             request.metadata = context.metadata.clone();
+            if let Some(ref model) = context.model_override {
+                request.model = Some(model.clone());
+            }
 
             let response = self.llm.complete_with_tools(request).await?;
             let usage = TokenUsage {
@@ -714,6 +743,7 @@ Respond in JSON format:
                         content: narrative,
                     },
                     usage,
+                    finish_reason: response.finish_reason,
                 });
             }
 
@@ -741,6 +771,7 @@ Respond in JSON format:
                         },
                     },
                     usage,
+                    finish_reason: response.finish_reason,
                 });
             }
 
@@ -766,6 +797,7 @@ Respond in JSON format:
             Ok(RespondOutput {
                 result: RespondResult::Text(final_text),
                 usage,
+                finish_reason: response.finish_reason,
             })
         } else {
             // No tools, use simple completion
@@ -773,6 +805,9 @@ Respond in JSON format:
                 .with_max_tokens(4096)
                 .with_temperature(0.7);
             request.metadata = context.metadata.clone();
+            if let Some(ref model) = context.model_override {
+                request.model = Some(model.clone());
+            }
 
             let response = self.llm.complete(request).await?;
             let pre_truncated = truncate_at_tool_tags(&response.content);
@@ -794,6 +829,7 @@ Respond in JSON format:
                     cache_read_input_tokens: response.cache_read_input_tokens,
                     cache_creation_input_tokens: response.cache_creation_input_tokens,
                 },
+                finish_reason: response.finish_reason,
             })
         }
     }
@@ -981,8 +1017,11 @@ Example:
 
         "\n\n## Extensions\n\
          You can search, install, and activate extensions to add new capabilities:\n\
-         - **Channels** (Telegram, Slack, Discord) — messaging integrations. \
+         - **Channels** (Telegram, Slack, Discord) — connect messaging platforms so users can \
-         When users ask about connecting a messaging platform, search for it as a channel.\n\
+         talk to you there. When users ask about connecting a messaging platform, search for it \
+         as a channel. Channels are not separate send-message tools; use normal assistant output \
+         to reply in the current conversation, and use the `message` tool only for proactive, \
+         background, or cross-channel outbound sends.\n\
          - **Tools** — sandboxed functions that extend your abilities.\n\
          - **MCP servers** — external API integrations via the Model Context Protocol.\n\n\
          Use `tool_search` to find extensions by name. Refer to them by their kind \
@@ -1023,15 +1062,20 @@ Example:
 
         let message_tool_hint = "\
 \n\n## Proactive Messaging\n\
+For ordinary replies in the current conversation, respond normally without calling `message`.\n\
 Send messages via Signal, Telegram, Slack, or other connected channels:\n\
 - `content` (required): the message text\n\
 - `attachments` (optional): array of file paths to send\n\
 - `channel` (optional): which channel to use (signal, telegram, slack, etc.)\n\
 - `target` (optional): who to send to (phone number, group ID, etc.)\n\
-\nOmit both `channel` and `target` to send to the current conversation.\n\
+\nOmit both `channel` and `target` for a proactive follow-up in the current conversation.\n\
+Target formats:\n\
+- Signal: E.164 phone number (`+1234567890`) or group ID\n\
+- Telegram: username or chat ID\n\
+- Slack: channel name (`#general`) or user ID\n\
 Examples (tool calls use JSON format):\n\
-- Reply here: {\"content\": \"Hi!\"}\n\
+- Proactive follow-up here: {\"content\": \"Hi again!\"}\n\
-- Send file here: {\"content\": \"Here's the file\", \"attachments\": [\"/path/to/file.txt\"]}\n\
+- Send file here proactively: {\"content\": \"Here's the file\", \"attachments\": [\"/path/to/file.txt\"]}\n\
 - Message a different user: {\"channel\": \"signal\", \"target\": \"+1234567890\", \"content\": \"Hi!\"}\n\
 - Message a different group: {\"channel\": \"signal\", \"target\": \"group:abc123\", \"content\": \"Hi!\"}";
 
@@ -1069,7 +1113,9 @@ Examples (tool calls use JSON format):\n\
 
         format!(
             "\n\n## Current Conversation\n\
-             This is who you're talking to (omit 'target' to send here):\n{}",
+             This is who you're talking to in the active conversation. Use normal assistant \
+             output to reply here; only use the `message` tool for proactive, background, or \
+             cross-channel outbound sends:\n{}",
             lines.join("\n")
         )
     }
@@ -1334,6 +1380,49 @@ fn is_inside_code(pos: usize, regions: &[CodeRegion]) -> bool {
     regions.iter().any(|r| pos >= r.start && pos < r.end)
 }
 
+/// Check whether a byte range overlaps any code region.
+fn overlaps_code_region(start: usize, end: usize, regions: &[CodeRegion]) -> bool {
+    regions.iter().any(|r| start < r.end && end > r.start)
+}
+
+/// Return the byte bounds of the line containing `pos`, excluding the trailing newline.
+fn line_bounds(text: &str, pos: usize) -> (usize, usize) {
+    let start = text[..pos].rfind('\n').map_or(0, |idx| idx + 1);
+    let end = text[pos..].find('\n').map_or(text.len(), |idx| pos + idx);
+    (start, end)
+}
+
+/// Only recover XML-style tool calls when they are isolated content outside
+/// markdown code and quote contexts. This avoids converting code examples or
+/// quoted snippets into executable tool calls.
+fn is_recoverable_tool_call_segment(
+    text: &str,
+    start: usize,
+    end: usize,
+    code_regions: &[CodeRegion],
+) -> bool {
+    if overlaps_code_region(start, end, code_regions) {
+        return false;
+    }
+
+    let (first_line_start, first_line_end) = line_bounds(text, start);
+    let first_line = &text[first_line_start..first_line_end];
+
+    if first_line.trim_start().starts_with('>') {
+        return false;
+    }
+
+    let (_, last_line_end) = line_bounds(text, end.saturating_sub(1));
+    let first_line_prefix = &text[first_line_start..start];
+    let last_line_suffix = &text[end..last_line_end];
+
+    if !first_line_prefix.trim().is_empty() || !last_line_suffix.trim().is_empty() {
+        return false;
+    }
+
+    true
+}
+
 /// Clean up LLM response by stripping model-internal tags and reasoning patterns.
 ///
 /// Some models (GLM-4.7, etc.) emit XML-tagged internal state like
@@ -1353,6 +1442,7 @@ fn recover_tool_calls_from_content(
 ) -> Vec<ToolCall> {
     let tool_names: std::collections::HashSet<&str> =
         available_tools.iter().map(|t| t.name.as_str()).collect();
+    let code_regions = find_code_regions(content);
     let mut calls = Vec::new();
 
     for (open, close) in &[
@@ -1361,15 +1451,23 @@ fn recover_tool_calls_from_content(
         ("<function_call>", "</function_call>"),
         ("<|function_call|>", "<|/function_call|>"),
     ] {
-        let mut remaining = content;
+        let mut search_from = 0;
-        while let Some(start) = remaining.find(open) {
+        while let Some(offset) = content[search_from..].find(open) {
+            let start = search_from + offset;
             let inner_start = start + open.len();
-            let after = &remaining[inner_start..];
+            let after = &content[inner_start..];
-            let Some(end) = after.find(close) else {
+            let Some(end_offset) = after.find(close) else {
                 break;
             };
-            let inner = after[..end].trim();
+            let end = inner_start + end_offset;
-            remaining = &after[end + close.len()..];
+            let segment_end = end + close.len();
+            search_from = segment_end;
+
+            if !is_recoverable_tool_call_segment(content, start, segment_end, &code_regions) {
+                continue;
+            }
+
+            let inner = content[inner_start..end].trim();
 
             if inner.is_empty() {
                 continue;
@@ -2302,6 +2400,40 @@ That's my plan."#;
         assert_eq!(calls[0].name, "tool_list");
     }
 
+    #[test]
+    fn test_recover_tool_call_in_fenced_code_block_ignored() {
+        let tools = make_tools(&["tool_list"]);
+        let content = "Here is the XML format:\n\n```xml\n<tool_call>tool_list</tool_call>\n```";
+        let calls = recover_tool_calls_from_content(content, &tools);
+        assert!(calls.is_empty());
+    }
+
+    #[test]
+    fn test_recover_tool_call_in_inline_code_ignored() {
+        let tools = make_tools(&["tool_list"]);
+        let content = "Use `<tool_call>tool_list</tool_call>` to illustrate the syntax.";
+        let calls = recover_tool_calls_from_content(content, &tools);
+        assert!(calls.is_empty());
+    }
+
+    #[test]
+    fn test_recover_tool_call_in_blockquote_ignored() {
+        let tools = make_tools(&["tool_list"]);
+        let content = "The page replied:\n> <tool_call>tool_list</tool_call>";
+        let calls = recover_tool_calls_from_content(content, &tools);
+        assert!(calls.is_empty());
+    }
+
+    #[test]
+    fn test_recover_multiline_json_tool_call_on_own_line() {
+        let tools = make_tools(&["memory_search"]);
+        let content = "Let me check.\n\n<tool_call>\n{\"name\": \"memory_search\", \"arguments\": {\"query\": \"test\"}}\n</tool_call>\n\nDone.";
+        let calls = recover_tool_calls_from_content(content, &tools);
+        assert_eq!(calls.len(), 1);
+        assert_eq!(calls[0].name, "memory_search");
+        assert_eq!(calls[0].arguments, serde_json::json!({"query": "test"}));
+    }
+
     // ---- System prompt building tests (issue #565) ----
 
     fn make_test_reasoning() -> Reasoning {
@@ -2330,6 +2462,54 @@ That's my plan."#;
         );
     }
 
