diff --git a/CHANGELOG.md b/CHANGELOG.md
index 6aad4993..9acc56ad 100644
--- a/CHANGELOG.md
+++ b/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
diff --git a/Cargo.lock b/Cargo.lock
index 27c258c1..c3747590 100644
--- a/Cargo.lock
+++ b/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]]
diff --git a/Cargo.toml b/Cargo.toml
index 395e42d3..41895b16 100644
--- a/Cargo.toml
+++ b/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"
 
diff --git a/crates/ironclaw_common/Cargo.toml b/crates/ironclaw_common/Cargo.toml
index 353ab747..6e7db5a4 100644
--- a/crates/ironclaw_common/Cargo.toml
+++ b/crates/ironclaw_common/Cargo.toml
@@ -8,7 +8,6 @@ authors = ["NEAR AI <support@near.ai>"]
 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
diff --git a/crates/ironclaw_safety/Cargo.toml b/crates/ironclaw_safety/Cargo.toml
index d12aa909..38b8718a 100644
--- a/crates/ironclaw_safety/Cargo.toml
+++ b/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 <support@near.ai>"]
 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
diff --git a/registry/channels/feishu.json b/registry/channels/feishu.json
index 66cecf1d..a7530943 100644
--- a/registry/channels/feishu.json
+++ b/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",
-      "url": "https://github.com/nearai/ironclaw/releases/download/v0.19.0/channel-feishu-0.1.1-wasm32-wasip2.tar.gz"
+      "sha256": "a66ff0dafb67d2216d8161bb7e96e724a94acb0ab993b85d2782d30412f8fe94",
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/channel-feishu-0.1.3-wasm32-wasip2.tar.gz"
     }
   },
   "auth_summary": {
diff --git a/registry/channels/telegram.json b/registry/channels/telegram.json
index 85d793ed..52f66ce3 100644
--- a/registry/channels/telegram.json
+++ b/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",
-      "sha256": "a7cb300ec1c946831cfceaa95c1dc8f30d0f42a3924f3cb5de8098821573f4b8"
+      "url": "https://github.com/nearai/ironclaw/releases/download/v0.20.0/channel-telegram-0.2.5-wasm32-wasip2.tar.gz",
+      "sha256": "1ef20a538f55b379e049356e4d6758006251846bc3365ceaa1c87eba8379a329"
     }
   },
   "auth_summary": {
diff --git a/registry/tools/github.json b/registry/tools/github.json
index e760c4df..bb351259 100644
--- a/registry/tools/github.json
+++ b/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",
-      "sha256": "92c530b3ad172e2372d819744b5233f1d8f65768e26eb5a6c213eba3ce1de758"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-github-0.2.2-wasm32-wasip2.tar.gz",
+      "sha256": "70b55af593193d8fa495c0f702ea23284d83a624124f8a5f7564916ec5032c3f"
     }
   },
   "auth_summary": {
diff --git a/registry/tools/gmail.json b/registry/tools/gmail.json
index 08913ce6..c4772129 100644
--- a/registry/tools/gmail.json
+++ b/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",
-      "sha256": "ee9574e02e92bc1d481f1310eb88afd99ee52bf6971074ab33bd76bf99b34b1d"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-gmail-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "79025b40ee70ce1120acc4320bae50da095d7afb0ef67bd56d99b064b72ea779"
     }
   },
   "auth_summary": {
diff --git a/registry/tools/google-calendar.json b/registry/tools/google-calendar.json
index c43112d3..73065a67 100644
--- a/registry/tools/google-calendar.json
+++ b/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",
-      "sha256": "2fa47150ea222e787c122182ad6f4dfa2ffaf5fe490d05e8de887a76445f8d2d"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-google-calendar-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "86bcc075010b08f5ab2f98f504cec1c6c9e0ca144857d185cbecf72a11f504bf"
     }
   },
   "auth_summary": {
diff --git a/registry/tools/google-docs.json b/registry/tools/google-docs.json
index 9f1ab133..02cc94fe 100644
--- a/registry/tools/google-docs.json
+++ b/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",
-      "sha256": "40e134a1c1564f832ca861c3396895d4e33ec67b99313fc1f97baf8d971423a9"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-google-docs-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "39d476029764949498a53a6a223f9952b5f4df151be7b8b19bf3fe4d401a57cd"
     }
   },
   "auth_summary": {
diff --git a/registry/tools/google-drive.json b/registry/tools/google-drive.json
index 9766e555..719690f7 100644
--- a/registry/tools/google-drive.json
+++ b/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",
-      "sha256": "002a341a1d58125563a7c69561b26fbc2629b04ea723cade744102bdc0fbb71f"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-google-drive-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "6e9a700fab93865c852af718666af64c5b534ad6a419fb4b736e07740188f494"
     }
   },
   "auth_summary": {
diff --git a/registry/tools/google-sheets.json b/registry/tools/google-sheets.json
index b63265e1..09aae574 100644
--- a/registry/tools/google-sheets.json
+++ b/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",
-      "sha256": "8aa2c9d52f033edea3a6c2311b0ec694ccb6d0a54ef07e94d72bf8be1ce8009a"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-google-sheets-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "1f8c381799a916be83263cac9d497d52946e21b1b588592a3a42ca94a73b7051"
     }
   },
   "auth_summary": {
diff --git a/registry/tools/google-slides.json b/registry/tools/google-slides.json
index 54187531..64bc0e45 100644
--- a/registry/tools/google-slides.json
+++ b/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",
-      "sha256": "e931a97d4fd0b0b938e464dc7c7f2be6ea6b4d1508f5ea3cd931d44db23f05f5"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-google-slides-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "e2528be5da02f1b8cfc8ee9b0cdd849516c53d412e2f75c6175b3bded7f512cb"
     }
   },
   "auth_summary": {
diff --git a/registry/tools/llm-context.json b/registry/tools/llm-context.json
index e4e9808c..422f2e18 100644
--- a/registry/tools/llm-context.json
+++ b/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",
-      "sha256": "d9ced2b1226b879135891e0ee40e072c7c95412e1b2462925a23853e1f92497e"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-llm-context-0.1.1-wasm32-wasip2.tar.gz",
+      "sha256": "9b19e2fd05dbbbe3c8bd55309a91db09124e8415eb0f767828b6e10b55771e63"
     }
   },
   "auth_summary": {
diff --git a/registry/tools/slack.json b/registry/tools/slack.json
index 8e1df989..236062a4 100644
--- a/registry/tools/slack.json
+++ b/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",
-      "sha256": "ccfb0415d7a04f9497726c712d15216de36e86f498b849101283c017f5ab4efb"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-slack-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "927519e5b7734beeb022d3b8bbd152e0e6b9f67c9452a8ad47809d3c4221a137"
     }
   },
   "auth_summary": {
diff --git a/registry/tools/telegram.json b/registry/tools/telegram.json
index 12e58c68..e684ca94 100644
--- a/registry/tools/telegram.json
+++ b/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",
-      "sha256": "c17065ca41fae5f2a7c43b36144686718cd310a2f22442313bb1aa82bbad0ae4"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-telegram-0.2.1-wasm32-wasip2.tar.gz",
+      "sha256": "1e57d0755fc9c7b3ec013d079f30168898b484a6919f9edd105f0cd80131c1cd"
     }
   },
   "auth_summary": {
diff --git a/registry/tools/web-search.json b/registry/tools/web-search.json
index 5c1dedef..014466af 100644
--- a/registry/tools/web-search.json
+++ b/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",
-      "sha256": "bad275ca4ec314adea5241d6b92c44ccf9cebcbca8e30ba2493cc0bcb4b57218"
+      "url": "https://github.com/nearai/ironclaw/releases/download/ironclaw-v0.22.0/tool-web-search-0.2.2-wasm32-wasip2.tar.gz",
+      "sha256": "47382b50c1ea7525b20d59dc02fab04e336d018665826c2f24710bdf460779ae"
     }
   },
   "auth_summary": {
diff --git a/release-plz.toml b/release-plz.toml
index b003952d..e8e0670f 100644
--- a/release-plz.toml
+++ b/release-plz.toml
@@ -1,7 +1,2 @@
 [workspace]
 git_release_enable = false
-
-[[package]]
-name = "ironclaw_safety"
-publish = false
-release = false
diff --git a/src/channels/relay/client.rs b/src/channels/relay/client.rs
index 81fbb56c..b67f2c5e 100644
--- a/src/channels/relay/client.rs
+++ b/src/channels/relay/client.rs
@@ -122,18 +122,32 @@ impl RelayClient {
     /// instance_url in chat-api. IronClaw only passes an optional CSRF nonce
     /// for validating the callback — no URLs.
     pub async fn initiate_oauth(&self, state_nonce: Option<&str>) -> Result<String, RelayError> {
+        let url = format!("{}/oauth/slack/auth", self.base_url);
+        tracing::debug!(relay_url = %url, "RelayClient::initiate_oauth: sending request");
         let mut query: Vec<(&str, &str)> = vec![];
         if let Some(nonce) = state_nonce {
             query.push(("state_nonce", nonce));
         }
         let resp = self
             .http
-            .get(format!("{}/oauth/slack/auth", self.base_url))
+            .get(&url)
             .bearer_auth(self.api_key.expose_secret())
             .query(&query)
             .send()
             .await
-            .map_err(|e| RelayError::Network(e.to_string()))?;
+            .map_err(|e| {
+                tracing::warn!(
+                    relay_url = %url,
+                    error = %e,
+                    "RelayClient::initiate_oauth: network request failed"
+                );
+                RelayError::Network(e.to_string())
+            })?;
+        tracing::debug!(
+            relay_url = %url,
+            status = %resp.status(),
+            "RelayClient::initiate_oauth: received response"
+        );
 
         let status = resp.status();
         if status.is_redirection() {
@@ -224,20 +238,39 @@ impl RelayClient {
         method: &str,
         body: serde_json::Value,
     ) -> Result<serde_json::Value, RelayError> {
+        let url = format!("{}/proxy/{}/{}", self.base_url, provider, method);
+        tracing::debug!(
+            relay_url = %url,
+            provider = %provider,
+            method = %method,
+            "RelayClient::proxy_provider: sending request"
+        );
         let query: Vec<(&str, &str)> = vec![("team_id", team_id)];
         let resp = self
             .http
-            .post(format!("{}/proxy/{}/{}", self.base_url, provider, method))
+            .post(&url)
             .bearer_auth(self.api_key.expose_secret())
             .query(&query)
             .json(&body)
             .send()
             .await
-            .map_err(|e| RelayError::Network(e.to_string()))?;
+            .map_err(|e| {
+                tracing::warn!(
+                    relay_url = %url,
+                    error = %e,
+                    "RelayClient::proxy_provider: network request failed"
+                );
+                RelayError::Network(e.to_string())
+            })?;
 
