fix: default exec approvals to main agent (#1417) (thanks @czekaj)

When creating exec tools via chat/Discord, agentId was not passed,
causing allowlist lookup to use 'default' key instead of 'main'.
User's allowlist entries in agents.main were never matched.

Now derives agentId from sessionKey if not explicitly provided,
ensuring correct allowlist lookup for all exec paths.

CHANGELOG.md

@@ -5,11 +5,21 @@ Docs: https://docs.clawd.bot
 ## 2026.1.22
 
 ### Changes
+- Highlight: Lobster optional plugin tool for typed workflows + approval gates. https://docs.clawd.bot/tools/lobster
+- Memory: prevent CLI hangs by deferring vector probes, adding sqlite-vec/embedding timeouts, and showing sync progress early.
 - Docs: add troubleshooting entry for gateway.mode blocking gateway start. https://docs.clawd.bot/gateway/troubleshooting
+- Docs: add per-message Gmail search example for gog. (#1220) Thanks @mbelinky.
 - Onboarding: remove the run setup-token auth option (paste setup-token or reuse CLI creds instead).
+- Signal: add typing indicators and DM read receipts via signal-cli.
+- MSTeams: add file uploads, adaptive cards, and attachment handling improvements. (#1410) Thanks @Evizero.
 
 ### Fixes
+- Config: avoid stack traces for invalid configs and log the config path.
 - Doctor: warn when gateway.mode is unset with configure/config guidance.
+- macOS: include Textual syntax highlighting resources in packaged app to prevent chat crashes. (#1362)
+- Cron: cap reminder context history to 10 messages and honor `contextMessages`. (#1103) Thanks @mkbehr.
+- Exec approvals: treat main as the default agent + migrate legacy default allowlists. (#1417) Thanks @czekaj.
+- UI: refresh debug panel on route-driven tab changes. (#1373) Thanks @yazinsai.
 
 ## 2026.1.21
 

README.md

@@ -471,30 +471,34 @@ by Peter Steinberger and the community.
 See [CONTRIBUTING.md](CONTRIBUTING.md) for guidelines, maintainers, and how to submit PRs.  
 AI/vibe-coded PRs welcome! 🤖
 
+Special thanks to [Mario Zechner](https://mariozechner.at/) for his support and for
+[pi-mono](https://github.com/badlogic/pi-mono).
+
 Thanks to all clawtributors:
 