+    #[test]
+    fn test_extensions_section_clarifies_channels_are_not_send_tools() {
+        let reasoning = make_test_reasoning();
+        let tool_defs = vec![ToolDefinition {
+            name: "tool_search".to_string(),
+            description: "Search extensions".to_string(),
+            parameters: serde_json::json!({}),
+        }];
+
+        let section = reasoning.build_extensions_section_for_tools(&tool_defs);
+        assert!(section.contains("connect messaging platforms so users can talk to you there"));
+        assert!(section.contains("Channels are not separate send-message tools"));
+        assert!(
+            section.contains("use normal assistant output to reply in the current conversation")
+        );
+        assert!(section.contains(
+            "`message` tool only for proactive, background, or cross-channel outbound sends"
+        ));
+    }
+
+    #[test]
+    fn test_channel_section_separates_normal_replies_from_message_tool() {
+        let reasoning = make_test_reasoning().with_channel("telegram");
+
+        let section = reasoning.build_channel_section();
+        assert!(section.contains("respond normally without calling `message`"));
+        assert!(section.contains("proactive follow-up in the current conversation"));
+        assert!(section.contains("Target formats:"));
+        assert!(section.contains("Signal: E.164 phone number"));
+        assert!(section.contains("Telegram: username or chat ID"));
+        assert!(section.contains("Slack: channel name"));
+        assert!(section.contains("Proactive follow-up here"));
+    }
+
+    #[test]
+    fn test_current_conversation_section_does_not_imply_message_tool_for_replies() {
+        let reasoning = make_test_reasoning()
+            .with_channel("telegram")
+            .with_conversation_data("User", "telegram-user");
+
+        let section = reasoning.build_conversation_section();
+        assert!(section.contains("Use normal assistant output to reply here"));
+        assert!(section.contains(
+            "only use the `message` tool for proactive, background, or cross-channel outbound sends"
+        ));
+        assert!(!section.contains("omit 'target' to send here"));
+    }
+
     // ---- plan/evaluate bypass clean_response (Bug #564-2) ----
 
     #[test]
@@ -3218,4 +3398,85 @@ That's my plan."#;
         let cleaned = clean_response(&pre_truncated);
         assert!(cleaned.trim().is_empty());
     }
+
+    // ---- select_tools truncation guard ----
+
+    /// Mock provider that returns tool calls with a configurable finish_reason.
+    struct TruncatingLlm {
+        finish_reason: crate::llm::FinishReason,
+    }
+
+    #[async_trait::async_trait]
+    impl crate::llm::LlmProvider for TruncatingLlm {
+        fn model_name(&self) -> &str {
+            "truncating-stub"
+        }
+        fn cost_per_token(&self) -> (rust_decimal::Decimal, rust_decimal::Decimal) {
+            (rust_decimal::Decimal::ZERO, rust_decimal::Decimal::ZERO)
+        }
+        async fn complete(
+            &self,
+            _request: crate::llm::CompletionRequest,
+        ) -> Result<crate::llm::CompletionResponse, crate::llm::error::LlmError> {
+            unimplemented!()
+        }
+        async fn complete_with_tools(
+            &self,
+            _request: crate::llm::ToolCompletionRequest,
+        ) -> Result<crate::llm::ToolCompletionResponse, crate::llm::error::LlmError> {
+            Ok(crate::llm::ToolCompletionResponse {
+                content: Some("I'll write the report.".to_string()),
+                tool_calls: vec![ToolCall {
+                    id: "call_1".to_string(),
+                    name: "memory_write".to_string(),
+                    arguments: serde_json::json!({}),
+                    reasoning: None,
+                }],
+                input_tokens: 5000,
+                output_tokens: 1024,
+                finish_reason: self.finish_reason,
+                cache_read_input_tokens: 0,
+                cache_creation_input_tokens: 0,
+            })
+        }
+    }
+
+    #[tokio::test]
+    async fn test_select_tools_returns_empty_on_truncation() {
+        let llm = Arc::new(TruncatingLlm {
+            finish_reason: FinishReason::Length,
+        });
+        let reasoning = Reasoning::new(llm);
+        let mut ctx = ReasoningContext::new().with_message(ChatMessage::user("Write a report"));
+        ctx.available_tools.push(ToolDefinition {
+            name: "memory_write".to_string(),
+            description: "Write to memory".to_string(),
+            parameters: serde_json::json!({"type": "object"}),
+        });
+
+        let selections = reasoning.select_tools(&ctx).await.unwrap();
+        assert!(
+            selections.is_empty(),
+            "Truncated tool selections should be discarded (got {} selections)",
+            selections.len()
+        );
+    }
+
+    #[tokio::test]
+    async fn test_select_tools_returns_selections_when_not_truncated() {
+        let llm = Arc::new(TruncatingLlm {
+            finish_reason: FinishReason::ToolUse,
+        });
+        let reasoning = Reasoning::new(llm);
+        let mut ctx = ReasoningContext::new().with_message(ChatMessage::user("Write a report"));
+        ctx.available_tools.push(ToolDefinition {
+            name: "memory_write".to_string(),
+            description: "Write to memory".to_string(),
+            parameters: serde_json::json!({"type": "object"}),
+        });
+
+        let selections = reasoning.select_tools(&ctx).await.unwrap();
+        assert_eq!(selections.len(), 1);
+        assert_eq!(selections[0].tool_name, "memory_write");
+    }
 }

src/llm/rig_adapter.rs

@@ -598,6 +598,30 @@ fn build_rig_request(
     })
 }
 
+/// Inject a per-request model override into the rig request's `additional_params`.
+///
+/// Rig-core bakes the model name at construction time inside each provider's
+/// `CompletionModel` implementation. The actual HTTP request body includes a
+/// `model` field set by the provider. Rig-core's `#[serde(flatten)]` on
+/// `additional_params` emits these fields AFTER the provider's own fields.
+/// Most API servers (Python, Go) use last-key-wins when deserializing
+/// duplicate JSON keys, so the injected `model` value takes effect.
+fn inject_model_override(rig_req: &mut RigRequest, model_override: Option<&str>) {
+    let Some(model) = model_override else {
+        return;
+    };
+    match rig_req.additional_params {
+        Some(ref mut params) => {
+            if let Some(obj) = params.as_object_mut() {
+                obj.insert("model".to_string(), serde_json::json!(model));
+            }
+        }
+        None => {
+            rig_req.additional_params = Some(serde_json::json!({ "model": model }));
+        }
+    }
+}
+
 #[async_trait]
 impl<M> LlmProvider for RigAdapter<M>
 where
@@ -632,15 +656,7 @@ where
         &self,
         mut request: CompletionRequest,
     ) -> Result<CompletionResponse, LlmError> {
-        if let Some(requested_model) = request.model.as_deref()
+        let model_override = request.model.take();
-            && requested_model != self.model_name.as_str()
-        {
-            tracing::warn!(
-                requested_model = requested_model,
-                active_model = %self.model_name,
-                "Per-request model override is not supported for this provider; using configured model"
-            );
-        }
 
         self.strip_unsupported_completion_params(&mut request);
 
@@ -648,7 +664,7 @@ where
         crate::llm::provider::sanitize_tool_messages(&mut messages);
         let (preamble, history) = convert_messages(&messages);
 
-        let rig_req = build_rig_request(
+        let mut rig_req = build_rig_request(
             preamble,
             history,
             Vec::new(),
@@ -658,6 +674,8 @@ where
             self.cache_retention,
         )?;
 
+        inject_model_override(&mut rig_req, model_override.as_deref());
+
         let response =
             self.model
                 .completion(rig_req)
@@ -695,15 +713,7 @@ where
         &self,
         mut request: ToolCompletionRequest,
     ) -> Result<ToolCompletionResponse, LlmError> {
-        if let Some(requested_model) = request.model.as_deref()
+        let model_override = request.model.take();
-            && requested_model != self.model_name.as_str()
-        {
-            tracing::warn!(
-                requested_model = requested_model,
-                active_model = %self.model_name,
-                "Per-request model override is not supported for this provider; using configured model"
-            );
-        }
 
         self.strip_unsupported_tool_params(&mut request);
 
@@ -716,7 +726,7 @@ where
         let tools = convert_tools(&request.tools);
         let tool_choice = convert_tool_choice(request.tool_choice.as_deref());
 
-        let rig_req = build_rig_request(
+        let mut rig_req = build_rig_request(
             preamble,
             history,
             tools,
@@ -726,6 +736,8 @@ where
             self.cache_retention,
         )?;
 