         if !resp.status().is_success() {
             let status = resp.status().as_u16();
             let body = resp.text().await.unwrap_or_default();
+            tracing::warn!(
+                relay_url = %url,
+                status = status,
+                "RelayClient::proxy_provider: channel-relay returned error"
+            );
             return Err(RelayError::Api {
                 status,
                 message: body,
@@ -255,23 +288,45 @@ impl RelayClient {
     /// 32-byte secret. Called once at activation time; the result is cached in the
     /// extension manager so subsequent calls to `relay_signing_secret()` use it.
     pub async fn get_signing_secret(&self, team_id: &str) -> Result<Vec<u8>, RelayError> {
+        let url = format!("{}/relay/signing-secret", self.base_url);
+        tracing::debug!(
+            relay_url = %url,
+            "RelayClient::get_signing_secret: fetching signing secret"
+        );
         let resp = self
             .http
-            .get(format!("{}/relay/signing-secret", self.base_url))
+            .get(&url)
             .bearer_auth(self.api_key.expose_secret())
             .query(&[("team_id", team_id)])
             .send()
             .await
-            .map_err(|e| RelayError::Network(e.to_string()))?;
+            .map_err(|e| {
+                tracing::warn!(
+                    relay_url = %url,
+                    error = %e,
+                    "RelayClient::get_signing_secret: network request failed"
+                );
+                RelayError::Network(e.to_string())
+            })?;
 
         if !resp.status().is_success() {
             let status = resp.status().as_u16();
             let body = resp.text().await.unwrap_or_default();
+            tracing::warn!(
+                relay_url = %url,
+                status = status,
+                body = %body,
+                "RelayClient::get_signing_secret: channel-relay returned error"
+            );
             return Err(RelayError::Api {
                 status,
                 message: body,
             });
         }
+        tracing::debug!(
+            relay_url = %url,
+            "RelayClient::get_signing_secret: received successful response"
+        );
 
         let body: serde_json::Value = resp
             .json()
diff --git a/src/channels/web/server.rs b/src/channels/web/server.rs
index 3c0fc1a9..f46a5367 100644
--- a/src/channels/web/server.rs
+++ b/src/channels/web/server.rs
@@ -861,10 +861,10 @@ async fn oauth_callback_handler(
 
     let result: Result<(), String> = async {
         let token_response = if let Some(proxy_url) = &exchange_proxy_url {
-            let gateway_token = flow.gateway_token.as_deref().unwrap_or_default();
+            let oauth_proxy_auth_token = flow.oauth_proxy_auth_token().unwrap_or_default();
             oauth_defaults::exchange_via_proxy(oauth_defaults::ProxyTokenExchangeRequest {
                 proxy_url,
-                gateway_token,
+                gateway_token: oauth_proxy_auth_token,
                 token_url: &flow.token_url,
                 client_id: &flow.client_id,
                 client_secret: flow.client_secret.as_deref(),
@@ -1202,11 +1202,31 @@ async fn slack_relay_oauth_callback_handler(
 
         // Store team_id in settings
         let team_id_key = format!("relay:{}:team_id", DEFAULT_RELAY_NAME);
-        let _ = store
+        tracing::info!(
+            relay = DEFAULT_RELAY_NAME,
+            owner_id = %state.owner_id,
+            team_id_key = %team_id_key,
+            "relay OAuth callback: storing team_id in settings"
+        );
+        store
             .set_setting(&state.owner_id, &team_id_key, &serde_json::json!(team_id))
-            .await;
+            .await
+            .map_err(|e| {
+                tracing::error!(
+                    relay = DEFAULT_RELAY_NAME,
+                    owner_id = %state.owner_id,
+                    error = %e,
+                    "relay OAuth callback: failed to persist team_id to settings store"
+                );
+                format!("Failed to persist relay team_id: {e}")
+            })?;
 
         // Activate the relay channel
+        tracing::info!(
+            relay = DEFAULT_RELAY_NAME,
+            owner_id = %state.owner_id,
+            "relay OAuth callback: activating relay channel"
+        );
         ext_mgr
             .activate_stored_relay(DEFAULT_RELAY_NAME, &state.owner_id)
             .await
@@ -2206,6 +2226,11 @@ async fn extensions_activate_handler(
     AuthenticatedUser(user): AuthenticatedUser,
     Path(name): Path<String>,
 ) -> Result<Json<ActionResponse>, (StatusCode, String)> {
+    tracing::debug!(
+        extension = %name,
+        user_id = %user.user_id,
+        "extensions_activate_handler: received activate request"
+    );
     let ext_mgr = state.extension_manager.as_ref().ok_or((
         StatusCode::NOT_IMPLEMENTED,
         "Extension manager not available (secrets store required)".to_string(),
@@ -2213,6 +2238,10 @@ async fn extensions_activate_handler(
 
     match ext_mgr.activate(&name, &user.user_id).await {
         Ok(result) => {
+            tracing::info!(
+                extension = %name,
+                "extensions_activate_handler: activation succeeded"
+            );
             // Activation loaded the WASM module. Check if the tool needs
             // OAuth scope expansion (e.g., adding google-docs when gmail
             // already has a token but missing the documents scope).
@@ -2231,6 +2260,13 @@ async fn extensions_activate_handler(
                 crate::extensions::ExtensionError::AuthRequired
             );
 
+            tracing::debug!(
+                extension = %name,
+                error = %activate_err,
+                needs_auth = needs_auth,
+                "extensions_activate_handler: activation failed, attempting auth fallback"
+            );
+
             if !needs_auth {
                 return Ok(Json(ActionResponse::fail(activate_err.to_string())));
             }
@@ -2238,10 +2274,21 @@ async fn extensions_activate_handler(
             // Activation failed due to auth; try authenticating first.
             match ext_mgr.auth(&name, &user.user_id).await {
                 Ok(auth_result) if auth_result.is_authenticated() => {
+                    tracing::debug!(
+                        extension = %name,
+                        "extensions_activate_handler: auth reports authenticated, retrying activate"
+                    );
                     // Auth succeeded, retry activation.
                     match ext_mgr.activate(&name, &user.user_id).await {
                         Ok(result) => Ok(Json(ActionResponse::ok(result.message))),
-                        Err(e) => Ok(Json(ActionResponse::fail(e.to_string()))),
+                        Err(e) => {
+                            tracing::warn!(
+                                extension = %name,
+                                error = %e,
+                                "extensions_activate_handler: retry after auth still failed"
+                            );
+                            Ok(Json(ActionResponse::fail(e.to_string())))
+                        }
                     }
                 }
                 Ok(auth_result) => {
@@ -3420,6 +3467,160 @@ mod tests {
             .with_state(state)
     }
 
+    #[derive(Clone, Debug)]
+    struct RecordedOauthProxyRequest {
+        authorization: Option<String>,
+        form: std::collections::HashMap<String, String>,
+    }
+
+    #[derive(Clone)]
+    struct MockOauthProxyState {
+        requests: Arc<tokio::sync::Mutex<Vec<RecordedOauthProxyRequest>>>,
+    }
+
+    struct MockOauthProxyServer {
+        addr: std::net::SocketAddr,
+        requests: Arc<tokio::sync::Mutex<Vec<RecordedOauthProxyRequest>>>,
+        shutdown_tx: Option<tokio::sync::oneshot::Sender<()>>,
+        server_task: Option<tokio::task::JoinHandle<()>>,
+    }
+
+    impl MockOauthProxyServer {
+        async fn start() -> Self {
+            async fn exchange_handler(
+                State(state): State<MockOauthProxyState>,
+                headers: axum::http::HeaderMap,
+                axum::Form(form): axum::Form<std::collections::HashMap<String, String>>,
+            ) -> Json<serde_json::Value> {
+                state.requests.lock().await.push(RecordedOauthProxyRequest {
+                    authorization: headers
+                        .get(axum::http::header::AUTHORIZATION)
+                        .and_then(|value| value.to_str().ok())
+                        .map(str::to_string),
+                    form,
+                });
+                Json(serde_json::json!({
+                    "access_token": "proxy-access-token",
+                    "refresh_token": "proxy-refresh-token",
+                    "expires_in": 7200
+                }))
+            }
+
+            let requests = Arc::new(tokio::sync::Mutex::new(Vec::new()));
+            let listener = tokio::net::TcpListener::bind("127.0.0.1:0")
+                .await
+                .expect("bind mock oauth proxy");
+            let addr = listener.local_addr().expect("mock oauth proxy addr");
+            let app = Router::new()
+                .route("/oauth/exchange", post(exchange_handler))
+                .with_state(MockOauthProxyState {
+                    requests: Arc::clone(&requests),
+                });
+            let (shutdown_tx, shutdown_rx) = tokio::sync::oneshot::channel::<()>();
+            let server_task = tokio::spawn(async move {
+                let _ = axum::serve(listener, app)
+                    .with_graceful_shutdown(async {
+                        let _ = shutdown_rx.await;
+                    })
+                    .await;
+            });
+
+            Self {
+                addr,
+                requests,
+                shutdown_tx: Some(shutdown_tx),
+                server_task: Some(server_task),
+            }
+        }
+
+        fn base_url(&self) -> String {
+            format!("http://{}", self.addr)
+        }
+
+        async fn requests(&self) -> Vec<RecordedOauthProxyRequest> {
+            self.requests.lock().await.clone()
+        }
+
+        async fn shutdown(mut self) {
+            if let Some(tx) = self.shutdown_tx.take() {
+                let _ = tx.send(());
+            }
+            if let Some(task) = self.server_task.take() {
+                let _ = task.await;
+            }
+        }
+    }
+
+    impl Drop for MockOauthProxyServer {
+        fn drop(&mut self) {
+            if let Some(tx) = self.shutdown_tx.take() {
+                let _ = tx.send(());
+            }
+            if let Some(task) = self.server_task.take() {
+                task.abort();
+            }
+        }
+    }
+
+    struct EnvVarGuard {
+        key: &'static str,
+        original: Option<String>,
+    }
+
+    impl Drop for EnvVarGuard {
+        fn drop(&mut self) {
+            // SAFETY: Tests use lock_env() to serialize environment access.
+            unsafe {
+                if let Some(ref value) = self.original {
+                    std::env::set_var(self.key, value);
+                } else {
+                    std::env::remove_var(self.key);
+                }
+            }
+        }
+    }
+
+    fn set_env_var(key: &'static str, value: Option<&str>) -> EnvVarGuard {
+        let original = std::env::var(key).ok();
+        // SAFETY: Tests use lock_env() to serialize environment access.
+        unsafe {
+            if let Some(value) = value {
+                std::env::set_var(key, value);
+            } else {
+                std::env::remove_var(key);
+            }
+        }
+        EnvVarGuard { key, original }
+    }
+
+    fn fresh_pending_oauth_flow(
+        secrets: Arc<dyn crate::secrets::SecretsStore + Send + Sync>,
+        sse_manager: Option<Arc<SseManager>>,
+        oauth_proxy_auth_token: Option<String>,
+    ) -> crate::cli::oauth_defaults::PendingOAuthFlow {
+        crate::cli::oauth_defaults::PendingOAuthFlow {
+            extension_name: "test_tool".to_string(),
+            display_name: "Test Tool".to_string(),
+            token_url: "https://example.com/token".to_string(),
+            client_id: "client123".to_string(),
+            client_secret: None,
+            redirect_uri: "https://example.com/oauth/callback".to_string(),
+            code_verifier: Some("test-code-verifier".to_string()),
+            access_token_field: "access_token".to_string(),
+            secret_name: "test_token".to_string(),
+            provider: Some("google".to_string()),
+            validation_endpoint: None,
+            scopes: vec!["email".to_string()],
+            user_id: "test".to_string(),
+            secrets,
+            sse_manager,
+            gateway_token: oauth_proxy_auth_token,
+            token_exchange_extra_params: std::collections::HashMap::new(),
+            client_id_secret_name: None,
+            created_at: std::time::Instant::now(),
+        }
+    }
+
     #[tokio::test]
     async fn test_extensions_setup_submit_returns_failure_when_not_activated() {
         use axum::body::Body;
@@ -4077,6 +4278,284 @@ mod tests {
         );
     }
 