 <p align="left">
   <a href="https://github.com/steipete"><img src="https://avatars.githubusercontent.com/u/58493?v=4&s=48" width="48" height="48" alt="steipete" title="steipete"/></a> <a href="https://github.com/bohdanpodvirnyi"><img src="https://avatars.githubusercontent.com/u/31819391?v=4&s=48" width="48" height="48" alt="bohdanpodvirnyi" title="bohdanpodvirnyi"/></a> <a href="https://github.com/joaohlisboa"><img src="https://avatars.githubusercontent.com/u/8200873?v=4&s=48" width="48" height="48" alt="joaohlisboa" title="joaohlisboa"/></a> <a href="https://github.com/mneves75"><img src="https://avatars.githubusercontent.com/u/2423436?v=4&s=48" width="48" height="48" alt="mneves75" title="mneves75"/></a> <a href="https://github.com/MatthieuBizien"><img src="https://avatars.githubusercontent.com/u/173090?v=4&s=48" width="48" height="48" alt="MatthieuBizien" title="MatthieuBizien"/></a> <a href="https://github.com/MaudeBot"><img src="https://avatars.githubusercontent.com/u/255777700?v=4&s=48" width="48" height="48" alt="MaudeBot" title="MaudeBot"/></a> <a href="https://github.com/rahthakor"><img src="https://avatars.githubusercontent.com/u/8470553?v=4&s=48" width="48" height="48" alt="rahthakor" title="rahthakor"/></a> <a href="https://github.com/vrknetha"><img src="https://avatars.githubusercontent.com/u/20596261?v=4&s=48" width="48" height="48" alt="vrknetha" title="vrknetha"/></a> <a href="https://github.com/radek-paclt"><img src="https://avatars.githubusercontent.com/u/50451445?v=4&s=48" width="48" height="48" alt="radek-paclt" title="radek-paclt"/></a> <a href="https://github.com/joshp123"><img src="https://avatars.githubusercontent.com/u/1497361?v=4&s=48" width="48" height="48" alt="joshp123" title="joshp123"/></a>
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+  <a href="https://github.com/jverdi"><img src="https://avatars.githubusercontent.com/u/345050?v=4&s=48" width="48" height="48" alt="jverdi" title="jverdi"/></a> <a href="https://github.com/longmaba"><img src="https://avatars.githubusercontent.com/u/9361500?v=4&s=48" width="48" height="48" alt="longmaba" title="longmaba"/></a> <a href="https://github.com/mickahouan"><img src="https://avatars.githubusercontent.com/u/31423109?v=4&s=48" width="48" height="48" alt="mickahouan" title="mickahouan"/></a> <a href="https://github.com/mjrussell"><img src="https://avatars.githubusercontent.com/u/1641895?v=4&s=48" width="48" height="48" alt="mjrussell" title="mjrussell"/></a> <a href="https://github.com/p6l-richard"><img src="https://avatars.githubusercontent.com/u/18185649?v=4&s=48" width="48" height="48" alt="p6l-richard" title="p6l-richard"/></a> <a href="https://github.com/philipp-spiess"><img src="https://avatars.githubusercontent.com/u/458591?v=4&s=48" width="48" height="48" alt="philipp-spiess" title="philipp-spiess"/></a> <a href="https://github.com/robaxelsen"><img src="https://avatars.githubusercontent.com/u/13132899?v=4&s=48" width="48" height="48" alt="robaxelsen" title="robaxelsen"/></a> <a href="https://github.com/search?q=Sash%20Catanzarite"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Sash Catanzarite" title="Sash Catanzarite"/></a> <a href="https://github.com/T5-AndyML"><img src="https://avatars.githubusercontent.com/u/22801233?v=4&s=48" width="48" height="48" alt="T5-AndyML" title="T5-AndyML"/></a> <a href="https://github.com/search?q=VAC"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="VAC" title="VAC"/></a>
+  <a href="https://github.com/zknicker"><img src="https://avatars.githubusercontent.com/u/1164085?v=4&s=48" width="48" height="48" alt="zknicker" title="zknicker"/></a> <a href="https://github.com/search?q=alejandro%20maza"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="alejandro maza" title="alejandro maza"/></a> <a href="https://github.com/andrewting19"><img src="https://avatars.githubusercontent.com/u/10536704?v=4&s=48" width="48" height="48" alt="andrewting19" title="andrewting19"/></a> <a href="https://github.com/search?q=Andrii"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Andrii" title="Andrii"/></a> <a href="https://github.com/anpoirier"><img src="https://avatars.githubusercontent.com/u/1245729?v=4&s=48" width="48" height="48" alt="anpoirier" title="anpoirier"/></a> <a href="https://github.com/Asleep123"><img src="https://avatars.githubusercontent.com/u/122379135?v=4&s=48" width="48" height="48" alt="Asleep123" title="Asleep123"/></a> <a href="https://github.com/bolismauro"><img src="https://avatars.githubusercontent.com/u/771999?v=4&s=48" width="48" height="48" alt="bolismauro" title="bolismauro"/></a> <a href="https://github.com/conhecendocontato"><img src="https://avatars.githubusercontent.com/u/82890727?v=4&s=48" width="48" height="48" alt="conhecendocontato" title="conhecendocontato"/></a> <a href="https://github.com/czekaj"><img src="https://avatars.githubusercontent.com/u/1464539?v=4&s=48" width="48" height="48" alt="czekaj" title="czekaj"/></a> <a href="https://github.com/search?q=Dimitrios%20Ploutarchos"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Dimitrios Ploutarchos" title="Dimitrios Ploutarchos"/></a>
+  <a href="https://github.com/search?q=Drake%20Thomsen"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Drake Thomsen" title="Drake Thomsen"/></a> <a href="https://github.com/search?q=Felix%20Krause"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Felix Krause" title="Felix Krause"/></a> <a href="https://github.com/gtsifrikas"><img src="https://avatars.githubusercontent.com/u/8904378?v=4&s=48" width="48" height="48" alt="gtsifrikas" title="gtsifrikas"/></a> <a href="https://github.com/HazAT"><img src="https://avatars.githubusercontent.com/u/363802?v=4&s=48" width="48" height="48" alt="HazAT" title="HazAT"/></a> <a href="https://github.com/hrdwdmrbl"><img src="https://avatars.githubusercontent.com/u/554881?v=4&s=48" width="48" height="48" alt="hrdwdmrbl" title="hrdwdmrbl"/></a> <a href="https://github.com/hugobarauna"><img src="https://avatars.githubusercontent.com/u/2719?v=4&s=48" width="48" height="48" alt="hugobarauna" title="hugobarauna"/></a> <a href="https://github.com/search?q=Jamie%20Openshaw"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Jamie Openshaw" title="Jamie Openshaw"/></a> <a href="https://github.com/search?q=Jarvis"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Jarvis" title="Jarvis"/></a> <a href="https://github.com/search?q=Jefferson%20Nunn"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Jefferson Nunn" title="Jefferson Nunn"/></a> <a href="https://github.com/search?q=Kevin%20Lin"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Kevin Lin" title="Kevin Lin"/></a>
+  <a href="https://github.com/kitze"><img src="https://avatars.githubusercontent.com/u/1160594?v=4&s=48" width="48" height="48" alt="kitze" title="kitze"/></a> <a href="https://github.com/levifig"><img src="https://avatars.githubusercontent.com/u/1605?v=4&s=48" width="48" height="48" alt="levifig" title="levifig"/></a> <a href="https://github.com/search?q=Lloyd"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Lloyd" title="Lloyd"/></a> <a href="https://github.com/loukotal"><img src="https://avatars.githubusercontent.com/u/18210858?v=4&s=48" width="48" height="48" alt="loukotal" title="loukotal"/></a> <a href="https://github.com/martinpucik"><img src="https://avatars.githubusercontent.com/u/5503097?v=4&s=48" width="48" height="48" alt="martinpucik" title="martinpucik"/></a> <a href="https://github.com/search?q=Miles"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Miles" title="Miles"/></a> <a href="https://github.com/mrdbstn"><img src="https://avatars.githubusercontent.com/u/58957632?v=4&s=48" width="48" height="48" alt="mrdbstn" title="mrdbstn"/></a> <a href="https://github.com/MSch"><img src="https://avatars.githubusercontent.com/u/7475?v=4&s=48" width="48" height="48" alt="MSch" title="MSch"/></a> <a href="https://github.com/search?q=Mustafa%20Tag%20Eldeen"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Mustafa Tag Eldeen" title="Mustafa Tag Eldeen"/></a> <a href="https://github.com/ndraiman"><img src="https://avatars.githubusercontent.com/u/12609607?v=4&s=48" width="48" height="48" alt="ndraiman" title="ndraiman"/></a>
+  <a href="https://github.com/nexty5870"><img src="https://avatars.githubusercontent.com/u/3869659?v=4&s=48" width="48" height="48" alt="nexty5870" title="nexty5870"/></a> <a href="https://github.com/odysseus0"><img src="https://avatars.githubusercontent.com/u/8635094?v=4&s=48" width="48" height="48" alt="odysseus0" title="odysseus0"/></a> <a href="https://github.com/prathamdby"><img src="https://avatars.githubusercontent.com/u/134331217?v=4&s=48" width="48" height="48" alt="prathamdby" title="prathamdby"/></a> <a href="https://github.com/ptn1411"><img src="https://avatars.githubusercontent.com/u/57529765?v=4&s=48" width="48" height="48" alt="ptn1411" title="ptn1411"/></a> <a href="https://github.com/reeltimeapps"><img src="https://avatars.githubusercontent.com/u/637338?v=4&s=48" width="48" height="48" alt="reeltimeapps" title="reeltimeapps"/></a> <a href="https://github.com/RLTCmpe"><img src="https://avatars.githubusercontent.com/u/10762242?v=4&s=48" width="48" height="48" alt="RLTCmpe" title="RLTCmpe"/></a> <a href="https://github.com/rodrigouroz"><img src="https://avatars.githubusercontent.com/u/384037?v=4&s=48" width="48" height="48" alt="rodrigouroz" title="rodrigouroz"/></a> <a href="https://github.com/search?q=Rolf%20Fredheim"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Rolf Fredheim" title="Rolf Fredheim"/></a> <a href="https://github.com/search?q=Rony%20Kelner"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Rony Kelner" title="Rony Kelner"/></a> <a href="https://github.com/search?q=Samrat%20Jha"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Samrat Jha" title="Samrat Jha"/></a>
+  <a href="https://github.com/siraht"><img src="https://avatars.githubusercontent.com/u/73152895?v=4&s=48" width="48" height="48" alt="siraht" title="siraht"/></a> <a href="https://github.com/snopoke"><img src="https://avatars.githubusercontent.com/u/249606?v=4&s=48" width="48" height="48" alt="snopoke" title="snopoke"/></a> <a href="https://github.com/search?q=The%20Admiral"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="The Admiral" title="The Admiral"/></a> <a href="https://github.com/thesash"><img src="https://avatars.githubusercontent.com/u/1166151?v=4&s=48" width="48" height="48" alt="thesash" title="thesash"/></a> <a href="https://github.com/search?q=Ubuntu"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Ubuntu" title="Ubuntu"/></a> <a href="https://github.com/voidserf"><img src="https://avatars.githubusercontent.com/u/477673?v=4&s=48" width="48" height="48" alt="voidserf" title="voidserf"/></a> <a href="https://github.com/search?q=Vultr-Clawd%20Admin"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Vultr-Clawd Admin" title="Vultr-Clawd Admin"/></a> <a href="https://github.com/search?q=Wimmie"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Wimmie" title="Wimmie"/></a> <a href="https://github.com/wstock"><img src="https://avatars.githubusercontent.com/u/1394687?v=4&s=48" width="48" height="48" alt="wstock" title="wstock"/></a> <a href="https://github.com/yazinsai"><img src="https://avatars.githubusercontent.com/u/1846034?v=4&s=48" width="48" height="48" alt="yazinsai" title="yazinsai"/></a>
+  <a href="https://github.com/search?q=Zach%20Knickerbocker"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Zach Knickerbocker" title="Zach Knickerbocker"/></a> <a href="https://github.com/Alphonse-arianee"><img src="https://avatars.githubusercontent.com/u/254457365?v=4&s=48" width="48" height="48" alt="Alphonse-arianee" title="Alphonse-arianee"/></a> <a href="https://github.com/search?q=Azade"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Azade" title="Azade"/></a> <a href="https://github.com/carlulsoe"><img src="https://avatars.githubusercontent.com/u/34673973?v=4&s=48" width="48" height="48" alt="carlulsoe" title="carlulsoe"/></a> <a href="https://github.com/search?q=ddyo"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="ddyo" title="ddyo"/></a> <a href="https://github.com/search?q=Erik"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Erik" title="Erik"/></a> <a href="https://github.com/latitudeki5223"><img src="https://avatars.githubusercontent.com/u/119656367?v=4&s=48" width="48" height="48" alt="latitudeki5223" title="latitudeki5223"/></a> <a href="https://github.com/search?q=Manuel%20Maly"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Manuel Maly" title="Manuel Maly"/></a> <a href="https://github.com/search?q=Mourad%20Boustani"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Mourad Boustani" title="Mourad Boustani"/></a> <a href="https://github.com/odrobnik"><img src="https://avatars.githubusercontent.com/u/333270?v=4&s=48" width="48" height="48" alt="odrobnik" title="odrobnik"/></a>
+  <a href="https://github.com/pcty-nextgen-ios-builder"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="pcty-nextgen-ios-builder" title="pcty-nextgen-ios-builder"/></a> <a href="https://github.com/search?q=Quentin"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Quentin" title="Quentin"/></a> <a href="https://github.com/search?q=Randy%20Torres"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="Randy Torres" title="Randy Torres"/></a> <a href="https://github.com/rhjoh"><img src="https://avatars.githubusercontent.com/u/105699450?v=4&s=48" width="48" height="48" alt="rhjoh" title="rhjoh"/></a> <a href="https://github.com/ronak-guliani"><img src="https://avatars.githubusercontent.com/u/23518228?v=4&s=48" width="48" height="48" alt="ronak-guliani" title="ronak-guliani"/></a> <a href="https://github.com/search?q=William%20Stock"><img src="assets/avatar-placeholder.svg" width="48" height="48" alt="William Stock" title="William Stock"/></a>
 </p>