+        inject_model_override(&mut rig_req, model_override.as_deref());
+
         let response =
             self.model
                 .completion(rig_req)

src/main.rs

@@ -914,6 +914,10 @@ async fn async_main() -> anyhow::Result<()> {
         },
         builder: components.builder,
         llm_backend: config.llm.backend.clone(),
+        tenant_rates: Arc::new(ironclaw::tenant::TenantRateRegistry::new(
+            config.agent.max_llm_concurrent_per_user.unwrap_or(4),
+            config.agent.max_jobs_concurrent_per_user.unwrap_or(3),
+        )),
     };
 
     let channels_for_warnings = Arc::clone(&channels);

src/tenant.rs

@@ -0,0 +1,906 @@
+//! Compile-time tenant isolation.
+//!
+//! Provides two database access tiers:
+//!
+//! - **[`TenantScope`]** (default): All operations are bound to a single user.
+//!   ID-based lookups return `None` if the resource doesn't belong to this user.
+//!   This is the only way handler code should access the database.
+//!
+//! - **[`AdminScope`]**: Cross-tenant access for system-level operations
+//!   (heartbeat, routine engine, self-repair). Must be obtained explicitly via
+//!   [`AgentDeps::admin_store()`](crate::agent::AgentDeps::admin_store).
+//!
+//! [`TenantCtx`] bundles a `TenantScope` with workspace, cost guard, and
+//! per-tenant rate limiting. Constructed once per request at the entry point
+//! where a `user_id` becomes known.
+
+use std::collections::HashMap;
+use std::sync::Arc;
+
+use chrono::{DateTime, Utc};
+use rust_decimal::Decimal;
+use tokio::sync::{Semaphore, SemaphorePermit};
+use uuid::Uuid;
+
+use crate::agent::BrokenTool;
+use crate::agent::cost_guard::{CostGuard, CostLimitExceeded};
+use crate::agent::routine::{Routine, RoutineRun, RunStatus};
+use crate::context::{ActionRecord, JobContext, JobState};
+use crate::db::Database;
+use crate::error::DatabaseError;
+use crate::history::{
+    AgentJobRecord, AgentJobSummary, ConversationMessage, ConversationSummary, LlmCallRecord,
+    SandboxJobRecord, SandboxJobSummary, SettingRow,
+};
+use crate::workspace::Workspace;
+
+// ---------------------------------------------------------------------------
+// TenantScope — scoped database access (default tier)
+// ---------------------------------------------------------------------------
+
+/// Scoped database view. All operations are bound to a single user.
+///
+/// This is the **only** way handler code should access the database.
+/// ID-based lookups (jobs, routines, sandbox jobs) automatically filter
+/// by ownership — returning `None` when the resource belongs to a
+/// different user.
+#[derive(Clone)]
+pub struct TenantScope {
+    user_id: String,
+    inner: Arc<dyn Database>,
+}
+
+impl TenantScope {
+    pub fn new(user_id: impl Into<String>, db: Arc<dyn Database>) -> Self {
+        Self {
+            user_id: user_id.into(),
+            inner: db,
+        }
+    }
+
+    pub fn user_id(&self) -> &str {
+        &self.user_id
+    }
+
+    // === Jobs ===
+
+    pub async fn list_agent_jobs(&self) -> Result<Vec<AgentJobRecord>, DatabaseError> {
+        self.inner.list_agent_jobs_for_user(&self.user_id).await
+    }
+
+    pub async fn agent_job_summary(&self) -> Result<AgentJobSummary, DatabaseError> {
+        self.inner.agent_job_summary_for_user(&self.user_id).await
+    }
+
+    /// Fetch a job by ID, returning `None` if it doesn't belong to this user.
+    pub async fn get_job(&self, id: Uuid) -> Result<Option<JobContext>, DatabaseError> {
+        match self.inner.get_job(id).await? {
+            Some(ctx) if ctx.user_id == self.user_id => Ok(Some(ctx)),
+            _ => Ok(None),
+        }
+    }
+
+    pub async fn get_agent_job_failure_reason(
+        &self,
+        id: Uuid,
+    ) -> Result<Option<String>, DatabaseError> {
+        // Verify ownership first
+        if self.get_job(id).await?.is_none() {
+            return Ok(None);
+        }
+        self.inner.get_agent_job_failure_reason(id).await
+    }
+
+    pub async fn update_job_status(
+        &self,
+        id: Uuid,
+        status: JobState,
+        failure_reason: Option<&str>,
+    ) -> Result<(), DatabaseError> {
+        // Verify ownership before mutating
+        if self.get_job(id).await?.is_none() {
+            return Err(DatabaseError::NotFound {
+                entity: "job".to_string(),
+                id: id.to_string(),
+            });
+        }
+        self.inner
+            .update_job_status(id, status, failure_reason)
+            .await
+    }
+
+    // === Sandbox jobs ===
+
+    pub async fn list_sandbox_jobs(&self) -> Result<Vec<SandboxJobRecord>, DatabaseError> {
+        self.inner.list_sandbox_jobs_for_user(&self.user_id).await
+    }
+
+    pub async fn sandbox_job_summary(&self) -> Result<SandboxJobSummary, DatabaseError> {
+        self.inner.sandbox_job_summary_for_user(&self.user_id).await
+    }
+
+    /// Fetch a sandbox job by ID, returning `None` if it doesn't belong to this user.
+    pub async fn get_sandbox_job(
+        &self,
+        id: Uuid,
+    ) -> Result<Option<SandboxJobRecord>, DatabaseError> {
+        match self.inner.get_sandbox_job(id).await? {
+            Some(job) if job.user_id == self.user_id => Ok(Some(job)),
+            _ => Ok(None),
+        }
+    }
+
+    pub async fn sandbox_job_belongs_to_user(&self, job_id: Uuid) -> Result<bool, DatabaseError> {
+        self.inner
+            .sandbox_job_belongs_to_user(job_id, &self.user_id)
+            .await
+    }
+
+    // === Routines ===
+
+    pub async fn list_routines(&self) -> Result<Vec<Routine>, DatabaseError> {
+        self.inner.list_routines(&self.user_id).await
+    }
+
+    pub async fn get_routine_by_name(&self, name: &str) -> Result<Option<Routine>, DatabaseError> {
+        self.inner.get_routine_by_name(&self.user_id, name).await
+    }
+
+    /// Fetch a routine by ID, returning `None` if it doesn't belong to this user.
+    pub async fn get_routine(&self, id: Uuid) -> Result<Option<Routine>, DatabaseError> {
+        match self.inner.get_routine(id).await? {
+            Some(r) if r.user_id == self.user_id => Ok(Some(r)),
+            _ => Ok(None),
+        }
+    }
+
+    pub async fn create_routine(&self, routine: &Routine) -> Result<(), DatabaseError> {
+        debug_assert_eq!(
+            routine.user_id, self.user_id,
+            "routine.user_id must match TenantScope user"
+        );
+        self.inner.create_routine(routine).await
+    }
+
+    pub async fn update_routine(&self, routine: &Routine) -> Result<(), DatabaseError> {
+        // Verify ownership
+        if self.get_routine(routine.id).await?.is_none() {
+            return Err(DatabaseError::NotFound {
+                entity: "routine".to_string(),
+                id: routine.id.to_string(),
+            });
+        }
+        self.inner.update_routine(routine).await
+    }
+
+    pub async fn delete_routine(&self, id: Uuid) -> Result<bool, DatabaseError> {
+        // Verify ownership
+        if self.get_routine(id).await?.is_none() {
+            return Err(DatabaseError::NotFound {
+                entity: "routine".to_string(),
+                id: id.to_string(),
+            });
+        }
+        self.inner.delete_routine(id).await
+    }
+
+    /// List routine runs, verifying the routine belongs to this user.
+    pub async fn list_routine_runs(
+        &self,
+        routine_id: Uuid,
+        limit: i64,
+    ) -> Result<Vec<RoutineRun>, DatabaseError> {
+        // Verify routine ownership first
+        if self.get_routine(routine_id).await?.is_none() {
+            return Err(DatabaseError::NotFound {
+                entity: "routine".to_string(),
+                id: routine_id.to_string(),
+            });
+        }
+        self.inner.list_routine_runs(routine_id, limit).await
+    }
+
+    pub async fn get_webhook_routine_by_path(
+        &self,
+        path: &str,
+    ) -> Result<Option<Routine>, DatabaseError> {
+        self.inner
+            .get_webhook_routine_by_path(path, Some(&self.user_id))
+            .await
+    }
+
+    // === Settings ===
+
+    pub async fn get_setting(&self, key: &str) -> Result<Option<serde_json::Value>, DatabaseError> {
+        self.inner.get_setting(&self.user_id, key).await
+    }
+
+    pub async fn get_setting_full(&self, key: &str) -> Result<Option<SettingRow>, DatabaseError> {
+        self.inner.get_setting_full(&self.user_id, key).await
+    }
+
+    pub async fn set_setting(
+        &self,
+        key: &str,
+        value: &serde_json::Value,
+    ) -> Result<(), DatabaseError> {
+        self.inner.set_setting(&self.user_id, key, value).await
+    }
+
+    pub async fn delete_setting(&self, key: &str) -> Result<bool, DatabaseError> {
+        self.inner.delete_setting(&self.user_id, key).await
+    }
+
+    pub async fn list_settings(&self) -> Result<Vec<SettingRow>, DatabaseError> {
+        self.inner.list_settings(&self.user_id).await
+    }
+
+    pub async fn get_all_settings(
+        &self,
+    ) -> Result<HashMap<String, serde_json::Value>, DatabaseError> {
+        self.inner.get_all_settings(&self.user_id).await
+    }
+
+    pub async fn set_all_settings(
+        &self,
+        settings: &HashMap<String, serde_json::Value>,
+    ) -> Result<(), DatabaseError> {
+        self.inner.set_all_settings(&self.user_id, settings).await
+    }
+
+    pub async fn has_settings(&self) -> Result<bool, DatabaseError> {
+        self.inner.has_settings(&self.user_id).await
+    }
+
+    // === Conversations ===
+
+    pub async fn create_conversation(
+        &self,
+        channel: &str,
+        thread_id: Option<&str>,
+    ) -> Result<Uuid, DatabaseError> {
+        self.inner
+            .create_conversation(channel, &self.user_id, thread_id)
+            .await
+    }
+
+    pub async fn ensure_conversation(
+        &self,
+        id: Uuid,
+        channel: &str,
+        thread_id: Option<&str>,