+    #[tokio::test]
+    async fn test_oauth_callback_accepts_versioned_hosted_state_without_instance_name() {
+        use axum::body::Body;
+        use tower::ServiceExt;
+
+        let secrets: Arc<dyn crate::secrets::SecretsStore + Send + Sync> =
+            Arc::new(crate::secrets::InMemorySecretsStore::new(Arc::new(
+                crate::secrets::SecretsCrypto::new(secrecy::SecretString::from(
+                    TEST_GATEWAY_CRYPTO_KEY.to_string(),
+                ))
+                .expect("crypto"),
+            )));
+        let (ext_mgr, _wasm_tools_dir, _wasm_channels_dir) = test_ext_mgr(secrets.clone());
+
+        let Some(created_at) = expired_flow_created_at() else {
+            eprintln!(
+                "Skipping versioned OAuth state without instance test: monotonic uptime below expiry window"
+            );
+            return;
+        };
+        let flow = crate::cli::oauth_defaults::PendingOAuthFlow {
+            extension_name: "test_tool".to_string(),
+            display_name: "Test Tool".to_string(),
+            token_url: "https://example.com/token".to_string(),
+            client_id: "client123".to_string(),
+            client_secret: None,
+            redirect_uri: "https://example.com/oauth/callback".to_string(),
+            code_verifier: None,
+            access_token_field: "access_token".to_string(),
+            secret_name: "test_token".to_string(),
+            provider: None,
+            validation_endpoint: None,
+            scopes: vec![],
+            user_id: "test".to_string(),
+            secrets,
+            sse_manager: None,
+            gateway_token: None,
+            token_exchange_extra_params: std::collections::HashMap::new(),
+            client_id_secret_name: None,
+            created_at,
+        };
+
+        ext_mgr
+            .pending_oauth_flows()
+            .write()
+            .await
+            .insert("test_nonce".to_string(), flow);
+
+        let state = test_gateway_state(Some(ext_mgr.clone()));
+        let app = test_oauth_router(state);
+        let versioned_state =
+            crate::cli::oauth_defaults::encode_hosted_oauth_state("test_nonce", None);
+
+        let req = axum::http::Request::builder()
+            .uri(format!(
+                "/oauth/callback?code=fake_code&state={}",
+                urlencoding::encode(&versioned_state)
+            ))
+            .body(Body::empty())
+            .expect("request");
+
+        let resp = ServiceExt::<axum::http::Request<Body>>::oneshot(app, req)
+            .await
+            .expect("response");
+        assert_eq!(resp.status(), StatusCode::OK);
+
+        let body = axum::body::to_bytes(resp.into_body(), 1024 * 64)
+            .await
+            .expect("body");
+        let html = String::from_utf8_lossy(&body);
+        assert!(html.contains("Authorization Failed"));
+        assert!(
+            ext_mgr
+                .pending_oauth_flows()
+                .read()
+                .await
+                .get("test_nonce")
+                .is_none()
+        );
+    }
+
+    #[allow(clippy::await_holding_lock)]
+    #[tokio::test]
+    async fn test_oauth_callback_happy_path_with_gateway_token_fallback() {
+        use axum::body::Body;
+        use tower::ServiceExt;
+
+        let proxy = MockOauthProxyServer::start().await;
+        // Keep the process-wide env locked for the full callback so the handler
+        // sees a stable proxy URL/token configuration throughout the test.
+        let _env_guard = crate::config::helpers::lock_env();
+        let _exchange_url_guard =
+            set_env_var("IRONCLAW_OAUTH_EXCHANGE_URL", Some(&proxy.base_url()));
+        let _proxy_auth_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", None);
+        let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-test-token"));
+
+        let secrets = test_secrets_store();
+        let (ext_mgr, _wasm_tools_dir, _wasm_channels_dir) = test_ext_mgr(Arc::clone(&secrets));
+        let sse_mgr = Arc::new(SseManager::new());
+        let mut receiver = sse_mgr.sender().subscribe();
+        let flow = fresh_pending_oauth_flow(
+            Arc::clone(&secrets),
+            Some(Arc::clone(&sse_mgr)),
+            crate::cli::oauth_defaults::oauth_proxy_auth_token(),
+        );
+
+        ext_mgr
+            .pending_oauth_flows()
+            .write()
+            .await
+            .insert("test_nonce".to_string(), flow);
+
+        let state = test_gateway_state(Some(ext_mgr.clone()));
+        let app = test_oauth_router(state);
+        let versioned_state =
+            crate::cli::oauth_defaults::encode_hosted_oauth_state("test_nonce", Some("myinstance"));
+
+        let req = axum::http::Request::builder()
+            .uri(format!(
+                "/oauth/callback?code=fake_code&state={}",
+                urlencoding::encode(&versioned_state)
+            ))
+            .body(Body::empty())
+            .expect("request");
+
+        let resp = ServiceExt::<axum::http::Request<Body>>::oneshot(app, req)
+            .await
+            .expect("response");
+        assert_eq!(resp.status(), StatusCode::OK);
+
+        let body = axum::body::to_bytes(resp.into_body(), 1024 * 64)
+            .await
+            .expect("body");
+        let html = String::from_utf8_lossy(&body);
+        assert!(html.contains("Test Tool Connected"));
+
+        let requests = proxy.requests().await;
+        assert_eq!(requests.len(), 1);
+        assert_eq!(
+            requests[0].authorization.as_deref(),
+            Some("Bearer gateway-test-token")
+        );
+        assert_eq!(
+            requests[0].form.get("code").map(String::as_str),
+            Some("fake_code")
+        );
+        assert_eq!(
+            requests[0].form.get("code_verifier").map(String::as_str),
+            Some("test-code-verifier")
+        );
+
+        let access_token = secrets
+            .get_decrypted("test", "test_token")
+            .await
+            .expect("access token stored");
+        assert_eq!(access_token.expose(), "proxy-access-token");
+
+        let refresh_token = secrets
+            .get_decrypted("test", "test_token_refresh_token")
+            .await
+            .expect("refresh token stored");
+        assert_eq!(refresh_token.expose(), "proxy-refresh-token");
+
+        match receiver.recv().await.expect("auth_completed event").event {
+            crate::channels::web::types::AppEvent::AuthCompleted {
+                extension_name,
+                success,
+                ..
+            } => {
+                assert_eq!(extension_name, "test_tool");
+                assert!(success, "OAuth callback should broadcast success");
+            }
+            event => panic!("expected AuthCompleted event, got {event:?}"),
+        }
+
+        proxy.shutdown().await;
+    }
+
+    #[allow(clippy::await_holding_lock)]
+    #[tokio::test]
+    async fn test_oauth_callback_happy_path_with_dedicated_proxy_auth_token() {
+        use axum::body::Body;
+        use tower::ServiceExt;
+
+        let proxy = MockOauthProxyServer::start().await;
+        // Keep the process-wide env locked for the full callback so the handler
+        // sees a stable proxy URL/token configuration throughout the test.
+        let _env_guard = crate::config::helpers::lock_env();
+        let _exchange_url_guard =
+            set_env_var("IRONCLAW_OAUTH_EXCHANGE_URL", Some(&proxy.base_url()));
+        let _proxy_auth_guard = set_env_var(
+            "IRONCLAW_OAUTH_PROXY_AUTH_TOKEN",
+            Some("shared-oauth-proxy-secret"),
+        );
+        let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", None);
+
+        let secrets = test_secrets_store();
+        let (ext_mgr, _wasm_tools_dir, _wasm_channels_dir) = test_ext_mgr(Arc::clone(&secrets));
+        let sse_mgr = Arc::new(SseManager::new());
+        let mut receiver = sse_mgr.sender().subscribe();
+        let flow = fresh_pending_oauth_flow(
+            Arc::clone(&secrets),
+            Some(Arc::clone(&sse_mgr)),
+            crate::cli::oauth_defaults::oauth_proxy_auth_token(),
+        );
+
+        ext_mgr
+            .pending_oauth_flows()
+            .write()
+            .await
+            .insert("test_nonce".to_string(), flow);
+
+        let state = test_gateway_state(Some(ext_mgr.clone()));
+        let app = test_oauth_router(state);
+        let versioned_state =
+            crate::cli::oauth_defaults::encode_hosted_oauth_state("test_nonce", None);
+
+        let req = axum::http::Request::builder()
+            .uri(format!(
+                "/oauth/callback?code=fake_code&state={}",
+                urlencoding::encode(&versioned_state)
+            ))
+            .body(Body::empty())
+            .expect("request");
+
+        let resp = ServiceExt::<axum::http::Request<Body>>::oneshot(app, req)
+            .await
+            .expect("response");
+        assert_eq!(resp.status(), StatusCode::OK);
+
+        let body = axum::body::to_bytes(resp.into_body(), 1024 * 64)
+            .await
+            .expect("body");
+        let html = String::from_utf8_lossy(&body);
+        assert!(html.contains("Test Tool Connected"));
+
+        let requests = proxy.requests().await;
+        assert_eq!(requests.len(), 1);
+        assert_eq!(
+            requests[0].authorization.as_deref(),
+            Some("Bearer shared-oauth-proxy-secret")
+        );
+        assert_eq!(
+            requests[0].form.get("code").map(String::as_str),
+            Some("fake_code")
+        );
+        assert_eq!(
+            requests[0].form.get("code_verifier").map(String::as_str),
+            Some("test-code-verifier")
+        );
+
+        let access_token = secrets
+            .get_decrypted("test", "test_token")
+            .await
+            .expect("access token stored");
+        assert_eq!(access_token.expose(), "proxy-access-token");
+
+        let refresh_token = secrets
+            .get_decrypted("test", "test_token_refresh_token")
+            .await
+            .expect("refresh token stored");
+        assert_eq!(refresh_token.expose(), "proxy-refresh-token");
+
+        match receiver.recv().await.expect("auth_completed event").event {
+            crate::channels::web::types::AppEvent::AuthCompleted {
+                extension_name,
+                success,
+                ..
+            } => {
+                assert_eq!(extension_name, "test_tool");
+                assert!(success, "OAuth callback should broadcast success");
+            }
+            event => panic!("expected AuthCompleted event, got {event:?}"),
+        }
+
+        proxy.shutdown().await;
+    }
+
     // --- Slack relay OAuth CSRF tests ---
 
     fn test_relay_oauth_router(state: Arc<GatewayState>) -> Router {
diff --git a/src/cli/oauth_defaults.rs b/src/cli/oauth_defaults.rs
index e9001909..384d5833 100644
--- a/src/cli/oauth_defaults.rs
+++ b/src/cli/oauth_defaults.rs
@@ -473,7 +473,8 @@ pub struct PendingOAuthFlow {
     pub secrets: Arc<dyn SecretsStore + Send + Sync>,
     /// SSE broadcast manager for notifying the web UI.
     pub sse_manager: Option<Arc<crate::channels::web::sse::SseManager>>,
-    /// Gateway auth token for authenticating with the platform token exchange proxy.
+    /// OAuth proxy auth token for authenticating with the hosted token exchange proxy.
+    /// Kept as `gateway_token` for public API compatibility.
     pub gateway_token: Option<String>,
     /// Additional form params for the token exchange request.
     /// Used for provider-specific requirements such as RFC 8707 `resource`.
@@ -496,6 +497,12 @@ impl std::fmt::Debug for PendingOAuthFlow {
     }
 }
 