appcast.xml

@@ -3,13 +3,13 @@
     <channel>
         <title>Clawdbot</title>
         <item>
-            <title>2026.1.20</title>
+            <title>2026.1.21</title>
             <pubDate>Wed, 21 Jan 2026 08:18:22 +0000</pubDate>
             <link>https://raw.githubusercontent.com/clawdbot/clawdbot/main/appcast.xml</link>
             <sparkle:version>7116</sparkle:version>
-            <sparkle:shortVersionString>2026.1.20</sparkle:shortVersionString>
+            <sparkle:shortVersionString>2026.1.21</sparkle:shortVersionString>
             <sparkle:minimumSystemVersion>15.0</sparkle:minimumSystemVersion>
-            <description><![CDATA[<h2>Clawdbot 2026.1.20</h2>
+            <description><![CDATA[<h2>Clawdbot 2026.1.21</h2>
 <h3>Changes</h3>
 <ul>
 <li>Control UI: add copy-as-markdown with error feedback. (#1345) https://docs.clawd.bot/web/control-ui</li>
@@ -190,7 +190,7 @@
 Thanks @AlexMikhalev, @CoreyH, @John-Rood, @KrauseFx, @MaudeBot, @Nachx639, @NicholaiVogel, @RyanLisse, @ThePickle31, @VACInc, @Whoaa512, @YuriNachos, @aaronveklabs, @abdaraxus, @alauppe, @ameno-, @artuskg, @austinm911, @bradleypriest, @cheeeee, @dougvk, @fogboots, @gnarco, @gumadeiras, @jdrhyne, @joelklabo, @longmaba, @mukhtharcm, @odysseus0, @oscargavin, @rhjoh, @sebslight, @sibbl, @sleontenko, @steipete, @suminhthanh, @thewilloftheshadow, @tyler6204, @vignesh07, @visionik, @ysqander, @zerone0x.
 <p><a href="https://github.com/clawdbot/clawdbot/blob/main/CHANGELOG.md">View full changelog</a></p>
 ]]></description>
-            <enclosure url="https://github.com/clawdbot/clawdbot/releases/download/v2026.1.20/Clawdbot-2026.1.20.zip" length="12208102" type="application/octet-stream" sparkle:edSignature="hU495Eii8O3qmmUnxYFhXyEGv+qan6KL+GpeuBhPIXf+7B5F/gBh5Oz9cHaqaAPoZ4/3Bo6xgvic0HTkbz6gDw=="/>
+            <enclosure url="https://github.com/clawdbot/clawdbot/releases/download/v2026.1.21/Clawdbot-2026.1.21.zip" length="12208102" type="application/octet-stream" sparkle:edSignature="hU495Eii8O3qmmUnxYFhXyEGv+qan6KL+GpeuBhPIXf+7B5F/gBh5Oz9cHaqaAPoZ4/3Bo6xgvic0HTkbz6gDw=="/>
         </item>
         <item>
             <title>2026.1.16-2</title>
@@ -290,4 +290,4 @@ Thanks @AlexMikhalev, @CoreyH, @John-Rood, @KrauseFx, @MaudeBot, @Nachx639, @Nic
             <enclosure url="https://github.com/clawdbot/clawdbot/releases/download/v2026.1.15/Clawdbot-2026.1.15.zip" length="12127276" type="application/octet-stream" sparkle:edSignature="o79vwTbtW/d91NQFRVfUDhsv6D4zIw7IkhY0N1iLImMu94BURgLcecA6z7Smy3bMobPwOyzN8yfm6mA/Rt8FCA=="/>
         </item>
     </channel>
-</rss>
+</rss>