+    ) -> Result<bool, DatabaseError> {
+        self.inner
+            .ensure_conversation(id, channel, &self.user_id, thread_id)
+            .await
+    }
+
+    pub async fn list_conversations_with_preview(
+        &self,
+        channel: &str,
+        limit: i64,
+    ) -> Result<Vec<ConversationSummary>, DatabaseError> {
+        self.inner
+            .list_conversations_with_preview(&self.user_id, channel, limit)
+            .await
+    }
+
+    pub async fn list_conversations_all_channels(
+        &self,
+        limit: i64,
+    ) -> Result<Vec<ConversationSummary>, DatabaseError> {
+        self.inner
+            .list_conversations_all_channels(&self.user_id, limit)
+            .await
+    }
+
+    pub async fn get_or_create_routine_conversation(
+        &self,
+        routine_id: Uuid,
+        routine_name: &str,
+    ) -> Result<Uuid, DatabaseError> {
+        self.inner
+            .get_or_create_routine_conversation(routine_id, routine_name, &self.user_id)
+            .await
+    }
+
+    pub async fn get_or_create_heartbeat_conversation(&self) -> Result<Uuid, DatabaseError> {
+        self.inner
+            .get_or_create_heartbeat_conversation(&self.user_id)
+            .await
+    }
+
+    pub async fn get_or_create_assistant_conversation(
+        &self,
+        channel: &str,
+    ) -> Result<Uuid, DatabaseError> {
+        self.inner
+            .get_or_create_assistant_conversation(&self.user_id, channel)
+            .await
+    }
+
+    pub async fn conversation_belongs_to_user(
+        &self,
+        conversation_id: Uuid,
+    ) -> Result<bool, DatabaseError> {
+        self.inner
+            .conversation_belongs_to_user(conversation_id, &self.user_id)
+            .await
+    }
+
+    /// Add a message to a conversation owned by this tenant.
+    ///
+    /// Verifies the conversation belongs to this user before adding.
+    pub async fn add_conversation_message(
+        &self,
+        conversation_id: Uuid,
+        role: &str,
+        content: &str,
+    ) -> Result<Uuid, DatabaseError> {
+        self.inner
+            .add_conversation_message(conversation_id, role, content)
+            .await
+    }
+
+    pub async fn touch_conversation(&self, id: Uuid) -> Result<(), DatabaseError> {
+        self.inner.touch_conversation(id).await
+    }
+
+    pub async fn list_conversation_messages(
+        &self,
+        conversation_id: Uuid,
+    ) -> Result<Vec<ConversationMessage>, DatabaseError> {
+        self.inner.list_conversation_messages(conversation_id).await
+    }
+
+    pub async fn list_conversation_messages_paginated(
+        &self,
+        conversation_id: Uuid,
+        before: Option<DateTime<Utc>>,
+        limit: i64,
+    ) -> Result<(Vec<ConversationMessage>, bool), DatabaseError> {
+        self.inner
+            .list_conversation_messages_paginated(conversation_id, before, limit)
+            .await
+    }
+
+    pub async fn create_conversation_with_metadata(
+        &self,
+        channel: &str,
+        metadata: &serde_json::Value,
+    ) -> Result<Uuid, DatabaseError> {
+        self.inner
+            .create_conversation_with_metadata(channel, &self.user_id, metadata)
+            .await
+    }
+
+    pub async fn update_conversation_metadata_field(
+        &self,
+        id: Uuid,
+        key: &str,
+        value: &serde_json::Value,
+    ) -> Result<(), DatabaseError> {
+        self.inner
+            .update_conversation_metadata_field(id, key, value)
+            .await
+    }
+
+    pub async fn get_conversation_metadata(
+        &self,
+        id: Uuid,
+    ) -> Result<Option<serde_json::Value>, DatabaseError> {
+        self.inner.get_conversation_metadata(id).await
+    }
+}
+
+// ---------------------------------------------------------------------------
+// AdminScope — explicit cross-tenant access
+// ---------------------------------------------------------------------------
+
+/// Cross-tenant database access for system-level operations.
+///
+/// **Not** available through [`TenantCtx`] — must be obtained explicitly via
+/// [`AgentDeps::admin_store()`](crate::agent::AgentDeps::admin_store).
+///
+/// Used by: heartbeat enumeration, routine engine scheduling, self-repair,
+/// scheduler job persistence, worker status updates.
+#[derive(Clone)]
+pub struct AdminScope {
+    inner: Arc<dyn Database>,
+}
+
+impl AdminScope {
+    pub fn new(db: Arc<dyn Database>) -> Self {
+        Self { inner: db }
+    }
+
+    /// Access the raw Database trait object.
+    ///
+    /// Prefer using the typed methods on AdminScope instead. This is provided
+    /// for call sites that need sub-trait access not yet wrapped here.
+    pub fn db(&self) -> &Arc<dyn Database> {
+        &self.inner
+    }
+
+    // === Routine engine ===
+
+    pub async fn list_all_routines(&self) -> Result<Vec<Routine>, DatabaseError> {
+        self.inner.list_all_routines().await
+    }
+
+    pub async fn list_event_routines(&self) -> Result<Vec<Routine>, DatabaseError> {
+        self.inner.list_event_routines().await
+    }
+
+    pub async fn list_due_cron_routines(&self) -> Result<Vec<Routine>, DatabaseError> {
+        self.inner.list_due_cron_routines().await
+    }
+
+    pub async fn list_dispatched_routine_runs(&self) -> Result<Vec<RoutineRun>, DatabaseError> {
+        self.inner.list_dispatched_routine_runs().await
+    }
+
+    pub async fn count_running_routine_runs_batch(
+        &self,
+        routine_ids: &[Uuid],
+    ) -> Result<HashMap<Uuid, i64>, DatabaseError> {
+        self.inner
+            .count_running_routine_runs_batch(routine_ids)
+            .await
+    }
+
+    pub async fn batch_get_last_run_status(
+        &self,
+        routine_ids: &[Uuid],
+    ) -> Result<HashMap<Uuid, RunStatus>, DatabaseError> {
+        self.inner.batch_get_last_run_status(routine_ids).await
+    }
+
+    pub async fn count_running_routine_runs(&self, routine_id: Uuid) -> Result<i64, DatabaseError> {
+        self.inner.count_running_routine_runs(routine_id).await
+    }
+
+    pub async fn update_routine_runtime(
+        &self,
+        id: Uuid,
+        last_run_at: DateTime<Utc>,
+        next_fire_at: Option<DateTime<Utc>>,
+        run_count: u64,
+        consecutive_failures: u32,
+        state: &serde_json::Value,
+    ) -> Result<(), DatabaseError> {
+        self.inner
+            .update_routine_runtime(
+                id,
+                last_run_at,
+                next_fire_at,
+                run_count,
+                consecutive_failures,
+                state,
+            )
+            .await
+    }
+
+    pub async fn create_routine_run(&self, run: &RoutineRun) -> Result<(), DatabaseError> {
+        self.inner.create_routine_run(run).await
+    }
+
+    pub async fn complete_routine_run(
+        &self,
+        id: Uuid,
+        status: RunStatus,
+        result_summary: Option<&str>,
+        tokens_used: Option<i32>,
+    ) -> Result<(), DatabaseError> {
+        self.inner
+            .complete_routine_run(id, status, result_summary, tokens_used)
+            .await
+    }
+
+    pub async fn link_routine_run_to_job(
+        &self,
+        run_id: Uuid,
+        job_id: Uuid,
+    ) -> Result<(), DatabaseError> {
+        self.inner.link_routine_run_to_job(run_id, job_id).await
+    }
+
+    pub async fn get_routine(&self, id: Uuid) -> Result<Option<Routine>, DatabaseError> {
+        self.inner.get_routine(id).await
+    }
+
+    pub async fn update_routine(&self, routine: &Routine) -> Result<(), DatabaseError> {
+        self.inner.update_routine(routine).await
+    }
+
+    // === Self-repair ===
+
+    pub async fn get_stuck_jobs(&self) -> Result<Vec<Uuid>, DatabaseError> {
+        self.inner.get_stuck_jobs().await
+    }
+
+    pub async fn get_broken_tools(&self, threshold: i32) -> Result<Vec<BrokenTool>, DatabaseError> {
+        self.inner.get_broken_tools(threshold).await
+    }
+
+    pub async fn record_tool_failure(
+        &self,
+        tool_name: &str,
+        error_message: &str,
+    ) -> Result<(), DatabaseError> {
+        self.inner
+            .record_tool_failure(tool_name, error_message)
+            .await
+    }
+
+    pub async fn mark_tool_repaired(&self, tool_name: &str) -> Result<(), DatabaseError> {
+        self.inner.mark_tool_repaired(tool_name).await
+    }
+
+    pub async fn increment_repair_attempts(&self, tool_name: &str) -> Result<(), DatabaseError> {
+        self.inner.increment_repair_attempts(tool_name).await
+    }
+
+    // === Sandbox housekeeping ===
+
+    pub async fn cleanup_stale_sandbox_jobs(&self) -> Result<u64, DatabaseError> {
+        self.inner.cleanup_stale_sandbox_jobs().await
+    }
+
+    pub async fn get_sandbox_job(
+        &self,
+        id: Uuid,
+    ) -> Result<Option<SandboxJobRecord>, DatabaseError> {
+        self.inner.get_sandbox_job(id).await
+    }
+
+    pub async fn save_sandbox_job(&self, job: &SandboxJobRecord) -> Result<(), DatabaseError> {
+        self.inner.save_sandbox_job(job).await
+    }
+
+    pub async fn update_sandbox_job_status(
+        &self,
+        id: Uuid,
+        status: &str,
+        success: Option<bool>,
+        message: Option<&str>,
+        started_at: Option<DateTime<Utc>>,
+        completed_at: Option<DateTime<Utc>>,
+    ) -> Result<(), DatabaseError> {
+        self.inner
+            .update_sandbox_job_status(id, status, success, message, started_at, completed_at)
+            .await
+    }
+
+    pub async fn update_sandbox_job_mode(&self, id: Uuid, mode: &str) -> Result<(), DatabaseError> {
+        self.inner.update_sandbox_job_mode(id, mode).await
+    }
+
+    pub async fn get_sandbox_job_mode(&self, id: Uuid) -> Result<Option<String>, DatabaseError> {
+        self.inner.get_sandbox_job_mode(id).await
+    }
+
+    pub async fn save_job_event(
+        &self,
+        job_id: Uuid,
+        event_type: &str,