+impl PendingOAuthFlow {
+    pub fn oauth_proxy_auth_token(&self) -> Option<&str> {
+        self.gateway_token.as_deref()
+    }
+}
+
 /// Thread-safe registry of pending OAuth flows, keyed by CSRF `state` parameter.
 pub type PendingOAuthRegistry = Arc<RwLock<HashMap<String, PendingOAuthFlow>>>;
 
@@ -529,6 +536,22 @@ pub fn exchange_proxy_url() -> Option<String> {
         .filter(|url| !url.is_empty())
 }
 
+/// Returns the configured OAuth proxy auth token, if any.
+///
+/// New hosted infra can inject a dedicated shared proxy secret via
+/// `IRONCLAW_OAUTH_PROXY_AUTH_TOKEN`. Existing hosted instances continue to
+/// work by falling back to `GATEWAY_AUTH_TOKEN`.
+pub fn oauth_proxy_auth_token() -> Option<String> {
+    fn normalized_env_value(key: &str) -> Option<String> {
+        crate::config::helpers::env_or_override(key)
+            .map(|value| value.trim().to_string())
+            .filter(|value| !value.is_empty())
+    }
+
+    normalized_env_value("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN")
+        .or_else(|| normalized_env_value("GATEWAY_AUTH_TOKEN"))
+}
+
 /// Maximum age for pending OAuth flows (5 minutes, matching TCP listener timeout).
 pub const OAUTH_FLOW_EXPIRY: Duration = Duration::from_secs(300);
 
@@ -674,6 +697,8 @@ pub fn strip_instance_prefix(state: &str) -> &str {
 
 pub struct ProxyTokenExchangeRequest<'a> {
     pub proxy_url: &'a str,
+    /// OAuth proxy auth token.
+    /// Kept as `gateway_token` for public API compatibility.
     pub gateway_token: &'a str,
     pub token_url: &'a str,
     pub client_id: &'a str,
@@ -687,6 +712,8 @@ pub struct ProxyTokenExchangeRequest<'a> {
 
 pub struct ProxyRefreshTokenRequest<'a> {
     pub proxy_url: &'a str,
+    /// OAuth proxy auth token.
+    /// Kept as `gateway_token` for public API compatibility.
     pub gateway_token: &'a str,
     pub token_url: &'a str,
     pub client_id: &'a str,
@@ -729,7 +756,7 @@ fn oauth_token_response_from_json(
 
 /// Exchange an OAuth authorization code via the platform's token exchange proxy.
 ///
-/// Authenticated via the gateway auth token (Bearer header). The caller may
+/// Authenticated via an OAuth proxy auth token (Bearer header). The caller may
 /// either rely on proxy-side secret lookup or forward a `client_secret` when
 /// the provider requires it.
 ///
@@ -741,7 +768,7 @@ pub async fn exchange_via_proxy(
 ) -> Result<OAuthTokenResponse, OAuthCallbackError> {
     if request.gateway_token.is_empty() {
         return Err(OAuthCallbackError::Io(
-            "Gateway auth token is required for proxy token exchange".to_string(),
+            "OAuth proxy auth token is required for proxy token exchange".to_string(),
         ));
     }
     let exchange_url = format!("{}/oauth/exchange", request.proxy_url.trim_end_matches('/'));
@@ -796,7 +823,7 @@ pub async fn exchange_via_proxy(
 
 /// Refresh an OAuth access token via the platform's token refresh proxy.
 ///
-/// Authenticated via the gateway auth token (Bearer header). The caller may
+/// Authenticated via an OAuth proxy auth token (Bearer header). The caller may
 /// either rely on proxy-side secret lookup or forward a `client_secret` when
 /// the provider requires it.
 pub async fn refresh_token_via_proxy(
@@ -804,7 +831,7 @@ pub async fn refresh_token_via_proxy(
 ) -> Result<OAuthTokenResponse, OAuthCallbackError> {
     if request.gateway_token.is_empty() {
         return Err(OAuthCallbackError::Io(
-            "Gateway auth token is required for proxy token refresh".to_string(),
+            "OAuth proxy auth token is required for proxy token refresh".to_string(),
         ));
     }
 
@@ -1010,6 +1037,37 @@ mod tests {
         }
     }
 
+    struct EnvVarGuard {
+        key: &'static str,
+        original: Option<String>,
+    }
+
+    impl Drop for EnvVarGuard {
+        fn drop(&mut self) {
+            // SAFETY: Under ENV_MUTEX, no concurrent env access.
+            unsafe {
+                if let Some(ref value) = self.original {
+                    std::env::set_var(self.key, value);
+                } else {
+                    std::env::remove_var(self.key);
+                }
+            }
+        }
+    }
+
+    fn set_env_var(key: &'static str, value: Option<&str>) -> EnvVarGuard {
+        let original = std::env::var(key).ok();
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe {
+            if let Some(value) = value {
+                std::env::set_var(key, value);
+            } else {
+                std::env::remove_var(key);
+            }
+        }
+        EnvVarGuard { key, original }
+    }
+
     #[test]
     fn test_hosted_proxy_client_secret_suppresses_builtin_secret() {
         let builtin = builtin_credentials("google_oauth_token").expect("google builtin creds");
@@ -1030,6 +1088,79 @@ mod tests {
         assert_eq!(result, client_secret);
     }
 
+    #[tokio::test]
+    async fn test_exchange_via_proxy_sends_auth_and_form() {
+        let server = MockProxyServer::start().await;
+        let mut extra_token_params = HashMap::new();
+        extra_token_params.insert("resource".to_string(), "https://mcp.notion.com".to_string());
+
+        let response = super::exchange_via_proxy(super::ProxyTokenExchangeRequest {
+            proxy_url: &server.base_url(),
+            gateway_token: "shared-oauth-proxy-secret",
+            code: "auth-code-123",
+            redirect_uri: "https://oauth.example.com/oauth/callback",
+            token_url: "https://oauth2.googleapis.com/token",
+            client_id: TEST_OAUTH_CLIENT_ID,
+            client_secret: Some(TEST_OAUTH_CLIENT_SECRET),
+            access_token_field: "access_token",
+            code_verifier: Some("code-verifier-123"),
+            extra_token_params: &extra_token_params,
+        })
+        .await
+        .expect("proxy exchange succeeds");
+
+        assert_eq!(response.access_token, "proxy-access-token");
+        assert_eq!(
+            response.refresh_token.as_deref(),
+            Some("proxy-refresh-token")
+        );
+        assert_eq!(response.expires_in, Some(7200));
+
+        let requests = server.requests().await;
+        assert_eq!(requests.len(), 1);
+        assert_eq!(
+            requests[0].authorization.as_deref(),
+            Some("Bearer shared-oauth-proxy-secret")
+        );
+        assert_eq!(
+            requests[0].form.get("code").map(String::as_str),
+            Some("auth-code-123")
+        );
+        assert_eq!(
+            requests[0].form.get("redirect_uri").map(String::as_str),
+            Some("https://oauth.example.com/oauth/callback")
+        );
+        assert_eq!(
+            requests[0].form.get("token_url").map(String::as_str),
+            Some("https://oauth2.googleapis.com/token")
+        );
+        assert_eq!(
+            requests[0].form.get("client_id").map(String::as_str),
+            Some(TEST_OAUTH_CLIENT_ID)
+        );
+        assert_eq!(
+            requests[0].form.get("client_secret").map(String::as_str),
+            Some(TEST_OAUTH_CLIENT_SECRET)
+        );
+        assert_eq!(
+            requests[0]
+                .form
+                .get("access_token_field")
+                .map(String::as_str),
+            Some("access_token")
+        );
+        assert_eq!(
+            requests[0].form.get("code_verifier").map(String::as_str),
+            Some("code-verifier-123")
+        );
+        assert_eq!(
+            requests[0].form.get("resource").map(String::as_str),
+            Some("https://mcp.notion.com")
+        );
+
+        server.shutdown().await;
+    }
+
     #[tokio::test]
     async fn test_refresh_token_via_proxy_sends_auth_and_form() {
         let server = MockProxyServer::start().await;
@@ -1535,6 +1666,54 @@ mod tests {
         }
     }
 
+    #[test]
+    fn test_oauth_proxy_auth_token_prefers_dedicated_env() {
+        let _guard = lock_env();
+        let _proxy_guard = set_env_var(
+            "IRONCLAW_OAUTH_PROXY_AUTH_TOKEN",
+            Some("shared-proxy-secret"),
+        );
+        let _gateway_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-token"));
+
+        assert_eq!(
+            crate::cli::oauth_defaults::oauth_proxy_auth_token().as_deref(),
+            Some("shared-proxy-secret")
+        );
+    }
+
+    #[test]
+    fn test_oauth_proxy_auth_token_falls_back_to_gateway_token() {
+        let _guard = lock_env();
+        let _proxy_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", None);
+        let _gateway_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-token"));
+
+        assert_eq!(
+            crate::cli::oauth_defaults::oauth_proxy_auth_token().as_deref(),
+            Some("gateway-token")
+        );
+    }
+
+    #[test]
+    fn test_oauth_proxy_auth_token_whitespace_dedicated_env_falls_back_to_gateway_token() {
+        let _guard = lock_env();
+        let _proxy_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", Some("   "));
+        let _gateway_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-token"));
+
+        assert_eq!(
+            crate::cli::oauth_defaults::oauth_proxy_auth_token().as_deref(),
+            Some("gateway-token")
+        );
+    }
+
+    #[test]
+    fn test_oauth_proxy_auth_token_returns_none_when_unset() {
+        let _guard = lock_env();
+        let _proxy_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", None);
+        let _gateway_guard = set_env_var("GATEWAY_AUTH_TOKEN", None);
+
+        assert_eq!(crate::cli::oauth_defaults::oauth_proxy_auth_token(), None);
+    }
+
     #[test]
     fn test_strip_instance_prefix_with_colon() {
         use crate::cli::oauth_defaults::strip_instance_prefix;
diff --git a/src/context/state.rs b/src/context/state.rs
index f5307947..0bb1f29a 100644
--- a/src/context/state.rs
+++ b/src/context/state.rs
@@ -192,6 +192,9 @@ pub struct JobContext {
     /// but subsequent tools (e.g., `json`) may need the full output. This
     /// stash stores the complete, unsanitized output so tools can reference
     /// previous results by ID via `$tool_call_id` parameter syntax.
+    ///
+    /// Also used for cross-tool implicit state (keys prefixed with `__`) such
+    /// as `__routine_last_name` for fallback recovery in routine tool chains.
     #[serde(skip)]
     pub tool_output_stash: Arc<tokio::sync::RwLock<HashMap<String, String>>>,
     /// User's preferred timezone (IANA name, e.g. "America/New_York"). Defaults to "UTC".
diff --git a/src/extensions/manager.rs b/src/extensions/manager.rs
index 90920767..55b1e96d 100644
--- a/src/extensions/manager.rs
+++ b/src/extensions/manager.rs
@@ -403,9 +403,10 @@ pub struct ExtensionManager {
     /// when running in gateway mode, consumed by the web gateway's
     /// `/oauth/callback` handler.
     pending_oauth_flows: crate::cli::oauth_defaults::PendingOAuthRegistry,
-    /// Gateway auth token for authenticating with the platform token exchange proxy.
-    /// Read once at construction from `GATEWAY_AUTH_TOKEN` env var.
-    gateway_token: Option<String>,
+    /// OAuth proxy auth token for authenticating with the hosted token exchange proxy.
+    /// Resolved once at construction from `IRONCLAW_OAUTH_PROXY_AUTH_TOKEN`,
+    /// then `GATEWAY_AUTH_TOKEN` as a backward-compatible fallback.
+    oauth_proxy_auth_token: Option<String>,
     /// Relay config captured at startup. Used by `auth_channel_relay` and
     /// `activate_channel_relay` instead of re-reading env vars.
     relay_config: Option<crate::config::RelayConfig>,
@@ -535,7 +536,7 @@ impl ExtensionManager {
             activation_errors: RwLock::new(HashMap::new()),
             sse_manager: RwLock::new(None),
             pending_oauth_flows: crate::cli::oauth_defaults::new_pending_oauth_registry(),
-            gateway_token: std::env::var("GATEWAY_AUTH_TOKEN").ok(),
+            oauth_proxy_auth_token: crate::cli::oauth_defaults::oauth_proxy_auth_token(),
             relay_config: crate::config::RelayConfig::from_env(),
             relay_event_tx: Arc::new(tokio::sync::Mutex::new(None)),
             relay_signing_secret_cache: Arc::new(std::sync::Mutex::new(None)),
@@ -659,6 +660,66 @@ impl ExtensionManager {
         })
     }
 