apps/android/app/build.gradle.kts

@@ -21,8 +21,8 @@ android {
     applicationId = "com.clawdbot.android"
     minSdk = 31
     targetSdk = 36
-    versionCode = 202601200
-    versionName = "2026.1.20"
+    versionCode = 202601210
+    versionName = "2026.1.21"
   }
 
   buildTypes {

apps/ios/Sources/Info.plist

@@ -19,9 +19,9 @@
 	<key>CFBundlePackageType</key>
 	<string>APPL</string>
 	<key>CFBundleShortVersionString</key>
-	<string>2026.1.20</string>
+	<string>2026.1.21</string>
 	<key>CFBundleVersion</key>
-	<string>20260120</string>
+	<string>20260121</string>
 	<key>NSAppTransportSecurity</key>
 	<dict>
 		<key>NSAllowsArbitraryLoadsInWebContent</key>

apps/ios/Tests/Info.plist

@@ -17,8 +17,8 @@
 	<key>CFBundlePackageType</key>
 	<string>BNDL</string>
 	<key>CFBundleShortVersionString</key>
-	<string>2026.1.20</string>
+	<string>2026.1.21</string>
 	<key>CFBundleVersion</key>
-	<string>20260120</string>
+	<string>20260121</string>
 </dict>
 </plist>

apps/ios/project.yml

@@ -81,8 +81,8 @@ targets:
       properties:
         CFBundleDisplayName: Clawdbot
         CFBundleIconName: AppIcon
-        CFBundleShortVersionString: "2026.1.20"
-        CFBundleVersion: "20260120"
+        CFBundleShortVersionString: "2026.1.21"
+        CFBundleVersion: "20260121"
         UILaunchScreen: {}
         UIApplicationSceneManifest:
           UIApplicationSupportsMultipleScenes: false
@@ -130,5 +130,5 @@ targets:
       path: Tests/Info.plist
       properties:
         CFBundleDisplayName: ClawdbotTests
-        CFBundleShortVersionString: "2026.1.20"
-        CFBundleVersion: "20260120"
+        CFBundleShortVersionString: "2026.1.21"
+        CFBundleVersion: "20260121"

apps/macos/Sources/Clawdbot/ConnectionModeCoordinator.swift

@@ -6,15 +6,20 @@ final class ConnectionModeCoordinator {
     static let shared = ConnectionModeCoordinator()
 
     private let logger = Logger(subsystem: "com.clawdbot", category: "connection")
+    private var lastMode: AppState.ConnectionMode?
 
     /// Apply the requested connection mode by starting/stopping local gateway,
     /// managing the control-channel SSH tunnel, and cleaning up chat windows/panels.
     func apply(mode: AppState.ConnectionMode, paused: Bool) async {
+        if let lastMode = self.lastMode, lastMode != mode {
+            GatewayProcessManager.shared.clearLastFailure()
+            NodesStore.shared.lastError = nil
+        }
+        self.lastMode = mode
         switch mode {
         case .unconfigured:
-            if let error = await NodeServiceManager.stop() {
-                NodesStore.shared.lastError = "Node service stop failed: \(error)"
-            }
+            _ = await NodeServiceManager.stop()
+            NodesStore.shared.lastError = nil
             await RemoteTunnelManager.shared.stopAll()
             WebChatManager.shared.resetTunnels()
             GatewayProcessManager.shared.stop()
@@ -23,9 +28,8 @@ final class ConnectionModeCoordinator {
             Task.detached { await PortGuardian.shared.sweep(mode: .unconfigured) }
 
         case .local:
-            if let error = await NodeServiceManager.stop() {
-                NodesStore.shared.lastError = "Node service stop failed: \(error)"
-            }
+            _ = await NodeServiceManager.stop()
+            NodesStore.shared.lastError = nil
             await RemoteTunnelManager.shared.stopAll()
             WebChatManager.shared.resetTunnels()
             let shouldStart = GatewayAutostartPolicy.shouldStartGateway(mode: .local, paused: paused)
@@ -56,6 +60,7 @@ final class ConnectionModeCoordinator {
             WebChatManager.shared.resetTunnels()
 
             do {
+                NodesStore.shared.lastError = nil
                 if let error = await NodeServiceManager.start() {
                     NodesStore.shared.lastError = "Node service start failed: \(error)"
                 }

apps/macos/Sources/Clawdbot/GatewayProcessManager.swift

@@ -42,10 +42,20 @@ final class GatewayProcessManager {
     private var environmentRefreshTask: Task<Void, Never>?
     private var lastEnvironmentRefresh: Date?
     private var logRefreshTask: Task<Void, Never>?
+    #if DEBUG
+    private var testingConnection: GatewayConnection?
+    #endif
     private let logger = Logger(subsystem: "com.clawdbot", category: "gateway.process")
 
     private let logLimit = 20000 // characters to keep in-memory
     private let environmentRefreshMinInterval: TimeInterval = 30
+    private var connection: GatewayConnection {
+        #if DEBUG
+        return self.testingConnection ?? .shared
+        #else
+        return .shared
+        #endif
+    }
 
     func setActive(_ active: Bool) {
         // Remote mode should never spawn a local gateway; treat as stopped.
@@ -126,6 +136,10 @@ final class GatewayProcessManager {
         }
     }
 