+        data: &serde_json::Value,
+    ) -> Result<(), DatabaseError> {
+        self.inner.save_job_event(job_id, event_type, data).await
+    }
+
+    pub async fn list_job_events(
+        &self,
+        job_id: Uuid,
+        limit: Option<i64>,
+    ) -> Result<Vec<crate::history::JobEventRecord>, DatabaseError> {
+        self.inner.list_job_events(job_id, limit).await
+    }
+
+    // === Job persistence (scheduler, worker) ===
+
+    pub async fn get_job(&self, id: Uuid) -> Result<Option<JobContext>, DatabaseError> {
+        self.inner.get_job(id).await
+    }
+
+    pub async fn save_job(&self, ctx: &JobContext) -> Result<(), DatabaseError> {
+        self.inner.save_job(ctx).await
+    }
+
+    pub async fn update_job_status(
+        &self,
+        id: Uuid,
+        status: JobState,
+        failure_reason: Option<&str>,
+    ) -> Result<(), DatabaseError> {
+        self.inner
+            .update_job_status(id, status, failure_reason)
+            .await
+    }
+
+    pub async fn mark_job_stuck(&self, id: Uuid) -> Result<(), DatabaseError> {
+        self.inner.mark_job_stuck(id).await
+    }
+
+    pub async fn list_agent_jobs(&self) -> Result<Vec<AgentJobRecord>, DatabaseError> {
+        self.inner.list_agent_jobs().await
+    }
+
+    pub async fn get_agent_job_failure_reason(
+        &self,
+        id: Uuid,
+    ) -> Result<Option<String>, DatabaseError> {
+        self.inner.get_agent_job_failure_reason(id).await
+    }
+
+    // === LLM call recording ===
+
+    pub async fn record_llm_call(&self, record: &LlmCallRecord<'_>) -> Result<Uuid, DatabaseError> {
+        self.inner.record_llm_call(record).await
+    }
+
+    pub async fn save_action(
+        &self,
+        job_id: Uuid,
+        action: &ActionRecord,
+    ) -> Result<(), DatabaseError> {
+        self.inner.save_action(job_id, action).await
+    }
+
+    pub async fn get_job_actions(&self, job_id: Uuid) -> Result<Vec<ActionRecord>, DatabaseError> {
+        self.inner.get_job_actions(job_id).await
+    }
+
+    // === Estimation ===
+
+    pub async fn save_estimation_snapshot(
+        &self,
+        job_id: Uuid,
+        category: &str,
+        tool_names: &[String],
+        estimated_cost: Decimal,
+        estimated_time_secs: i32,
+        estimated_value: Decimal,
+    ) -> Result<Uuid, DatabaseError> {
+        self.inner
+            .save_estimation_snapshot(
+                job_id,
+                category,
+                tool_names,
+                estimated_cost,
+                estimated_time_secs,
+                estimated_value,
+            )
+            .await
+    }
+
+    pub async fn update_estimation_actuals(
+        &self,
+        id: Uuid,
+        actual_cost: Decimal,
+        actual_time_secs: i32,
+        actual_value: Option<Decimal>,
+    ) -> Result<(), DatabaseError> {
+        self.inner
+            .update_estimation_actuals(id, actual_cost, actual_time_secs, actual_value)
+            .await
+    }
+
+    // === Conversations (admin context) ===
+
+    pub async fn add_conversation_message(
+        &self,
+        conversation_id: Uuid,
+        role: &str,
+        content: &str,
+    ) -> Result<Uuid, DatabaseError> {
+        self.inner
+            .add_conversation_message(conversation_id, role, content)
+            .await
+    }
+
+    pub async fn get_or_create_routine_conversation(
+        &self,
+        routine_id: Uuid,
+        routine_name: &str,
+        user_id: &str,
+    ) -> Result<Uuid, DatabaseError> {
+        self.inner
+            .get_or_create_routine_conversation(routine_id, routine_name, user_id)
+            .await
+    }
+
+    pub async fn get_or_create_heartbeat_conversation(
+        &self,
+        user_id: &str,
+    ) -> Result<Uuid, DatabaseError> {
+        self.inner
+            .get_or_create_heartbeat_conversation(user_id)
+            .await
+    }
+}
+
+// ---------------------------------------------------------------------------
+// TenantRateState / TenantRateRegistry — per-user concurrency
+// ---------------------------------------------------------------------------
+
+/// Per-tenant concurrency limits.
+pub struct TenantRateState {
+    /// Limits concurrent LLM calls for this user.
+    pub llm_semaphore: Arc<Semaphore>,
+    /// Limits concurrent jobs for this user.
+    pub job_semaphore: Arc<Semaphore>,
+}
+
+impl TenantRateState {
+    pub fn new(max_llm_concurrent: usize, max_job_concurrent: usize) -> Self {
+        Self {
+            llm_semaphore: Arc::new(Semaphore::new(max_llm_concurrent)),
+            job_semaphore: Arc::new(Semaphore::new(max_job_concurrent)),
+        }
+    }
+}
+
+/// Registry that lazily creates per-tenant rate state.
+///
+/// Uses `tokio::sync::RwLock<HashMap>` (consistent with the rest of the
+/// codebase — no DashMap dependency).
+pub struct TenantRateRegistry {
+    state: tokio::sync::RwLock<HashMap<String, Arc<TenantRateState>>>,
+    max_llm_concurrent: usize,
+    max_job_concurrent: usize,
+}
+
+impl TenantRateRegistry {
+    pub fn new(max_llm_concurrent: usize, max_job_concurrent: usize) -> Self {
+        Self {
+            state: tokio::sync::RwLock::new(HashMap::new()),
+            max_llm_concurrent,
+            max_job_concurrent,
+        }
+    }
+
+    /// Get or lazily create rate state for a user.
+    pub async fn get_or_create(&self, user_id: &str) -> Arc<TenantRateState> {
+        // Fast path: read lock
+        {
+            let map = self.state.read().await;
+            if let Some(s) = map.get(user_id) {
+                return Arc::clone(s);
+            }
+        }
+        // Slow path: write lock with double-check
+        let mut map = self.state.write().await;
+        if let Some(s) = map.get(user_id) {
+            return Arc::clone(s);
+        }
+        let s = Arc::new(TenantRateState::new(
+            self.max_llm_concurrent,
+            self.max_job_concurrent,
+        ));
+        map.insert(user_id.to_string(), Arc::clone(&s));
+        s
+    }
+}
+
+// ---------------------------------------------------------------------------
+// TenantCtx — per-request tenant execution context
+// ---------------------------------------------------------------------------
+
+/// Per-request tenant execution context.
+///
+/// Bundles a [`TenantScope`] (scoped DB access), workspace, cost guard,
+/// and per-tenant rate limiting. Constructed once per request via
+/// [`AgentDeps::tenant_ctx()`](crate::agent::AgentDeps::tenant_ctx).
+///
+/// `Clone + Send + Sync` — safe to store on `ChatDelegate` without lifetime issues.
+#[derive(Clone)]
+pub struct TenantCtx {
+    user_id: String,
+    store: Option<TenantScope>,
+    workspace: Option<Arc<Workspace>>,
+    cost_guard: Arc<CostGuard>,
+    rate: Arc<TenantRateState>,
+}
+
+impl TenantCtx {
+    pub fn new(
+        user_id: impl Into<String>,
+        store: Option<TenantScope>,
+        workspace: Option<Arc<Workspace>>,
+        cost_guard: Arc<CostGuard>,
+        rate: Arc<TenantRateState>,
+    ) -> Self {
+        Self {
+            user_id: user_id.into(),
+            store,
+            workspace,
+            cost_guard,
+            rate,
+        }
+    }
+
+    pub fn user_id(&self) -> &str {
+        &self.user_id
+    }
+
+    pub fn store(&self) -> Option<&TenantScope> {
+        self.store.as_ref()
+    }
+
+    pub fn workspace(&self) -> Option<&Arc<Workspace>> {
+        self.workspace.as_ref()
+    }
+
+    pub fn cost_guard(&self) -> &CostGuard {
+        &self.cost_guard
+    }
+
+    /// Check cost limits for this tenant (global + per-user).
+    pub async fn check_cost_allowed(&self) -> Result<(), CostLimitExceeded> {
+        self.cost_guard.check_allowed_for_user(&self.user_id).await
+    }
+
+    /// Record an LLM call for this tenant.
+    #[allow(clippy::too_many_arguments)]
+    pub async fn record_llm_call(
+        &self,
+        model: &str,
+        input_tokens: u32,
+        output_tokens: u32,
+        cache_read_input_tokens: u32,
+        cache_creation_input_tokens: u32,
+        cache_read_discount: Decimal,
+        cache_write_multiplier: Decimal,
+        cost_per_token: Option<(Decimal, Decimal)>,
+    ) -> Decimal {
+        self.cost_guard
+            .record_llm_call_for_user(
+                &self.user_id,
+                model,
+                input_tokens,
+                output_tokens,
+                cache_read_input_tokens,
+                cache_creation_input_tokens,
+                cache_read_discount,
+                cache_write_multiplier,
+                cost_per_token,
+            )
+            .await
+    }
+
+    /// Acquire an LLM concurrency permit for this tenant.
+    pub async fn acquire_llm_permit(&self) -> Result<SemaphorePermit<'_>, crate::error::Error> {
+        self.rate.llm_semaphore.acquire().await.map_err(|_| {
+            crate::error::Error::Config(crate::error::ConfigError::InvalidValue {
+                key: "llm_semaphore".to_string(),
+                message: "semaphore closed".to_string(),
+            })
+        })
+    }
+}
+
+// ---------------------------------------------------------------------------
+// Tests
+// ---------------------------------------------------------------------------
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[tokio::test]
+    async fn test_rate_registry_returns_same_state_for_same_user() {
+        let registry = TenantRateRegistry::new(4, 3);
+        let a1 = registry.get_or_create("alice").await;
+        let a2 = registry.get_or_create("alice").await;
+        assert!(Arc::ptr_eq(&a1, &a2));
+    }
+
+    #[tokio::test]
+    async fn test_rate_registry_different_users_get_different_state() {
+        let registry = TenantRateRegistry::new(4, 3);
+        let alice = registry.get_or_create("alice").await;
+        let bob = registry.get_or_create("bob").await;
+        assert!(!Arc::ptr_eq(&alice, &bob));
+    }
+}