+    /// Resolve the relay URL override for an extension from settings.
+    ///
+    /// Returns `Some(url)` if a non-empty per-extension `relay_url` override is
+    /// set for the given extension; otherwise returns `None` and callers should
+    /// fall back to the env-level `RelayConfig`.
+    ///
+    /// Uses `self.user_id` (owner scope) for consistency with `configure()`,
+    /// which also writes setting_path fields under the owner scope.
+    ///
+    /// The override is validated: only `http` / `https` schemes are accepted
+    /// and the URL must not contain userinfo (embedded credentials).  This
+    /// prevents a malicious override from exfiltrating the instance-wide relay
+    /// API key to an attacker-controlled host.
+    async fn effective_relay_url(&self, name: &str) -> Option<String> {
+        if let Some(ref store) = self.store {
+            let key = format!("extensions.{name}.relay_url");
+            if let Ok(Some(v)) = store.get_setting(&self.user_id, &key).await {
+                let url = v
+                    .as_str()
+                    .map(|s| s.trim().to_string())
+                    .filter(|s| !s.is_empty());
+                if let Some(ref u) = url {
+                    // Validate the override to prevent API-key exfiltration:
+                    // only allow http(s) with no embedded credentials.
+                    match url::Url::parse(u) {
+                        Ok(parsed)
+                            if (parsed.scheme() == "http" || parsed.scheme() == "https")
+                                && parsed.username().is_empty()
+                                && parsed.password().is_none() =>
+                        {
+                            tracing::debug!(
+                                extension = %name,
+                                relay_url_host = %parsed.host_str().unwrap_or("unknown"),
+                                "effective_relay_url: using per-extension override from settings"
+                            );
+                            return url;
+                        }
+                        Ok(parsed) => {
+                            tracing::warn!(
+                                extension = %name,
+                                scheme = %parsed.scheme(),
+                                has_userinfo = !parsed.username().is_empty() || parsed.password().is_some(),
+                                "effective_relay_url: rejecting override — \
+                                 only http/https without embedded credentials is allowed"
+                            );
+                        }
+                        Err(e) => {
+                            tracing::warn!(
+                                extension = %name,
+                                error = %e,
+                                "effective_relay_url: rejecting override — invalid URL"
+                            );
+                        }
+                    }
+                }
+            }
+        }
+        None
+    }
+
     /// Get the shared relay event sender for the webhook endpoint.
     pub fn relay_event_tx(
         &self,
@@ -892,6 +953,46 @@ impl ExtensionManager {
         false
     }
 
+    /// Check whether a stored `team_id` setting exists for the given relay extension.
+    ///
+    /// Unlike [`is_relay_channel`], this does **not** consult the in-memory
+    /// `installed_relay_extensions` set — it only looks at the persistent settings
+    /// store.  This distinction matters for `auth_channel_relay`: an extension can
+    /// be *installed* (present in the in-memory set) but not yet *authenticated*
+    /// (no OAuth completed, no team_id stored).
+    async fn has_stored_team_id(&self, name: &str, _user_id: &str) -> bool {
+        if let Some(ref store) = self.store {
+            let key = format!("relay:{}:team_id", name);
+            // Use owner scope (self.user_id) for consistency: the OAuth callback
+            // stores team_id under state.owner_id which maps to self.user_id.
+            match store.get_setting(&self.user_id, &key).await {
+                Ok(Some(v)) => {
+                    let has_id = v.as_str().is_some_and(|s| !s.is_empty());
+                    tracing::debug!(
+                        extension = %name,
+                        has_team_id = has_id,
+                        "has_stored_team_id: checked store"
+                    );
+                    return has_id;
+                }
+                Ok(None) => {
+                    tracing::debug!(
+                        extension = %name,
+                        "has_stored_team_id: no team_id setting found"
+                    );
+                }
+                Err(e) => {
+                    tracing::warn!(
+                        extension = %name,
+                        error = %e,
+                        "has_stored_team_id: failed to read from settings store"
+                    );
+                }
+            }
+        }
+        false
+    }
+
     /// Restore persisted relay channels after startup.
     ///
     /// Loads the persisted active channel list, filters to relay types (those with
@@ -1418,7 +1519,7 @@ impl ExtensionManager {
             let errors = self.activation_errors.read().await;
             for name in installed.iter() {
                 let active = active_names.contains(name);
-                let authenticated = self.is_relay_channel(name, user_id).await;
+                let authenticated = self.has_stored_team_id(name, user_id).await;
                 let activation_error = errors.get(name).cloned();
                 let registry_entry = self
                     .registry
@@ -2688,7 +2789,7 @@ impl ExtensionManager {
                 user_id: user_id.to_string(),
                 secrets: Arc::clone(&self.secrets),
                 sse_manager: self.sse_manager.read().await.clone(),
-                gateway_token: self.gateway_token.clone(),
+                gateway_token: self.oauth_proxy_auth_token.clone(),
                 token_exchange_extra_params,
                 client_id_secret_name: if server.oauth.is_none() {
                     Some(server.client_id_secret_name())
@@ -3205,7 +3306,7 @@ impl ExtensionManager {
                 user_id: user_id.to_string(),
                 secrets: Arc::clone(&self.secrets),
                 sse_manager: self.sse_manager.read().await.clone(),
-                gateway_token: self.gateway_token.clone(),
+                gateway_token: self.oauth_proxy_auth_token.clone(),
                 token_exchange_extra_params: std::collections::HashMap::new(),
                 client_id_secret_name: None,
                 created_at: std::time::Instant::now(),
@@ -4191,20 +4292,69 @@ impl ExtensionManager {
         name: &str,
         user_id: &str,
     ) -> Result<AuthResult, ExtensionError> {
-        // Check if already authenticated (team_id setting exists)
-        if self.is_relay_channel(name, user_id).await {
+        tracing::debug!(
+            extension = %name,
+            user_id = %user_id,
+            "auth_channel_relay: starting"
+        );
+
+        // Check if already authenticated by looking for a stored team_id.
+        // We intentionally skip the `installed_relay_extensions` in-memory set
+        // here because that set only tracks *installed* extensions — an extension
+        // can be installed (via registry) but not yet authenticated (no OAuth
+        // completed). Checking just `is_relay_channel()` would short-circuit
+        // to "authenticated" even when no team_id exists, preventing the OAuth
+        // flow from being offered to the user.
+        if self.has_stored_team_id(name, user_id).await {
+            tracing::debug!(
+                extension = %name,
+                "auth_channel_relay: already authenticated (team_id in store)"
+            );
             return Ok(AuthResult::authenticated(name, ExtensionKind::ChannelRelay));
         }
 
+        tracing::debug!(
+            extension = %name,
+            "auth_channel_relay: no stored team_id, initiating OAuth"
+        );
+
         // Use relay config captured at startup
-        let relay_config = self.relay_config()?;
+        let relay_config = self.relay_config().map_err(|e| {
+            tracing::warn!(
+                extension = %name,
+                error = %e,
+                "auth_channel_relay: relay config not available — \
+                 CHANNEL_RELAY_URL and CHANNEL_RELAY_API_KEY must be set"
+            );
+            e
+        })?;
+
+        // Allow per-extension URL override from settings
+        let effective_url = self
+            .effective_relay_url(name)
+            .await
+            .unwrap_or_else(|| relay_config.url.clone());
+
+        tracing::debug!(
+            extension = %name,
+            relay_url = %effective_url,
+            "auth_channel_relay: creating relay client for OAuth"
+        );
 
         let client = crate::channels::relay::RelayClient::new(
-            relay_config.url.clone(),
+            effective_url.clone(),
             relay_config.api_key.clone(),
             relay_config.request_timeout_secs,
         )
-        .map_err(|e| ExtensionError::Config(e.to_string()))?;
+        .map_err(|e| {
+            tracing::warn!(
+                extension = %name,
+                relay_url = %effective_url,
+                error = %e,
+                "auth_channel_relay: failed to create relay HTTP client"
+            );
+            ExtensionError::Config(e.to_string())
+        })?;
 
         // Generate CSRF nonce — IronClaw validates this on the callback to ensure
         // the OAuth completion is legitimate. Channel-relay embeds it in the signed
@@ -4216,18 +4366,44 @@ impl ExtensionManager {
         self.secrets
             .create(user_id, CreateSecretParams::new(&state_key, &state_nonce))
             .await
-            .map_err(|e| ExtensionError::AuthFailed(format!("Failed to store OAuth state: {e}")))?;
+            .map_err(|e| {
+                tracing::warn!(
+                    extension = %name,
+                    error = %e,
+                    "auth_channel_relay: failed to store OAuth state nonce"
+                );
+                ExtensionError::AuthFailed(format!("Failed to store OAuth state: {e}"))
+            })?;
 
         // Channel-relay derives all URLs from trusted instance_url in chat-api.
         // We only pass the nonce for CSRF validation on the callback.
+        tracing::debug!(
+            extension = %name,
+            relay_url = %effective_url,
+            "auth_channel_relay: calling initiate_oauth on channel-relay"
+        );
         match client.initiate_oauth(Some(&state_nonce)).await {
-            Ok(auth_url) => Ok(AuthResult::awaiting_authorization(
-                name,
-                ExtensionKind::ChannelRelay,
-                auth_url,
-                "redirect".to_string(),
-            )),
-            Err(e) => Err(ExtensionError::AuthFailed(e.to_string())),
+            Ok(auth_url) => {
+                tracing::info!(
+                    extension = %name,
+                    "auth_channel_relay: OAuth URL obtained, awaiting user authorization"
+                );
+                Ok(AuthResult::awaiting_authorization(
+                    name,
+                    ExtensionKind::ChannelRelay,
+                    auth_url,
+                    "redirect".to_string(),
+                ))
+            }
+            Err(e) => {
+                tracing::warn!(
+                    extension = %name,
+                    relay_url = %effective_url,
+                    error = %e,
+                    "auth_channel_relay: initiate_oauth call to channel-relay failed"
+                );
+                Err(ExtensionError::AuthFailed(e.to_string()))
+            }
         }
     }
 