+    func clearLastFailure() {
+        self.lastFailureReason = nil
+    }
+
     func refreshEnvironmentStatus(force: Bool = false) {
         let now = Date()
         if !force {
@@ -178,7 +192,7 @@ final class GatewayProcessManager {
         let hasListener = instance != nil
 
         let attemptAttach = {
-            try await GatewayConnection.shared.requestRaw(method: .health, timeoutMs: 2000)
+            try await self.connection.requestRaw(method: .health, timeoutMs: 2000)
         }
 
         for attempt in 0..<(hasListener ? 3 : 1) {
@@ -187,6 +201,7 @@ final class GatewayProcessManager {
                 let snap = decodeHealthSnapshot(from: data)
                 let details = self.describe(details: instanceText, port: port, snap: snap)
                 self.existingGatewayDetails = details
+                self.clearLastFailure()
                 self.status = .attachedExisting(details: details)
                 self.appendLog("[gateway] using existing instance: \(details)\n")
                 self.logger.info("gateway using existing instance details=\(details)")
@@ -310,9 +325,10 @@ final class GatewayProcessManager {
         while Date() < deadline {
             if !self.desiredActive { return }
             do {
-                _ = try await GatewayConnection.shared.requestRaw(method: .health, timeoutMs: 1500)
+                _ = try await self.connection.requestRaw(method: .health, timeoutMs: 1500)
                 let instance = await PortGuardian.shared.describe(port: port)
                 let details = instance.map { "pid \($0.pid)" }
+                self.clearLastFailure()
                 self.status = .running(details: details)
                 self.logger.info("gateway started details=\(details ?? "ok")")
                 self.refreshControlChannelIfNeeded(reason: "gateway started")
@@ -352,7 +368,8 @@ final class GatewayProcessManager {
         while Date() < deadline {
             if !self.desiredActive { return false }
             do {
-                _ = try await GatewayConnection.shared.requestRaw(method: .health, timeoutMs: 1500)
+                _ = try await self.connection.requestRaw(method: .health, timeoutMs: 1500)
+                self.clearLastFailure()
                 return true
             } catch {
                 try? await Task.sleep(nanoseconds: 300_000_000)
@@ -385,3 +402,19 @@ final class GatewayProcessManager {
         return String(text.suffix(limit))
     }
 }
+
+#if DEBUG
+extension GatewayProcessManager {
+    func setTestingConnection(_ connection: GatewayConnection?) {
+        self.testingConnection = connection
+    }
+
+    func setTestingDesiredActive(_ active: Bool) {
+        self.desiredActive = active
+    }
+
+    func setTestingLastFailureReason(_ reason: String?) {
+        self.lastFailureReason = reason
+    }
+}
+#endif

apps/macos/Sources/Clawdbot/Resources/Info.plist

@@ -15,9 +15,9 @@
     <key>CFBundlePackageType</key>
     <string>APPL</string>
     <key>CFBundleShortVersionString</key>
-    <string>2026.1.20</string>
+    <string>2026.1.21</string>
     <key>CFBundleVersion</key>
-    <string>202601200</string>
+    <string>202601210</string>
     <key>CFBundleIconFile</key>
     <string>Clawdbot</string>
     <key>CFBundleURLTypes</key>

apps/macos/Tests/ClawdbotIPCTests/GatewayProcessManagerTests.swift

@@ -0,0 +1,146 @@
+import Foundation
+import os
+import Testing
+@testable import Clawdbot
+
+@Suite(.serialized)
+@MainActor
+struct GatewayProcessManagerTests {
+    private final class FakeWebSocketTask: WebSocketTasking, @unchecked Sendable {
+        private let connectRequestID = OSAllocatedUnfairLock<String?>(initialState: nil)
+        private let pendingReceiveHandler =
+            OSAllocatedUnfairLock<(@Sendable (Result<URLSessionWebSocketTask.Message, Error>)
+                    -> Void)?>(initialState: nil)
+        private let cancelCount = OSAllocatedUnfairLock(initialState: 0)
+        private let sendCount = OSAllocatedUnfairLock(initialState: 0)
+
+        var state: URLSessionTask.State = .suspended
+
+        func resume() {
+            self.state = .running
+        }
+
+        func cancel(with closeCode: URLSessionWebSocketTask.CloseCode, reason: Data?) {
+            _ = (closeCode, reason)
+            self.state = .canceling
+            self.cancelCount.withLock { $0 += 1 }
+            let handler = self.pendingReceiveHandler.withLock { handler in
+                defer { handler = nil }
+                return handler
+            }
+            handler?(Result<URLSessionWebSocketTask.Message, Error>.failure(URLError(.cancelled)))
+        }
+
+        func send(_ message: URLSessionWebSocketTask.Message) async throws {
+            let currentSendCount = self.sendCount.withLock { count in
+                defer { count += 1 }
+                return count
+            }
+
+            if currentSendCount == 0 {
+                guard case let .data(data) = message else { return }
+                if let obj = try? JSONSerialization.jsonObject(with: data) as? [String: Any],
+                   (obj["type"] as? String) == "req",
+                   (obj["method"] as? String) == "connect",
+                   let id = obj["id"] as? String
+                {
+                    self.connectRequestID.withLock { $0 = id }
+                }
+                return
+            }
+
+            guard case let .data(data) = message else { return }
+            guard
+                let obj = try? JSONSerialization.jsonObject(with: data) as? [String: Any],
+                (obj["type"] as? String) == "req",
+                let id = obj["id"] as? String
+            else {
+                return
+            }
+
+            let response = Self.responseData(id: id)
+            let handler = self.pendingReceiveHandler.withLock { $0 }
+            handler?(Result<URLSessionWebSocketTask.Message, Error>.success(.data(response)))
+        }
+
+        func receive() async throws -> URLSessionWebSocketTask.Message {
+            let id = self.connectRequestID.withLock { $0 } ?? "connect"
+            return .data(Self.connectOkData(id: id))
+        }
+
+        func receive(
+            completionHandler: @escaping @Sendable (Result<URLSessionWebSocketTask.Message, Error>) -> Void)
+        {
+            self.pendingReceiveHandler.withLock { $0 = completionHandler }
+        }
+
+        private static func connectOkData(id: String) -> Data {
+            let json = """
+            {
+              "type": "res",
+              "id": "\(id)",
+              "ok": true,
+              "payload": {
+                "type": "hello-ok",
+                "protocol": 2,
+                "server": { "version": "test", "connId": "test" },
+                "features": { "methods": [], "events": [] },
+                "snapshot": {
+                  "presence": [ { "ts": 1 } ],
+                  "health": {},
+                  "stateVersion": { "presence": 0, "health": 0 },
+                  "uptimeMs": 0
+                },
+                "policy": { "maxPayload": 1, "maxBufferedBytes": 1, "tickIntervalMs": 30000 }
+              }
+            }
+            """
+            return Data(json.utf8)
+        }
+
+        private static func responseData(id: String) -> Data {
+            let json = """
+            {
+              "type": "res",
+              "id": "\(id)",
+              "ok": true,
+              "payload": { "ok": true }
+            }
+            """
+            return Data(json.utf8)
+        }
+    }
+
+    private final class FakeWebSocketSession: WebSocketSessioning, @unchecked Sendable {
+        private let tasks = OSAllocatedUnfairLock(initialState: [FakeWebSocketTask]())
+
+        func makeWebSocketTask(url: URL) -> WebSocketTaskBox {
+            _ = url
+            let task = FakeWebSocketTask()
+            self.tasks.withLock { $0.append(task) }
+            return WebSocketTaskBox(task: task)
+        }
+    }
+
+    @Test func clearsLastFailureWhenHealthSucceeds() async {
+        let session = FakeWebSocketSession()
+        let url = URL(string: "ws://example.invalid")!
+        let connection = GatewayConnection(
+            configProvider: { (url: url, token: nil, password: nil) },
+            sessionBox: WebSocketSessionBox(session: session))
+
+        let manager = GatewayProcessManager.shared
+        manager.setTestingConnection(connection)
+        manager.setTestingDesiredActive(true)
+        manager.setTestingLastFailureReason("health failed")
+        defer {
+            manager.setTestingConnection(nil)
+            manager.setTestingDesiredActive(false)
+            manager.setTestingLastFailureReason(nil)
+        }
+
+        let ready = await manager.waitForGatewayReady(timeout: 0.5)
+        #expect(ready)
+        #expect(manager.lastFailureReason == nil)
+    }
+}