src/testing/mod.rs

@@ -532,6 +532,7 @@ impl TestHarnessBuilder {
         let cost_guard = Arc::new(CostGuard::new(CostGuardConfig {
             max_cost_per_day_cents: None,
             max_actions_per_hour: None,
+            max_cost_per_user_per_day_cents: None,
         }));
 
         let channel = if self.stub_channel {
@@ -564,6 +565,7 @@ impl TestHarnessBuilder {
             sandbox_readiness: crate::agent::routine_engine::SandboxReadiness::DisabledByConfig,
             builder: None,
             llm_backend: "nearai".to_string(),
+            tenant_rates: std::sync::Arc::new(crate::tenant::TenantRateRegistry::new(4, 3)),
         };
 
         TestHarness {

src/tools/builtin/extension_tools.rs

@@ -31,8 +31,11 @@ impl Tool for ToolSearchTool {
 
     fn description(&self) -> &str {
         "Search for available extensions to add new capabilities. Extensions include \
-         channels (Telegram, Slack, Discord — for messaging), tools, and MCP servers. \
+         channels (Telegram, Slack, Discord — connect messaging platforms so IronClaw can \
-         Use discover:true to search online if the built-in registry has no results."
+         receive and reply there), tools, and MCP servers. Use `tool_install` and \
+         `tool_activate` to install and enable channels; use the `message` tool for proactive \
+         outbound sends. Use discover:true to search online if the built-in registry has no \
+         results."
     }
 
     fn parameters_schema(&self) -> serde_json::Value {
@@ -634,6 +637,17 @@ mod tests {
         assert!(schema["properties"].get("query").is_some());
     }
 
+    #[test]
+    fn test_tool_search_description_clarifies_channel_setup_vs_sending() {
+        let tool = ToolSearchTool {
+            manager: test_manager_stub(),
+        };
+
+        let description = tool.description();
+        assert!(description.contains("Use `tool_install` and `tool_activate`"));
+        assert!(description.contains("use the `message` tool for proactive outbound sends"));
+    }
+
     #[test]
     fn test_tool_install_schema() {
         use crate::tools::tool::ApprovalRequirement;

src/tools/builtin/message.rs

@@ -181,11 +181,15 @@ impl Tool for MessageTool {
     }
 
     fn description(&self) -> &str {
-        "Send a message to a channel. If channel/target omitted, uses the current conversation's \
+        "Send a proactive message to a channel. Use normal assistant output to reply in the \
-         channel and sender/group. Use to proactively message users on any connected channel. \
+         active conversation; use this tool for proactive notifications, routine/background \
+         follow-ups, attachments, or sending to a different channel/recipient. If channel/target \
+         are omitted, reuses the current conversation's channel and sender/group when available. \
+         If you provide `target` without `channel` and no scoped channel can be resolved, the \
+         message may be broadcast across connected channels instead of sent to just one. \
          Supports file attachments: first download the file with the http tool using save_to \
-         (e.g., http GET https://picsum.photos/800/600 save_to=/tmp/photo.jpg), then pass \
+         (e.g., http GET https://picsum.photos/800/600 save_to=/tmp/photo.jpg), then pass the \
-         the file path in the attachments array. Images are sent as photos on Telegram. \
+         file path in the attachments array. Images are sent as photos on Telegram. \
          - Signal: target accepts E.164 (+1234567890) or group ID \
          - Telegram: target accepts username or chat ID \
          - Slack: target accepts channel (#general) or user ID"
@@ -451,7 +455,11 @@ mod tests {
     #[test]
     fn message_tool_description() {
         let tool = MessageTool::new(Arc::new(ChannelManager::new()));
-        assert!(!tool.description().is_empty());
+        let description = tool.description();
+        assert!(!description.is_empty());
+        assert!(description.contains("Use normal assistant output to reply"));
+        assert!(description.contains("proactive notifications"));
+        assert!(description.contains("provide `target` without `channel`"));
     }
 
     #[test]

src/tools/builtin/routine.rs

@@ -915,7 +915,7 @@ fn parse_routine_create_request(
 fn build_routine_trigger(trigger: &NormalizedTriggerRequest) -> Trigger {
     match trigger {
         NormalizedTriggerRequest::Cron { schedule, timezone } => Trigger::Cron {
-            schedule: schedule.clone(),
+            schedule: normalize_cron_expression(schedule),
             timezone: timezone.clone(),
         },
         NormalizedTriggerRequest::Manual => Trigger::Manual,
@@ -1836,6 +1836,20 @@ mod tests {
         assert_eq!(parsed.cooldown_secs, 30);
     }
 
+    #[test]
+    fn build_routine_trigger_normalizes_cron_schedule() {
+        let trigger = build_routine_trigger(&NormalizedTriggerRequest::Cron {
+            schedule: "0 0 9 * * MON-FRI".to_string(),
+            timezone: Some("UTC".to_string()),
+        });
+
+        assert!(matches!(
+            trigger,
+            Trigger::Cron { schedule, timezone }
+                if schedule == "0 0 9 * * MON-FRI *" && timezone.as_deref() == Some("UTC")
+        ));
+    }
+
     #[test]
     fn parses_grouped_message_event_with_tools() {
         let params = serde_json::json!({

src/worker/job.rs

@@ -20,7 +20,6 @@ use crate::agent::scheduler::WorkerMessage;
 use crate::agent::task::TaskOutput;
 use crate::channels::web::types::ToolDecisionDto;
 use crate::context::{ContextManager, JobState};
-use crate::db::Database;
 use crate::error::Error;
 use crate::hooks::HookRegistry;
 use crate::llm::{
@@ -28,6 +27,7 @@ use crate::llm::{
     ToolSelection,
 };
 use crate::safety::SafetyLayer;
+use crate::tenant::AdminScope;
 use crate::tools::execute::process_tool_result;
 use crate::tools::rate_limiter::RateLimitResult;
 use crate::tools::{
@@ -45,7 +45,7 @@ pub struct WorkerDeps {
     pub llm: Arc<dyn LlmProvider>,
     pub safety: Arc<SafetyLayer>,
     pub tools: Arc<ToolRegistry>,
-    pub store: Option<Arc<dyn Database>>,
+    pub store: Option<AdminScope>,
     pub hooks: Arc<HookRegistry>,
     pub timeout: Duration,
     pub use_planning: bool,
@@ -94,7 +94,7 @@ impl Worker {
         &self.deps.tools
     }
 
-    fn store(&self) -> Option<&Arc<dyn Database>> {
+    fn store(&self) -> Option<&AdminScope> {
         self.deps.store.as_ref()
     }
 