@@ -4237,40 +4413,112 @@ impl ExtensionManager {
         name: &str,
         user_id: &str,
     ) -> Result<ActivateResult, ExtensionError> {
+        tracing::debug!(
+            extension = %name,
+            user_id = %user_id,
+            "activate_channel_relay: starting"
+        );
+
         let team_id_key = format!("relay:{}:team_id", name);
 
         // Get team_id from settings (stored by the OAuth callback)
         let team_id = if let Some(ref store) = self.store {
-            store
-                .get_setting(user_id, &team_id_key)
-                .await
-                .ok()
-                .flatten()
-                .and_then(|v| v.as_str().map(|s| s.to_string()))
-                .unwrap_or_default()
+            match store.get_setting(user_id, &team_id_key).await {
+                Ok(Some(v)) => {
+                    let id = v.as_str().map(|s| s.to_string()).unwrap_or_default();
+                    tracing::debug!(
+                        extension = %name,
+                        team_id_empty = id.is_empty(),
+                        "activate_channel_relay: loaded team_id from store"
+                    );
+                    id
+                }
+                Ok(None) => {
+                    tracing::debug!(
+                        extension = %name,
+                        setting_key = %team_id_key,
+                        "activate_channel_relay: no team_id in settings store"
+                    );
+                    String::new()
+                }
+                Err(e) => {
+                    tracing::warn!(
+                        extension = %name,
+                        error = %e,
+                        "activate_channel_relay: failed to read team_id from settings store"
+                    );
+                    String::new()
+                }
+            }
         } else {
+            tracing::debug!(
+                extension = %name,
+                "activate_channel_relay: no settings store available"
+            );
             String::new()
         };
 
         if team_id.is_empty() {
+            tracing::debug!(
+                extension = %name,
+                "activate_channel_relay: team_id is empty, returning AuthRequired"
+            );
             return Err(ExtensionError::AuthRequired);
         }
 
         // Use relay config captured at startup
-        let relay_config = self.relay_config()?;
+        let relay_config = self.relay_config().map_err(|e| {
+            tracing::warn!(
+                extension = %name,
+                error = %e,
+                "activate_channel_relay: relay config not available"
+            );
+            e
+        })?;
+
+        // Allow per-extension URL override from settings
+        let effective_url = self
+            .effective_relay_url(name)
+            .await
+            .unwrap_or_else(|| relay_config.url.clone());
+
+        tracing::debug!(
+            extension = %name,
+            relay_url = %effective_url,
+            "activate_channel_relay: relay config loaded"
+        );
 
         let instance_id = self.relay_instance_id(relay_config, user_id);
 
         let client = crate::channels::relay::RelayClient::new(
-            relay_config.url.clone(),
+            effective_url.clone(),
             relay_config.api_key.clone(),
             relay_config.request_timeout_secs,
         )
-        .map_err(|e| ExtensionError::ActivationFailed(e.to_string()))?;
+        .map_err(|e| {
+            tracing::warn!(
+                extension = %name,
+                relay_url = %effective_url,
+                error = %e,
+                "activate_channel_relay: failed to create relay HTTP client"
+            );
+            ExtensionError::ActivationFailed(e.to_string())
+        })?;
 
         // Fetch the per-instance signing secret from channel-relay.
         // This must succeed — there is no fallback.
+        tracing::debug!(
+            extension = %name,
+            relay_url = %effective_url,
+            "activate_channel_relay: fetching signing secret from channel-relay"
+        );
         let signing_secret = client.get_signing_secret(&team_id).await.map_err(|e| {
+            tracing::warn!(
+                extension = %name,
+                relay_url = %effective_url,
+                error = %e,
+                "activate_channel_relay: failed to fetch signing secret from channel-relay"
+            );
             ExtensionError::Config(format!("Failed to fetch relay signing secret: {e}"))
         })?;
 
@@ -4289,16 +4537,29 @@ impl ExtensionManager {
         // Hot-add to channel manager
         let cm_guard = self.relay_channel_manager.read().await;
         let channel_mgr = cm_guard.as_ref().ok_or_else(|| {
+            tracing::warn!(
+                extension = %name,
+                "activate_channel_relay: channel manager not initialized"
+            );
             ExtensionError::ActivationFailed("Channel manager not initialized".to_string())
         })?;
 
-        channel_mgr
-            .hot_add(Box::new(channel))
-            .await
-            .map_err(|e| ExtensionError::ActivationFailed(e.to_string()))?;
+        channel_mgr.hot_add(Box::new(channel)).await.map_err(|e| {
+            tracing::warn!(
+                extension = %name,
+                error = %e,
+                "activate_channel_relay: hot_add to channel manager failed"
+            );
+            ExtensionError::ActivationFailed(e.to_string())
+        })?;
 
         if let Ok(mut cache) = self.relay_signing_secret_cache.lock() {
             *cache = Some(signing_secret);
+        } else {
+            tracing::warn!(
+                extension = %name,
+                "activate_channel_relay: failed to cache signing secret (mutex poisoned)"
+            );
         }
 
         // Store the event sender so the web gateway's relay webhook endpoint can push events
@@ -4316,6 +4577,12 @@ impl ExtensionManager {
         self.broadcast_extension_status(name, "active", Some(&status_msg))
             .await;
 
+        tracing::info!(
+            extension = %name,
+            instance_id = %instance_id,
+            "activate_channel_relay: relay channel activated successfully"
+        );
+
         Ok(ActivateResult {
             name: name.to_string(),
             kind: ExtensionKind::ChannelRelay,
@@ -4595,6 +4862,41 @@ impl ExtensionManager {
                 }
                 Ok(ExtensionSetupSchema { secrets, fields })
             }
+            ExtensionKind::ChannelRelay => {
+                let relay_url_key = format!("extensions.{name}.relay_url");
+                let current_url = if let Some(ref store) = self.store {
+                    match store.get_setting(&self.user_id, &relay_url_key).await {
+                        Ok(value_opt) => value_opt
+                            .and_then(|v| v.as_str().map(|s| s.to_string()))
+                            .filter(|s| !s.is_empty()),
+                        Err(e) => {
+                            tracing::warn!(
+                                extension = %name,
+                                setting_key = %relay_url_key,
+                                error = %e,
+                                "get_setup_schema: failed to read relay_url from settings"
+                            );
+                            None
+                        }
+                    }
+                } else {
+                    None
+                };
+                let env_url = self.relay_config.as_ref().map(|c| c.url.as_str());
+                Ok(ExtensionSetupSchema {
+                    secrets: Vec::new(),
+                    fields: vec![crate::channels::web::types::SetupFieldInfo {
+                        name: "relay_url".to_string(),
+                        prompt: format!(
+                            "Channel-relay service URL (leave empty to use env default{})",
+                            env_url.map(|u| format!(": {u}")).unwrap_or_default()
+                        ),
+                        optional: true,
+                        provided: current_url.is_some(),
+                        input_type: crate::tools::wasm::ToolSetupFieldInputType::Text,
+                    }],
+                })
+            }
             _ => Ok(ExtensionSetupSchema {
                 secrets: Vec::new(),
                 fields: Vec::new(),
@@ -4997,7 +5299,17 @@ impl ExtensionManager {
                 names.insert(server.token_secret_name());
                 (names, Vec::new())
             }
-            ExtensionKind::ChannelRelay => (std::collections::HashSet::new(), Vec::new()),
+            ExtensionKind::ChannelRelay => {
+                let relay_fields = vec![crate::tools::wasm::ToolFieldSetupSchema {
+                    name: "relay_url".to_string(),
+                    prompt: "Channel-relay service URL override".to_string(),
+                    optional: true,
+                    setting_path: Some(format!("extensions.{name}.relay_url")),
+                    input_type: crate::tools::wasm::ToolSetupFieldInputType::Text,
+                    restart_required: false,
+                }];
+                (std::collections::HashSet::new(), relay_fields)
+            }
         };
 
         let allowed_fields: std::collections::HashSet<String> =
@@ -5088,13 +5400,28 @@ impl ExtensionManager {
                 )));
             }
             let trimmed = field_value.trim();
+            let field_def = setup_field_defs.get(field_name);
+
+            // Empty value on an optional field with a setting_path: clear the
+            // stored override so the system reverts to the env/default value.
             if trimmed.is_empty() {
+                if let Some(def) = field_def
+                    && def.optional
+                {
+                    stored_fields.remove(field_name);
+                    if let Some(setting_path) = &def.setting_path {
+                        Self::validate_setup_setting_path(name, setting_path)?;
+                        if let Some(store) = self.store.as_ref() {
+                            let _ = store.delete_setting(&self.user_id, setting_path).await;
+                        }
+                    }
+                }
                 continue;
             }
 
             stored_fields.insert(field_name.clone(), trimmed.to_string());
 
-            if let Some(field_def) = setup_field_defs.get(field_name) {
+            if let Some(field_def) = field_def {
                 if field_def.restart_required {
                     restart_required = true;
                 }
@@ -7058,6 +7385,39 @@ mod tests {
         );
     }
 
+    /// Regression: installed-but-not-authenticated relay must NOT short-circuit
+    /// `auth_channel_relay()` to "authenticated".  Previously, `auth_channel_relay`
+    /// called `is_relay_channel()` which checked the in-memory
+    /// `installed_relay_extensions` set; that returned `true` even when no team_id
+    /// existed in the store, so the OAuth URL was never offered.
+    #[tokio::test]
+    async fn test_auth_channel_relay_installed_without_team_id_is_not_authenticated() {
+        let dir = tempfile::tempdir().expect("temp dir");
+        let mgr = make_test_manager(None, dir.path().to_path_buf());
+
+        // Mark as installed (simulates clicking Install in the UI)
+        mgr.installed_relay_extensions
+            .write()
+            .await
+            .insert("slack-relay".to_string());
+
+        // Without a stored team_id, auth should NOT return authenticated.
+        // It should fail because relay config is missing (no CHANNEL_RELAY_URL),
+        // but the key assertion is that it does NOT return Ok(authenticated).
+        let result = mgr.auth_channel_relay("slack-relay", "test").await;
+        match result {
+            Ok(ref auth_result) if auth_result.is_authenticated() => {
+                panic!(
+                    "auth_channel_relay returned authenticated for installed-but-no-team-id relay; \
+                     expected either an OAuth URL or a config error"
+                );
+            }
+            _ => {
+                // Config error (no relay URL) or awaiting_authorization — both are correct
+            }
+        }
+    }
+
     #[tokio::test]
     async fn test_remove_relay_shuts_down_via_relay_channel_manager() {
         // Regression: remove() only checked channel_runtime for shutdown, missing
diff --git a/src/tools/builtin/routine.rs b/src/tools/builtin/routine.rs
index bbc24139..76f6e38b 100644
--- a/src/tools/builtin/routine.rs
+++ b/src/tools/builtin/routine.rs
@@ -650,6 +650,23 @@ pub(crate) fn routine_update_parameters_schema() -> Value {
     })
 }
 