docs/channels/msteams.md

@@ -8,9 +8,9 @@ read_when:
 > "Abandon all hope, ye who enter here."
 
 
-Updated: 2026-01-16
+Updated: 2026-01-21
 
-Status: text + DM attachments are supported; channel/group attachments require Microsoft Graph permissions. Polls are sent via Adaptive Cards.
+Status: text + DM attachments are supported; channel/group file sending requires `sharePointSiteId` + Graph permissions (see [Sending files in group chats](#sending-files-in-group-chats)). Polls are sent via Adaptive Cards.
 
 ## Plugin required
 Microsoft Teams ships as a plugin and is not bundled with the core install.
@@ -403,7 +403,7 @@ Clawdbot handles this by returning quickly and sending replies proactively, but
 Teams markdown is more limited than Slack or Discord:
 - Basic formatting works: **bold**, *italic*, `code`, links
 - Complex markdown (tables, nested lists) may not render correctly
-- Adaptive Cards are used for polls; other card types are not yet supported
+- Adaptive Cards are supported for polls and arbitrary card sends (see below)
 
 ## Configuration
 Key settings (see `/gateway/configuration` for shared channel patterns):
@@ -422,6 +422,7 @@ Key settings (see `/gateway/configuration` for shared channel patterns):
 - `channels.msteams.teams.<teamId>.requireMention`: per-team override.
 - `channels.msteams.teams.<teamId>.channels.<conversationId>.replyStyle`: per-channel override.
 - `channels.msteams.teams.<teamId>.channels.<conversationId>.requireMention`: per-channel override.
+- `channels.msteams.sharePointSiteId`: SharePoint site ID for file uploads in group chats/channels (see [Sending files in group chats](#sending-files-in-group-chats)).
 
 ## Routing & Sessions
 - Session keys follow the standard agent format (see [/concepts/session](/concepts/session)):
@@ -471,6 +472,75 @@ Teams recently introduced two channel UI styles over the same underlying data mo
 Without Graph permissions, channel messages with images will be received as text-only (the image content is not accessible to the bot).
 By default, Clawdbot only downloads media from Microsoft/Teams hostnames. Override with `channels.msteams.mediaAllowHosts` (use `["*"]` to allow any host).
 
+## Sending files in group chats
+
+Bots can send files in DMs using the FileConsentCard flow (built-in). However, **sending files in group chats/channels** requires additional setup:
+
+| Context | How files are sent | Setup needed |
+|---------|-------------------|--------------|
+| **DMs** | FileConsentCard → user accepts → bot uploads | Works out of the box |
+| **Group chats/channels** | Upload to SharePoint → share link | Requires `sharePointSiteId` + Graph permissions |
+| **Images (any context)** | Base64-encoded inline | Works out of the box |
+
+### Why group chats need SharePoint
+
+Bots don't have a personal OneDrive drive (the `/me/drive` Graph API endpoint doesn't work for application identities). To send files in group chats/channels, the bot uploads to a **SharePoint site** and creates a sharing link.
+
+### Setup
+
+1. **Add Graph API permissions** in Entra ID (Azure AD) → App Registration:
+   - `Sites.ReadWrite.All` (Application) - upload files to SharePoint
+   - `Chat.Read.All` (Application) - optional, enables per-user sharing links
+
+2. **Grant admin consent** for the tenant.
+
+3. **Get your SharePoint site ID:**
+   ```bash
+   # Via Graph Explorer or curl with a valid token:
+   curl -H "Authorization: Bearer $TOKEN" \
+     "https://graph.microsoft.com/v1.0/sites/{hostname}:/{site-path}"
+
+   # Example: for a site at "contoso.sharepoint.com/sites/BotFiles"
+   curl -H "Authorization: Bearer $TOKEN" \
+     "https://graph.microsoft.com/v1.0/sites/contoso.sharepoint.com:/sites/BotFiles"
+
+   # Response includes: "id": "contoso.sharepoint.com,guid1,guid2"
+   ```
+
+4. **Configure Clawdbot:**
+   ```json5
+   {
+     channels: {
+       msteams: {
+         // ... other config ...
+         sharePointSiteId: "contoso.sharepoint.com,guid1,guid2"
+       }
+     }
+   }
+   ```
+
+### Sharing behavior
+
+| Permission | Sharing behavior |
+|------------|------------------|
+| `Sites.ReadWrite.All` only | Organization-wide sharing link (anyone in org can access) |
+| `Sites.ReadWrite.All` + `Chat.Read.All` | Per-user sharing link (only chat members can access) |
+
+Per-user sharing is more secure as only the chat participants can access the file. If `Chat.Read.All` permission is missing, the bot falls back to organization-wide sharing.
+
+### Fallback behavior
+
+| Scenario | Result |
+|----------|--------|
+| Group chat + file + `sharePointSiteId` configured | Upload to SharePoint, send sharing link |
+| Group chat + file + no `sharePointSiteId` | Attempt OneDrive upload (may fail), send text only |
+| Personal chat + file | FileConsentCard flow (works without SharePoint) |
+| Any context + image | Base64-encoded inline (works without SharePoint) |
+
+### Files stored location
+
+Uploaded files are stored in a `/ClawdbotShared/` folder in the configured SharePoint site's default document library.
+
 ## Polls (Adaptive Cards)
 Clawdbot sends Teams polls as Adaptive Cards (there is no native Teams poll API).
 
@@ -479,6 +549,82 @@ Clawdbot sends Teams polls as Adaptive Cards (there is no native Teams poll API)
 - The gateway must stay online to record votes.
 - Polls do not auto-post result summaries yet (inspect the store file if needed).
 