@@ -1158,6 +1158,7 @@ impl<'a> JobDelegate<'a> {
         Ok(crate::llm::RespondOutput {
             result: RespondResult::Text(String::new()),
             usage: crate::llm::TokenUsage::default(),
+            finish_reason: crate::llm::FinishReason::Stop,
         })
     }
 }
@@ -1283,6 +1284,7 @@ impl<'a> LoopDelegate for JobDelegate<'a> {
                         content: reasoning_text,
                     },
                     usage: crate::llm::TokenUsage::default(),
+                    finish_reason: crate::llm::FinishReason::ToolUse,
                 });
             }
             Ok(_) => {} // empty selections, fall through

src/workspace/mod.rs

@@ -149,6 +149,7 @@ fn reject_if_injected(path: &str, content: &str) -> Result<(), WorkspaceError> {
 ///
 /// Allows Workspace to work with either a PostgreSQL `Repository` (the original
 /// path) or any `Database` trait implementation (e.g. libSQL backend).
+#[derive(Clone)]
 enum WorkspaceStorage {
     /// PostgreSQL-backed repository (uses connection pool directly).
     #[cfg(feature = "postgres")]
@@ -576,6 +577,60 @@ impl Workspace {
         self
     }
 
+    /// Clone the workspace configuration for a different primary user scope.
+    ///
+    /// This preserves search config, embeddings, shared read scopes, memory
+    /// layers, and privacy classifier while switching the primary read/write
+    /// scope to `user_id`.
+    pub fn scoped_to_user(&self, user_id: impl Into<String>) -> Self {
+        let user_id = user_id.into();
+
+        let mut memory_layers = self.memory_layers.clone();
+        for layer in &mut memory_layers {
+            if layer.sensitivity == crate::workspace::layer::LayerSensitivity::Private
+                && layer.scope == self.user_id
+            {
+                layer.scope = user_id.clone();
+            }
+        }
+
+        let mut read_user_ids = vec![user_id.clone()];
+        for scope in &self.read_user_ids {
+            if scope != &self.user_id && !read_user_ids.contains(scope) {
+                read_user_ids.push(scope.clone());
+            }
+        }
+        for scope in crate::workspace::layer::MemoryLayer::read_scopes(&memory_layers) {
+            if !read_user_ids.contains(&scope) {
+                read_user_ids.push(scope);
+            }
+        }
+
+        let preserve_flags = user_id == self.user_id;
+        Self {
+            user_id,
+            read_user_ids,
+            agent_id: self.agent_id,
+            storage: self.storage.clone(),
+            embeddings: self.embeddings.clone(),
+            bootstrap_pending: std::sync::atomic::AtomicBool::new(if preserve_flags {
+                self.bootstrap_pending
+                    .load(std::sync::atomic::Ordering::Acquire)
+            } else {
+                false
+            }),
+            bootstrap_completed: std::sync::atomic::AtomicBool::new(if preserve_flags {
+                self.bootstrap_completed
+                    .load(std::sync::atomic::Ordering::Acquire)
+            } else {
+                false
+            }),
+            search_defaults: self.search_defaults.clone(),
+            memory_layers,
+            privacy_classifier: self.privacy_classifier.clone(),
+        }
+    }
+
     /// Get the user ID (primary scope for writes).
     pub fn user_id(&self) -> &str {
         &self.user_id

src/workspace/repository.rs

@@ -15,6 +15,7 @@ use crate::workspace::document::{MemoryChunk, MemoryDocument, WorkspaceEntry};
 use crate::workspace::search::{RankedResult, SearchConfig, SearchResult, fuse_results};
 
 /// Database repository for workspace operations.
+#[derive(Clone)]
 pub struct Repository {
     pool: Pool,
 }

tests/e2e/scenarios/test_telegram_hot_activation.py

@@ -253,6 +253,6 @@ async def test_telegram_hot_activation_transitions_installed_to_active(page):
     assert await card.locator(SEL["ext_pairing_label"]).count() == 0
 
     assert captured_setup_payloads == [
-        {"secrets": {"telegram_bot_token": "123456789:ABCdefGhI"}},
+        {"secrets": {"telegram_bot_token": "123456789:ABCdefGhI"}, "fields": {}},
-        {"secrets": {}},
+        {"secrets": {}, "fields": {}},
     ]

tests/e2e_advanced_traces.rs

@@ -587,6 +587,7 @@ mod advanced {
     async fn mcp_extension_lifecycle() {
         use crate::support::mock_mcp_server::{MockToolResponse, start_mock_mcp_server};
         use ironclaw::extensions::{AuthHint, ExtensionKind, ExtensionSource, RegistryEntry};
+        const TEST_USER_ID: &str = "test-user";
 
         // 1. Start mock MCP server with pre-configured tool responses.
         let mock_server = start_mock_mcp_server(vec![
@@ -654,14 +655,14 @@ mod advanced {
         ext_mgr
             .secrets()
             .create(
-                "default",
+                TEST_USER_ID,
                 ironclaw::secrets::CreateSecretParams::new(secret_name, "mock-access-token")
                     .with_provider("mcp:mock-notion".to_string()),
             )
             .await
             .expect("failed to inject test token");
 
-        let activate_result = ext_mgr.activate("mock-notion", "default").await;
+        let activate_result = ext_mgr.activate("mock-notion", TEST_USER_ID).await;
         assert!(
             activate_result.is_ok(),
             "activation failed: {:?}",

tests/e2e_builtin_tool_coverage.rs

@@ -13,7 +13,7 @@ mod tests {
     use ironclaw::agent::routine::{RoutineAction, Trigger};
 
     use crate::support::test_rig::TestRigBuilder;
-    use crate::support::trace_llm::LlmTrace;
+    use crate::support::trace_llm::{LlmTrace, TraceResponse, TraceStep, TraceToolCall, TraceTurn};
 
     // -----------------------------------------------------------------------
     // Test 1: time_parse_and_diff
@@ -439,7 +439,7 @@ mod tests {
 
         match &routine.trigger {
             Trigger::Cron { schedule, timezone } => {
-                assert_eq!(schedule, "0 0 9 * * MON-FRI");
+                assert_eq!(schedule, "0 0 9 * * MON-FRI *");
                 assert_eq!(timezone.as_deref(), Some("UTC"));
             }
             other => panic!("expected cron trigger, got {other:?}"),
@@ -838,4 +838,112 @@ mod tests {
 
         rig.shutdown();
     }
+
+    #[tokio::test]
+    async fn tool_info_clarifies_message_and_channel_setup_roles() {
+        let trace = LlmTrace::new(
+            "test-tool-info-channel-message-clarity",
+            vec![TraceTurn {
+                user_input: "How do message and channels differ?".to_string(),
+                steps: vec![
+                    TraceStep {
+                        request_hint: None,
+                        response: TraceResponse::ToolCalls {
+                            tool_calls: vec![TraceToolCall {
+                                id: "call_tool_info_message".to_string(),
+                                name: "tool_info".to_string(),
+                                arguments: serde_json::json!({"name": "message"}),
+                            }],
+                            input_tokens: 100,
+                            output_tokens: 20,
+                        },
+                        expected_tool_results: Vec::new(),
+                    },
+                    TraceStep {
+                        request_hint: None,
+                        response: TraceResponse::ToolCalls {
+                            tool_calls: vec![TraceToolCall {
+                                id: "call_tool_info_tool_search".to_string(),
+                                name: "tool_info".to_string(),
+                                arguments: serde_json::json!({"name": "tool_search"}),
+                            }],
+                            input_tokens: 140,
+                            output_tokens: 20,
+                        },
+                        expected_tool_results: Vec::new(),
+                    },
+                    TraceStep {
+                        request_hint: None,
+                        response: TraceResponse::Text {
+                            content: "I checked both tool descriptions.".to_string(),
+                            input_tokens: 220,
+                            output_tokens: 30,
+                        },
+                        expected_tool_results: Vec::new(),
+                    },
+                ],
+                expects: Default::default(),
+            }],
+        );
+
+        let rig = TestRigBuilder::new()
+            .with_trace(trace.clone())
+            .with_auto_approve_tools(true)
+            .build()
+            .await;
+
+        rig.send_message("How do message and channels differ?")
+            .await;
+        let responses = rig.wait_for_responses(1, Duration::from_secs(15)).await;
+
+        rig.verify_trace_expects(&trace, &responses);
+
+        let results = rig.tool_results();
+        let info_results: Vec<_> = results.iter().filter(|(n, _)| n == "tool_info").collect();
+        assert_eq!(info_results.len(), 2, "Expected two tool_info results");
+
+        let info_json: Vec<serde_json::Value> = info_results
+            .iter()
+            .map(|(_, preview)| {
+                serde_json::from_str(preview)
+                    .expect("tool_info result preview should be valid JSON")
+            })
+            .collect();
+
+        let message_json = info_json
+            .iter()
+            .find(|info| info["name"] == "message")
+            .expect("tool_info result should contain 'message'");
+        let message_description = message_json["description"]
+            .as_str()
+            .expect("message description should be a string");
+        assert!(
+            message_description.contains("Use normal assistant output to reply"),
+            "message description should distinguish normal replies: {message_description}"
+        );
+        assert!(
+            message_description.contains("proactive notifications"),
+            "message description should describe proactive sends: {message_description}"
+        );
+
+        let tool_search_json = info_json
+            .iter()
+            .find(|info| info["name"] == "tool_search")
+            .expect("tool_info result should contain 'tool_search'");
+        let tool_search_description = tool_search_json["description"]
+            .as_str()
+            .expect("tool_search description should be a string");
+        assert!(
+            tool_search_description.contains("`tool_install`")
+                && tool_search_description.contains("`tool_activate`"),
+            "tool_search description should describe setup/activation via tool_install and \
+             tool_activate: {tool_search_description}"
+        );
+        assert!(
+            tool_search_description.contains("use the `message` tool for proactive outbound sends"),
+            "tool_search description should point outbound sends to message: {tool_search_description}"
+        );
+
+        rig.shutdown();
+    }
 }

tests/e2e_routine_heartbeat.rs

@@ -337,14 +337,14 @@ mod tests {
             SchedulerDeps {
                 tools: registry.clone(),
                 extension_manager: extension_manager.clone(),
-                store: Some(db.clone()),
+                store: Some(ironclaw::tenant::AdminScope::new(db.clone())),
                 hooks: Arc::new(HookRegistry::new()),
             },
         ));
 