+const ROUTINE_LAST_NAME_STASH_KEY: &str = "__routine_last_name";
+
+async fn stash_last_routine_name(ctx: &JobContext, name: &str) {
+    ctx.tool_output_stash
+        .write()
+        .await
+        .insert(ROUTINE_LAST_NAME_STASH_KEY.to_string(), name.to_string());
+}
+
+async fn restore_last_routine_name(ctx: &JobContext) -> Option<String> {
+    ctx.tool_output_stash
+        .read()
+        .await
+        .get(ROUTINE_LAST_NAME_STASH_KEY)
+        .cloned()
+}
+
 fn nested_object<'a>(params: &'a Value, field: &str) -> Option<&'a Map<String, Value>> {
     params.get(field).and_then(Value::as_object)
 }
@@ -1093,6 +1110,7 @@ impl Tool for RoutineCreateTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
         let normalized = parse_routine_create_request(&params)?;
+        stash_last_routine_name(ctx, &normalized.name).await;
         let trigger = build_routine_trigger(&normalized.trigger);
         let action =
             build_routine_action(&normalized.name, &normalized.prompt, &normalized.execution);
@@ -1274,6 +1292,7 @@ impl Tool for RoutineUpdateTool {
         let start = std::time::Instant::now();
 
         let name = require_str(&params, "name")?;
+        stash_last_routine_name(ctx, name).await;
 
         let mut routine = self
             .store
@@ -1411,11 +1430,24 @@ impl Tool for RoutineDeleteTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let name = require_str(&params, "name")?;
+        let name = if let Some(name) = params.get("name").and_then(|v| v.as_str()) {
+            if name.trim().is_empty() {
+                return Err(ToolError::InvalidParameters(
+                    "'name' parameter cannot be empty".to_string(),
+                ));
+            }
+            name.to_string()
+        } else {
+            restore_last_routine_name(ctx).await.ok_or_else(|| {
+                ToolError::InvalidParameters(
+                    "missing 'name' parameter and no previous routine target to infer".to_string(),
+                )
+            })?
+        };
 
         let routine = self
             .store
-            .get_routine_by_name(&ctx.user_id, name)
+            .get_routine_by_name(&ctx.user_id, &name)
             .await
             .map_err(|e| ToolError::ExecutionFailed(format!("DB error: {e}")))?
             .ok_or_else(|| ToolError::ExecutionFailed(format!("routine '{}' not found", name)))?;
@@ -1430,7 +1462,7 @@ impl Tool for RoutineDeleteTool {
         self.engine.refresh_event_cache().await;
 
         let result = serde_json::json!({
-            "name": name,
+            "name": &name,
             "deleted": deleted,
         });
 
diff --git a/src/tools/mcp/client.rs b/src/tools/mcp/client.rs
index 148f5a86..32c5767d 100644
--- a/src/tools/mcp/client.rs
+++ b/src/tools/mcp/client.rs
@@ -117,6 +117,11 @@ impl McpClient {
     /// The config must use HTTP transport (the default); for stdio/UDS use `new_with_transport`.
     ///
     /// Returns an error if the config uses a non-HTTP transport.
+    ///
+    /// **Note:** The session manager is NOT wired into the transport. For
+    /// production use, prefer `create_client_from_config()` which constructs
+    /// the transport with session tracking.
+    #[cfg(test)]
     pub fn new_with_config(config: McpServerConfig) -> Result<Self, ToolError> {
         if !matches!(
             config.effective_transport(),
@@ -214,7 +219,14 @@ impl McpClient {
         }
     }
 
-    /// Attach a session manager for Streamable HTTP session tracking.
+    /// Attach a session manager to the **client** only.
+    ///
+    /// **Warning:** This does NOT wire the session manager into the underlying
+    /// `HttpMcpTransport`, so the transport will not capture `Mcp-Session-Id`
+    /// from responses. For production use, construct the transport with
+    /// `HttpMcpTransport::with_session_manager()` and pass it to
+    /// `new_with_transport()` instead. See `create_client_from_config()`.
+    #[cfg(test)]
     pub fn with_session_manager(mut self, session_manager: Arc<McpSessionManager>) -> Self {
         self.session_manager = Some(session_manager);
         self
@@ -235,6 +247,12 @@ impl McpClient {
         self.session_manager.is_some()
     }
 
+    /// Get the underlying transport (test-only).
+    #[cfg(test)]
+    pub(crate) fn transport(&self) -> &Arc<dyn McpTransport> {
+        &self.transport
+    }
+
     /// Get the next request ID.
     fn next_request_id(&self) -> u64 {
         self.next_id.fetch_add(1, Ordering::SeqCst)
diff --git a/src/tools/mcp/factory.rs b/src/tools/mcp/factory.rs
index c31c5051..bbb09256 100644
--- a/src/tools/mcp/factory.rs
+++ b/src/tools/mcp/factory.rs
@@ -7,6 +7,7 @@ use std::sync::Arc;
 
 use crate::secrets::SecretsStore;
 use crate::tools::mcp::config::{EffectiveTransport, McpServerConfig};
+use crate::tools::mcp::http_transport::HttpMcpTransport;
 use crate::tools::mcp::{McpClient, McpProcessManager, McpSessionManager, McpTransport};
 
 /// Error returned when MCP client creation fails.
@@ -78,33 +79,37 @@ pub async fn create_client_from_config(
             Err(McpFactoryError::UnixNotSupported { name: server_name })
         }
         EffectiveTransport::Http => {
+            // Authenticated (OAuth) path: tokens exist or server requires auth.
             if let Some(ref secrets) = secrets {
                 let has_tokens =
                     crate::tools::mcp::is_authenticated(&server, secrets, user_id).await;
 
                 if has_tokens || server.requires_auth() {
-                    Ok(McpClient::new_authenticated(
+                    return Ok(McpClient::new_authenticated(
                         server,
                         Arc::clone(session_manager),
                         Arc::clone(secrets),
                         user_id,
-                    ))
-                } else {
-                    Ok(McpClient::new_with_config(server)
-                        .map_err(|e| McpFactoryError::InvalidConfig {
-                            name: server_name.clone(),
-                            reason: e.to_string(),
-                        })?
-                        .with_session_manager(Arc::clone(session_manager)))
+                    ));
                 }
-            } else {
-                Ok(McpClient::new_with_config(server)
-                    .map_err(|e| McpFactoryError::InvalidConfig {
-                        name: server_name,
-                        reason: e.to_string(),
-                    })?
-                    .with_session_manager(Arc::clone(session_manager)))
             }
+
+            // Non-OAuth HTTP: wire the session manager into the *transport* so
+            // it captures `Mcp-Session-Id` from responses. Passing it only to
+            // the client (via `with_session_manager`) is not enough — the
+            // transport must know about it to read/write the header.
+            let transport = Arc::new(
+                HttpMcpTransport::new(server.url.clone(), server.name.clone())
+                    .with_session_manager(Arc::clone(session_manager)),
+            );
+            Ok(McpClient::new_with_transport(
+                server.name.clone(),
+                transport,
+                Some(Arc::clone(session_manager)),
+                secrets,
+                user_id,
+                Some(server),
+            ))
         }
     }
 }
@@ -134,4 +139,84 @@ mod tests {
             "non-OAuth HTTP clients must carry a session manager"
         );
     }
+
+    /// Regression test: the factory must wire the session manager into the
+    /// *transport*, not just the client. Otherwise the transport never
+    /// captures `Mcp-Session-Id` from responses and subsequent requests
+    /// lack the header, causing the server to reject them.
+    #[tokio::test]
+    async fn test_factory_non_oauth_http_transport_captures_session_id() {
+        use axum::http::header::HeaderName;
+        use axum::{Router, http::StatusCode, response::IntoResponse, routing::post};
+        use tokio::net::TcpListener;
+
+        const SESSION_ID: &str = "test-session-abc123";
+
+        async fn session_echo() -> impl IntoResponse {
+            let body = serde_json::json!({
+                "jsonrpc": "2.0",
+                "id": 1,
+                "result": {}
+            })
+            .to_string();
+            (
+                StatusCode::OK,
+                [(
+                    HeaderName::from_static("mcp-session-id"),
+                    SESSION_ID.to_string(),
+                )],
+                body,
+            )
+        }
+
+        let app = Router::new().route("/", post(session_echo));
+        let listener = TcpListener::bind("127.0.0.1:0").await.unwrap();
+        let addr = listener.local_addr().unwrap();
+        let url = format!("http://127.0.0.1:{}", addr.port());
+
+        tokio::spawn(async move {
+            axum::serve(listener, app).await.unwrap();
+        });
+
+        let server = McpServerConfig::new("session-test", &url);
+        let session_manager = Arc::new(McpSessionManager::new());
+        let process_manager = Arc::new(McpProcessManager::new());
+
+        let client = create_client_from_config(
+            server,
+            &session_manager,
+            &process_manager,
+            None,
+            "test-user",
+        )
+        .await
+        .expect("factory should succeed for HTTP config");
+
+        // Pre-create a session entry so that update_session_id has something to update.
+        // In production, the MCP initialize handshake calls get_or_create before responses arrive.
+        session_manager.get_or_create("session-test", &url).await;
+
+        // Send a request through the client's transport to trigger session capture.
+        use crate::tools::mcp::protocol::McpRequest;
+        let request = McpRequest {
+            jsonrpc: "2.0".to_string(),
+            id: Some(1),
+            method: "test".to_string(),
+            params: Some(serde_json::json!({})),
+        };
+        let headers = std::collections::HashMap::new();
+        client
+            .transport()
+            .send(&request, &headers)
+            .await
+            .expect("request should succeed");
+
+        // Verify the session manager captured the session ID from the response.
+        let captured = session_manager.get_session_id("session-test").await;
+        assert_eq!(
+            captured.as_deref(),
+            Some(SESSION_ID),
+            "transport must capture Mcp-Session-Id into session manager"
+        );
+    }
 }
diff --git a/src/tools/mcp/http_transport.rs b/src/tools/mcp/http_transport.rs
index 59873ce4..ea3e1c03 100644
--- a/src/tools/mcp/http_transport.rs
+++ b/src/tools/mcp/http_transport.rs
@@ -494,6 +494,34 @@ mod tests {
         assert_eq!(echoed["authorization"], "Bearer oauth-token");
     }
 
+    /// Regression test for #1436: 202 Accepted responses for notifications
+    /// were parsed as JSON, causing "Failed to parse MCP response" errors
+    /// that broke the MCP session handshake.
+    #[tokio::test]
+    async fn test_wire_202_accepted_for_notification() {
+        use axum::{Router, http::StatusCode, routing::post};
+        use tokio::net::TcpListener;
+
+        async fn accept_notification() -> StatusCode {
+            StatusCode::ACCEPTED
+        }
+
+        let app = Router::new().route("/", post(accept_notification));
+        let listener = TcpListener::bind("127.0.0.1:0").await.unwrap();
+        let addr = listener.local_addr().unwrap();
+        let url = format!("http://127.0.0.1:{}", addr.port());
+
+        tokio::spawn(async move {
+            axum::serve(listener, app).await.unwrap();
+        });
+
+        let transport = HttpMcpTransport::new(&url, "test-202");
+        let request = McpRequest::initialized_notification();
+        let response = transport.send(&request, &HashMap::new()).await.unwrap();
+        assert!(response.result.is_none());
+        assert!(response.error.is_none());
+    }
+
     #[tokio::test]
     async fn test_wire_custom_auth_preserved_when_no_per_request_auth() {
         let (url, _handle) = spawn_echo_server().await;
diff --git a/src/tools/wasm/loader.rs b/src/tools/wasm/loader.rs
index 2a7ed040..4876dc1b 100644
--- a/src/tools/wasm/loader.rs
+++ b/src/tools/wasm/loader.rs
@@ -446,16 +446,14 @@ fn resolve_oauth_refresh_config(cap_file: &CapabilitiesFile) -> Option<OAuthRefr
         builtin.as_ref(),
         exchange_proxy_url.is_some(),
     );
-    let gateway_token = crate::config::helpers::env_or_override("GATEWAY_AUTH_TOKEN")
-        .map(|token| token.trim().to_string())
-        .filter(|token| !token.is_empty());
+    let oauth_proxy_auth_token = crate::cli::oauth_defaults::oauth_proxy_auth_token();
 