+## Adaptive Cards (arbitrary)
+Send any Adaptive Card JSON to Teams users or conversations using the `message` tool or CLI.
+
+The `card` parameter accepts an Adaptive Card JSON object. When `card` is provided, the message text is optional.
+
+**Agent tool:**
+```json
+{
+  "action": "send",
+  "channel": "msteams",
+  "target": "user:<id>",
+  "card": {
+    "type": "AdaptiveCard",
+    "version": "1.5",
+    "body": [{"type": "TextBlock", "text": "Hello!"}]
+  }
+}
+```
+
+**CLI:**
+```bash
+clawdbot message send --channel msteams \
+  --target "conversation:19:abc...@thread.tacv2" \
+  --card '{"type":"AdaptiveCard","version":"1.5","body":[{"type":"TextBlock","text":"Hello!"}]}'
+```
+
+See [Adaptive Cards documentation](https://adaptivecards.io/) for card schema and examples. For target format details, see [Target formats](#target-formats) below.
+
+## Target formats
+
+MSTeams targets use prefixes to distinguish between users and conversations:
+
+| Target type | Format | Example |
+|-------------|--------|---------|
+| User (by ID) | `user:<aad-object-id>` | `user:40a1a0ed-4ff2-4164-a219-55518990c197` |
+| User (by name) | `user:<display-name>` | `user:John Smith` (requires Graph API) |
+| Group/channel | `conversation:<conversation-id>` | `conversation:19:abc123...@thread.tacv2` |
+| Group/channel (raw) | `<conversation-id>` | `19:abc123...@thread.tacv2` (if contains `@thread`) |
+
+**CLI examples:**
+```bash
+# Send to a user by ID
+clawdbot message send --channel msteams --target "user:40a1a0ed-..." --message "Hello"
+
+# Send to a user by display name (triggers Graph API lookup)
+clawdbot message send --channel msteams --target "user:John Smith" --message "Hello"
+
+# Send to a group chat or channel
+clawdbot message send --channel msteams --target "conversation:19:abc...@thread.tacv2" --message "Hello"
+
+# Send an Adaptive Card to a conversation
+clawdbot message send --channel msteams --target "conversation:19:abc...@thread.tacv2" \
+  --card '{"type":"AdaptiveCard","version":"1.5","body":[{"type":"TextBlock","text":"Hello"}]}'
+```
+
+**Agent tool examples:**
+```json
+{
+  "action": "send",
+  "channel": "msteams",
+  "target": "user:John Smith",
+  "message": "Hello!"
+}
+```
+
+```json
+{
+  "action": "send",
+  "channel": "msteams",
+  "target": "conversation:19:abc...@thread.tacv2",
+  "card": {"type": "AdaptiveCard", "version": "1.5", "body": [{"type": "TextBlock", "text": "Hello"}]}
+}
+```
+
+Note: Without the `user:` prefix, names default to group/team resolution. Always use `user:` when targeting people by display name.
+
 ## Proactive messaging
 - Proactive messages are only possible **after** a user has interacted, because we store conversation references at that point.
 - See `/gateway/configuration` for `dmPolicy` and allowlist gating.

docs/channels/signal.md

@@ -100,6 +100,11 @@ Groups:
 - Use `channels.signal.ignoreAttachments` to skip downloading media.
 - Group history context uses `channels.signal.historyLimit` (or `channels.signal.accounts.*.historyLimit`), falling back to `messages.groupChat.historyLimit`. Set `0` to disable (default 50).
 
+## Typing + read receipts
+- **Typing indicators**: Clawdbot sends typing signals via `signal-cli sendTyping` and refreshes them while a reply is running.
+- **Read receipts**: when `channels.signal.sendReadReceipts` is true, Clawdbot forwards read receipts for allowed DMs.
+- Signal-cli does not expose read receipts for groups.
+
 ## Delivery targets (CLI/cron)
 - DMs: `signal:+15551234567` (or plain E.164).
 - Groups: `signal:group:<groupId>`.

docs/platforms/mac/release.md

@@ -30,17 +30,17 @@ Notes:
 # From repo root; set release IDs so Sparkle feed is enabled.
 # APP_BUILD must be numeric + monotonic for Sparkle compare.
 BUNDLE_ID=com.clawdbot.mac \
-APP_VERSION=2026.1.20 \
+APP_VERSION=2026.1.21 \
 APP_BUILD="$(git rev-list --count HEAD)" \
 BUILD_CONFIG=release \
 SIGN_IDENTITY="Developer ID Application: <Developer Name> (<TEAMID>)" \
 scripts/package-mac-app.sh
 
 # Zip for distribution (includes resource forks for Sparkle delta support)
-ditto -c -k --sequesterRsrc --keepParent dist/Clawdbot.app dist/Clawdbot-2026.1.20.zip
+ditto -c -k --sequesterRsrc --keepParent dist/Clawdbot.app dist/Clawdbot-2026.1.21.zip
 
 # Optional: also build a styled DMG for humans (drag to /Applications)
-scripts/create-dmg.sh dist/Clawdbot.app dist/Clawdbot-2026.1.20.dmg
+scripts/create-dmg.sh dist/Clawdbot.app dist/Clawdbot-2026.1.21.dmg
 
 # Recommended: build + notarize/staple zip + DMG
 # First, create a keychain profile once:
@@ -48,26 +48,26 @@ scripts/create-dmg.sh dist/Clawdbot.app dist/Clawdbot-2026.1.20.dmg
 #     --apple-id "<apple-id>" --team-id "<team-id>" --password "<app-specific-password>"
 NOTARIZE=1 NOTARYTOOL_PROFILE=clawdbot-notary \
 BUNDLE_ID=com.clawdbot.mac \
-APP_VERSION=2026.1.20 \
+APP_VERSION=2026.1.21 \
 APP_BUILD="$(git rev-list --count HEAD)" \
 BUILD_CONFIG=release \
 SIGN_IDENTITY="Developer ID Application: <Developer Name> (<TEAMID>)" \
 scripts/package-mac-dist.sh
 