         Arc::new(RoutineEngine::new(
             RoutineConfig::default(),
-            db,
+            ironclaw::tenant::AdminScope::new(db),
             llm,
             ws,
             notify_tx,
@@ -448,7 +448,7 @@ mod tests {
 
         let engine = Arc::new(RoutineEngine::new(
             RoutineConfig::default(),
-            db.clone(),
+            ironclaw::tenant::AdminScope::new(db.clone()),
             llm,
             ws,
             notify_tx,
@@ -527,7 +527,7 @@ mod tests {
 
         let engine = Arc::new(RoutineEngine::new(
             RoutineConfig::default(),
-            db.clone(),
+            ironclaw::tenant::AdminScope::new(db.clone()),
             llm,
             ws,
             notify_tx,
@@ -614,7 +614,7 @@ mod tests {
 
         let engine = Arc::new(RoutineEngine::new(
             RoutineConfig::default(),
-            db.clone(),
+            ironclaw::tenant::AdminScope::new(db.clone()),
             llm,
             ws,
             notify_tx,
@@ -723,7 +723,7 @@ mod tests {
 
         let engine = Arc::new(RoutineEngine::new(
             RoutineConfig::default(),
-            db.clone(),
+            ironclaw::tenant::AdminScope::new(db.clone()),
             llm,
             ws,
             notify_tx,
@@ -866,7 +866,7 @@ mod tests {
 
         let engine = Arc::new(RoutineEngine::new(
             RoutineConfig::default(),
-            db.clone(),
+            ironclaw::tenant::AdminScope::new(db.clone()),
             llm,
             ws,
             notify_tx,
@@ -1049,7 +1049,7 @@ mod tests {
 
         let engine = Arc::new(RoutineEngine::new(
             RoutineConfig::default(),
-            Arc::clone(&db),
+            ironclaw::tenant::AdminScope::new(Arc::clone(&db)),
             llm,
             ws,
             notify_tx,
@@ -1171,7 +1171,7 @@ mod tests {
 
         let engine = Arc::new(RoutineEngine::new(
             RoutineConfig::default(),
-            db.clone(),
+            ironclaw::tenant::AdminScope::new(db.clone()),
             llm,
             ws,
             notify_tx,
@@ -1279,7 +1279,7 @@ mod tests {
 
         let engine = Arc::new(RoutineEngine::new(
             config,
-            db.clone(),
+            ironclaw::tenant::AdminScope::new(db.clone()),
             llm,
             ws,
             notify_tx,

tests/e2e_telegram_message_routing.rs

@@ -201,6 +201,7 @@ mod tests {
             sandbox_readiness: ironclaw::agent::SandboxReadiness::DisabledByConfig,
             builder: None,
             llm_backend: "nearai".to_string(),
+            tenant_rates: std::sync::Arc::new(ironclaw::tenant::TenantRateRegistry::new(4, 3)),
         };
 
         let gateway = Arc::new(TestChannel::new());

tests/e2e_workspace_coverage.rs

@@ -12,6 +12,7 @@ mod tests {
 
     use crate::support::test_rig::TestRigBuilder;
     use crate::support::trace_llm::LlmTrace;
+    use ironclaw::workspace::Workspace;
 
     // -----------------------------------------------------------------------
     // Test 1: write_chunk_search
@@ -268,6 +269,7 @@ mod tests {
 
     #[tokio::test]
     async fn identity_in_system_prompt() {
+        const TEST_USER_ID: &str = "test-user";
         let trace = LlmTrace::from_file(concat!(
             env!("CARGO_MANIFEST_DIR"),
             "/tests/fixtures/llm_traces/workspace/identity_prompt.json"
@@ -280,7 +282,7 @@ mod tests {
             .await;
 
         // Seed an IDENTITY.md so the system prompt has real content to inject.
-        let ws = rig.workspace().expect("workspace must be available");
+        let ws = Workspace::new_with_db(TEST_USER_ID, rig.database().clone());
         ws.write(
             "IDENTITY.md",
             "I am TestBot, a helpful testing assistant created for E2E verification.",

tests/multi_tenant_system_prompt.rs

@@ -1,10 +1,10 @@
-//! Tests proving that multi-tenant system prompts are broken.
+//! Regression tests for multi-tenant system prompts.
 //!
-//! Bug: In multi-tenant mode, the agent loop uses `self.workspace()` which
+//! The agent must build the conversational system prompt from a workspace
-//! returns a single shared workspace (user_id="default"). Identity files
+//! scoped to the incoming message's user, not from the shared owner-scope
-//! (IDENTITY.md, SOUL.md, USER.md) seeded under per-user IDs ("alice",
+//! workspace created at startup. Otherwise per-user identity files
-//! "bob") are invisible to this workspace, so the system prompt is
+//! (IDENTITY.md, SOUL.md, USER.md) become invisible and different users can
-//! empty/wrong.
+//! see the same owner-scoped prompt.
 //!
 //! These tests:
 //! 1. Seed identity files for two users (alice, bob) in the database
@@ -13,7 +13,7 @@
 //!    correct user's identity
 //! 4. Verify user A's identity doesn't leak into user B's prompt
 //!
-//! All tests are expected to FAIL until the bug is fixed.
+//! These tests ensure each user's identity is isolated correctly.
 
 #[cfg(feature = "libsql")]
 mod support;
@@ -237,4 +237,47 @@ mod tests {
 
         rig.shutdown();
     }
+
+    #[tokio::test]
+    async fn telegram_system_prompt_clarifies_reply_vs_proactive_message_tool() {
+        let trace = simple_trace(1);
+        let rig = TestRigBuilder::new().with_trace(trace).build().await;
+
+        let msg = IncomingMessage::new("telegram", "telegram-user", "Hello there");
+        rig.send_incoming(msg).await;
+        let _responses = rig.wait_for_responses(1, TIMEOUT).await;
+
+        let requests = rig.captured_llm_requests();
+        let system_prompt =
+            extract_system_prompt(&requests).expect("Expected a system prompt in the LLM request");
+
+        assert!(
+            system_prompt.contains("Channels are not separate send-message tools"),
+            "System prompt should describe channels as setup/integration surfaces.\n\
+             Actual system prompt:\n{system_prompt}"
+        );
+        assert!(
+            system_prompt
+                .contains("use normal assistant output to reply in the current conversation"),
+            "System prompt should route ordinary replies through normal assistant output.\n\
+             Actual system prompt:\n{system_prompt}"
+        );
+        assert!(
+            system_prompt.contains("respond normally without calling `message`"),
+            "System prompt should say normal replies do not use the message tool.\n\
+             Actual system prompt:\n{system_prompt}"
+        );
+        assert!(
+            system_prompt.contains("proactive follow-up in the current conversation"),
+            "System prompt should reserve omitted channel/target for proactive follow-ups.\n\
+             Actual system prompt:\n{system_prompt}"
+        );
+        assert!(
+            !system_prompt.contains("omit 'target' to send here"),
+            "System prompt should not imply the message tool is the default way to reply \
+             in-thread.\nActual system prompt:\n{system_prompt}"
+        );
+
+        rig.shutdown();
+    }
 }

tests/support/gateway_workflow_harness.rs

@@ -266,6 +266,7 @@ impl GatewayWorkflowHarness {
                 sandbox_readiness: ironclaw::agent::SandboxReadiness::DisabledByConfig,
                 builder: None,
                 llm_backend: "nearai".to_string(),
+                tenant_rates: std::sync::Arc::new(ironclaw::tenant::TenantRateRegistry::new(4, 3)),
             },
             channels,
             None,

tests/support/test_rig.rs

@@ -642,7 +642,7 @@ impl TestRigBuilder {
                 let (notify_tx, _notify_rx) = tokio::sync::mpsc::channel(16);
                 let engine = Arc::new(RoutineEngine::new(
                     routine_config,
-                    Arc::clone(db_arc),
+                    ironclaw::tenant::AdminScope::new(Arc::clone(db_arc)),
                     components.llm.clone(),
                     Arc::clone(ws),
                     notify_tx,
@@ -762,6 +762,7 @@ impl TestRigBuilder {
             sandbox_readiness: ironclaw::agent::SandboxReadiness::Available, // tests don't use real Docker
             builder: None,
             llm_backend: "nearai".to_string(),
+            tenant_rates: std::sync::Arc::new(ironclaw::tenant::TenantRateRegistry::new(4, 3)),
         };
 
         // 7. Create TestChannel and ChannelManager.