     Some(OAuthRefreshConfig {
         token_url: oauth.token_url.clone(),
         client_id,
         client_secret,
         exchange_proxy_url,
-        gateway_token,
+        gateway_token: oauth_proxy_auth_token,
         secret_name: auth.secret_name.clone(),
         provider: auth.provider.clone(),
     })
@@ -891,6 +889,11 @@ mod tests {
             AuthCapabilitySchema, CapabilitiesFile, OAuthConfigSchema,
         };
 
+        let _guard = lock_env();
+        let _proxy_guard = set_env_var("IRONCLAW_OAUTH_EXCHANGE_URL", None);
+        let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", None);
+        let _oauth_proxy_token_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", None);
+
         let caps = CapabilitiesFile {
             auth: Some(AuthCapabilitySchema {
                 secret_name: "google_oauth_token".to_string(),
@@ -982,6 +985,7 @@ mod tests {
         let _guard = lock_env();
         let _proxy_guard = set_env_var("IRONCLAW_OAUTH_EXCHANGE_URL", None);
         let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", None);
+        let _oauth_proxy_token_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", None);
 
         // google_oauth_token should fall back to built-in credentials
         let caps = CapabilitiesFile {
@@ -1021,6 +1025,7 @@ mod tests {
             Some("https://compose-api.example.com"),
         );
         let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-test-token"));
+        let _oauth_proxy_token_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", None);
         let _client_id_guard =
             set_env_var("GOOGLE_OAUTH_CLIENT_ID", Some("hosted-google-client-id"));
 
@@ -1061,6 +1066,7 @@ mod tests {
             Some("https://compose-api.example.com"),
         );
         let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-test-token"));
+        let _oauth_proxy_token_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", None);
         let _client_id_guard =
             set_env_var("GOOGLE_OAUTH_CLIENT_ID", Some("hosted-google-client-id"));
         let _client_secret_guard =
@@ -1095,6 +1101,47 @@ mod tests {
         assert_eq!(config.gateway_token.as_deref(), Some("gateway-test-token"));
     }
 
+    #[test]
+    fn test_resolve_oauth_refresh_config_hosted_proxy_prefers_dedicated_proxy_auth_token() {
+        use crate::tools::wasm::capabilities_schema::{
+            AuthCapabilitySchema, CapabilitiesFile, OAuthConfigSchema,
+        };
+
+        let _guard = lock_env();
+        let _proxy_guard = set_env_var(
+            "IRONCLAW_OAUTH_EXCHANGE_URL",
+            Some("https://compose-api.example.com"),
+        );
+        let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-test-token"));
+        let _oauth_proxy_token_guard = set_env_var(
+            "IRONCLAW_OAUTH_PROXY_AUTH_TOKEN",
+            Some("shared-oauth-proxy-secret"),
+        );
+        let _client_id_guard =
+            set_env_var("GOOGLE_OAUTH_CLIENT_ID", Some("hosted-google-client-id"));
+
+        let caps = CapabilitiesFile {
+            auth: Some(AuthCapabilitySchema {
+                secret_name: "google_oauth_token".to_string(),
+                provider: Some("google".to_string()),
+                oauth: Some(OAuthConfigSchema {
+                    authorization_url: "https://accounts.google.com/o/oauth2/v2/auth".to_string(),
+                    token_url: "https://oauth2.googleapis.com/token".to_string(),
+                    client_id_env: Some("GOOGLE_OAUTH_CLIENT_ID".to_string()),
+                    ..Default::default()
+                }),
+                ..Default::default()
+            }),
+            ..Default::default()
+        };
+
+        let config = super::resolve_oauth_refresh_config(&caps).expect("hosted oauth config");
+        assert_eq!(
+            config.gateway_token.as_deref(),
+            Some("shared-oauth-proxy-secret")
+        );
+    }
+
     // ---------------------------------------------------------------
     // Security regression tests
     // ---------------------------------------------------------------
diff --git a/src/tools/wasm/wrapper.rs b/src/tools/wasm/wrapper.rs
index 05508e97..bb9c4dd4 100644
--- a/src/tools/wasm/wrapper.rs
+++ b/src/tools/wasm/wrapper.rs
@@ -62,7 +62,8 @@ pub struct OAuthRefreshConfig {
     pub client_secret: Option<String>,
     /// Hosted OAuth proxy base URL (e.g., "http://host.docker.internal:8080").
     pub exchange_proxy_url: Option<String>,
-    /// Gateway auth token for authenticating with the hosted OAuth proxy.
+    /// OAuth proxy auth token for authenticating with the hosted OAuth proxy.
+    /// Kept as `gateway_token` for public API compatibility.
     pub gateway_token: Option<String>,
     /// Secret name of the access token (e.g., "google_oauth_token").
     /// The refresh token lives at `{secret_name}_refresh_token`.
@@ -71,6 +72,12 @@ pub struct OAuthRefreshConfig {
     pub provider: Option<String>,
 }
 
+impl OAuthRefreshConfig {
+    fn oauth_proxy_auth_token(&self) -> Option<&str> {
+        self.gateway_token.as_deref()
+    }
+}
+
 /// Pre-resolved credential for host-based injection.
 ///
 /// Built before each WASM execution by decrypting secrets from the store.
@@ -1218,9 +1225,9 @@ async fn refresh_oauth_token(
     let refresh_name = format!("{}_refresh_token", config.secret_name);
 
     if let Some(proxy_url) = config.exchange_proxy_url.as_deref() {
-        let Some(gateway_token) = config.gateway_token.as_deref() else {
+        let Some(oauth_proxy_auth_token) = config.oauth_proxy_auth_token() else {
             tracing::warn!(
-                "OAuth refresh proxy is configured, but no gateway auth token is available"
+                "OAuth refresh proxy is configured, but no OAuth proxy auth token is available"
             );
             return false;
         };
@@ -1235,7 +1242,7 @@ async fn refresh_oauth_token(
         let token_response = match oauth_defaults::refresh_token_via_proxy(
             oauth_defaults::ProxyRefreshTokenRequest {
                 proxy_url,
-                gateway_token,
+                gateway_token: oauth_proxy_auth_token,
                 token_url: &config.token_url,
                 client_id: &config.client_id,
                 client_secret: config.client_secret.as_deref(),
@@ -2704,7 +2711,8 @@ mod tests {
     }
 
     #[tokio::test]
-    async fn test_resolve_host_credentials_skips_refresh_token_lookup_without_gateway_token() {
+    async fn test_resolve_host_credentials_skips_refresh_token_lookup_without_oauth_proxy_auth_token()
+     {
         use crate::secrets::{
             CreateSecretParams, CredentialLocation, CredentialMapping, SecretsStore,
         };
diff --git a/tests/e2e_builtin_tool_coverage.rs b/tests/e2e_builtin_tool_coverage.rs
index 1c3cc6a2..7c0c7bc7 100644
--- a/tests/e2e_builtin_tool_coverage.rs
+++ b/tests/e2e_builtin_tool_coverage.rs
@@ -205,7 +205,44 @@ mod tests {
     }
 
     // -----------------------------------------------------------------------
-    // Test 5: routine_manual_create_defaults_to_tools_enabled
+    // Test 5: routine_update_fail_delete_fallback
+    // -----------------------------------------------------------------------
+
+    #[tokio::test]
+    async fn routine_update_fail_delete_fallback() {
+        let trace = LlmTrace::from_file(concat!(
+            env!("CARGO_MANIFEST_DIR"),
+            "/tests/fixtures/llm_traces/tools/routine_update_fail_delete_fallback.json"
+        ))
+        .expect("failed to load routine_update_fail_delete_fallback.json");
+
+        let rig = TestRigBuilder::new()
+            .with_trace(trace.clone())
+            .with_auto_approve_tools(true)
+            .build()
+            .await;
+
+        rig.send_message("Try converting a routine trigger, then recover by deleting it")
+            .await;
+        let responses = rig.wait_for_responses(1, Duration::from_secs(15)).await;
+
+        rig.verify_trace_expects(&trace, &responses);
+
+        let completed = rig.tool_calls_completed();
+        assert!(
+            completed.iter().any(|(n, ok)| n == "routine_update" && !ok),
+            "routine_update should fail in this regression path: {completed:?}"
+        );
+        assert!(
+            completed.iter().any(|(n, ok)| n == "routine_delete" && *ok),
+            "routine_delete should recover successfully via preserved routine identity: {completed:?}"
+        );
+
+        rig.shutdown();
+    }
+
+    // -----------------------------------------------------------------------
+    // Test 6: routine_manual_create_defaults_to_tools_enabled
     // -----------------------------------------------------------------------
 
     #[tokio::test]
@@ -246,7 +283,7 @@ mod tests {
     }
 
     // -----------------------------------------------------------------------
-    // Test 6: routine_manual_create_explicit_no_tools
+    // Test 7: routine_manual_create_explicit_no_tools
     // -----------------------------------------------------------------------
 
     #[tokio::test]
@@ -287,7 +324,7 @@ mod tests {
     }
 
     // -----------------------------------------------------------------------
-    // Test 7: routine_history
+    // Test 8: routine_history
     // -----------------------------------------------------------------------
 
     #[tokio::test]
diff --git a/tests/fixtures/llm_traces/tools/routine_update_fail_delete_fallback.json b/tests/fixtures/llm_traces/tools/routine_update_fail_delete_fallback.json
new file mode 100644
index 00000000..5c76dbb5
--- /dev/null
+++ b/tests/fixtures/llm_traces/tools/routine_update_fail_delete_fallback.json
@@ -0,0 +1,70 @@
+{
+  "model_name": "test-routine-update-fail-delete-fallback",
+  "expects": {
+    "tools_used": ["routine_create", "routine_update", "routine_delete"],
+    "tool_results_contain": {
+      "routine_update": "Cannot update schedule or timezone on a non-cron routine.",
+      "routine_delete": "temp-routine"
+    },
+    "min_responses": 1
+  },
+  "steps": [
+    {
+      "response": {
+        "type": "tool_calls",
+        "tool_calls": [
+          {
+            "id": "call_rc_fallback",
+            "name": "routine_create",
+            "arguments": {
+              "name": "temp-routine",
+              "trigger_type": "manual",
+              "prompt": "Temporary routine for fallback test."
+            }
+          }
+        ],
+        "input_tokens": 120,
+        "output_tokens": 40
+      }
+    },
+    {
+      "response": {
+        "type": "tool_calls",
+        "tool_calls": [
+          {
+            "id": "call_ru_fallback",
+            "name": "routine_update",
+            "arguments": {
+              "name": "temp-routine",
+              "schedule": "0 */10 * * * *"
+            }
+          }
+        ],
+        "input_tokens": 200,
+        "output_tokens": 30
+      }
+    },
+    {
+      "response": {
+        "type": "tool_calls",
+        "tool_calls": [
+          {
+            "id": "call_rd_fallback",
+            "name": "routine_delete",
+            "arguments": {}
+          }
+        ],
+        "input_tokens": 300,
+        "output_tokens": 20
+      }
+    },
+    {
+      "response": {
+        "type": "text",
+        "content": "I recovered from the failed update and cleaned up the original routine.",
+        "input_tokens": 380,
+        "output_tokens": 25
+      }
+    }
+  ]
+}