 # Optional: ship dSYM alongside the release
-ditto -c -k --keepParent apps/macos/.build/release/Clawdbot.app.dSYM dist/Clawdbot-2026.1.20.dSYM.zip
+ditto -c -k --keepParent apps/macos/.build/release/Clawdbot.app.dSYM dist/Clawdbot-2026.1.21.dSYM.zip
 ```
 
 ## Appcast entry
 Use the release note generator so Sparkle renders formatted HTML notes:
 ```bash
-SPARKLE_PRIVATE_KEY_FILE=/path/to/ed25519-private-key scripts/make_appcast.sh dist/Clawdbot-2026.1.20.zip https://raw.githubusercontent.com/clawdbot/clawdbot/main/appcast.xml
+SPARKLE_PRIVATE_KEY_FILE=/path/to/ed25519-private-key scripts/make_appcast.sh dist/Clawdbot-2026.1.21.zip https://raw.githubusercontent.com/clawdbot/clawdbot/main/appcast.xml
 ```
 Generates HTML release notes from `CHANGELOG.md` (via [`scripts/changelog-to-html.sh`](https://github.com/clawdbot/clawdbot/blob/main/scripts/changelog-to-html.sh)) and embeds them in the appcast entry.
 Commit the updated `appcast.xml` alongside the release assets (zip + dSYM) when publishing.
 
 ## Publish & verify
-- Upload `Clawdbot-2026.1.20.zip` (and `Clawdbot-2026.1.20.dSYM.zip`) to the GitHub release for tag `v2026.1.20`.
+- Upload `Clawdbot-2026.1.21.zip` (and `Clawdbot-2026.1.21.dSYM.zip`) to the GitHub release for tag `v2026.1.21`.
 - Ensure the raw appcast URL matches the baked feed: `https://raw.githubusercontent.com/clawdbot/clawdbot/main/appcast.xml`.
 - Sanity checks:
   - `curl -I https://raw.githubusercontent.com/clawdbot/clawdbot/main/appcast.xml` returns 200.

docs/tools/index.md

@@ -154,6 +154,9 @@ See [Plugins](/plugin) for install + config, and [Skills](/tools/skills) for how
 tool usage guidance is injected into prompts. Some plugins ship their own skills
 alongside tools (for example, the voice-call plugin).
 
+Optional plugin tools:
+- [Lobster](/tools/lobster): typed workflow runtime with resumable approvals (requires the Lobster CLI on the gateway host).
+
 ## Tool inventory
 
 ### `apply_patch`
@@ -319,7 +322,7 @@ Notes:
 Send messages and channel actions across Discord/Slack/Telegram/WhatsApp/Signal/iMessage/MS Teams.
 
 Core actions:
-- `send` (text + optional media)
+- `send` (text + optional media; MS Teams also supports `card` for Adaptive Cards)
 - `poll` (WhatsApp/Discord/MS Teams polls)
 - `react` / `reactions` / `read` / `edit` / `delete`
 - `pin` / `unpin` / `list-pins`

docs/tools/lobster.md

@@ -0,0 +1,171 @@
+---
+title: Lobster
+summary: "Typed workflow runtime for Clawdbot with resumable approval gates."
+description: Typed workflow runtime for Clawdbot — composable pipelines with approval gates.
+read_when:
+  - You want deterministic multi-step workflows with explicit approvals
+  - You need to resume a workflow without re-running earlier steps
+---
+
+# Lobster
+
+Lobster is a workflow shell that lets Clawdbot run multi-step tool sequences as a single, deterministic operation with explicit approval checkpoints.
+
+## Why
+
+Today, complex workflows require many back-and-forth tool calls. Each call costs tokens, and the LLM has to orchestrate every step. Lobster moves that orchestration into a typed runtime:
+
+- **One call instead of many**: Clawdbot runs one Lobster tool call and gets a structured result.
+- **Approvals built in**: Side effects (send email, post comment) halt the workflow until explicitly approved.
+- **Resumable**: Halted workflows return a token; approve and resume without re-running everything.
+
+## How it works
+
+Clawdbot launches the local `lobster` CLI in **tool mode** and parses a JSON envelope from stdout.
+If the pipeline pauses for approval, the tool returns a `resumeToken` so you can continue later.
+
+## Install Lobster
+
+Install the Lobster CLI on the **same host** that runs the Clawdbot Gateway (see the [Lobster repo](https://github.com/vignesh07/lobster)), and ensure `lobster` is on `PATH`.
+If you want to use a custom binary location, pass an **absolute** `lobsterPath` in the tool call.
+
+## Enable the tool
+
+Lobster is an **optional** plugin tool (not enabled by default). Allow it per agent:
+
+```json
+{
+  "agents": {
+    "list": [
+      {
+        "id": "main",
+        "tools": {
+          "allow": ["lobster"]
+        }
+      }
+    ]
+  }
+}
+```
+
+You can also allow it globally with `tools.allow` if every agent should see it.
+
+## Example: Email triage
+
+Without Lobster:
+```
+User: "Check my email and draft replies"
+→ clawd calls gmail.list
+→ LLM summarizes
+→ User: "draft replies to #2 and #5"
+→ LLM drafts
+→ User: "send #2"
+→ clawd calls gmail.send
+(repeat daily, no memory of what was triaged)
+```
+
+With Lobster:
+```json
+{
+  "action": "run",
+  "pipeline": "email.triage --limit 20",
+  "timeoutMs": 30000
+}
+```
+
+Returns a JSON envelope (truncated):
+```json
+{
+  "ok": true,
+  "status": "needs_approval",
+  "output": [{ "summary": "5 need replies, 2 need action" }],
+  "requiresApproval": {
+    "type": "approval_request",
+    "prompt": "Send 2 draft replies?",
+    "items": [],
+    "resumeToken": "..."
+  }
+}
+```
+
+User approves → resume:
+```json
+{
+  "action": "resume",
+  "token": "<resumeToken>",
+  "approve": true
+}
+```
+
+One workflow. Deterministic. Safe.
+
+## Tool parameters
+
+### `run`
+
+Run a pipeline in tool mode.
+
+```json
+{
+  "action": "run",
+  "pipeline": "gog.gmail.search --query 'newer_than:1d' | email.triage",
+  "cwd": "/path/to/workspace",
+  "timeoutMs": 30000,
+  "maxStdoutBytes": 512000
+}
+```
+
+### `resume`
+
+Continue a halted workflow after approval.
+
+```json
+{
+  "action": "resume",
+  "token": "<resumeToken>",
+  "approve": true
+}
+```
+
+### Optional inputs
+
+- `lobsterPath`: Absolute path to the Lobster binary (omit to use `PATH`).
+- `cwd`: Working directory for the pipeline (defaults to the current process working directory).
+- `timeoutMs`: Kill the subprocess if it exceeds this duration (default: 20000).
+- `maxStdoutBytes`: Kill the subprocess if stdout exceeds this size (default: 512000).
+
+## Output envelope
+
+Lobster returns a JSON envelope with one of three statuses:
+
+- `ok` → finished successfully
+- `needs_approval` → paused; `requiresApproval.resumeToken` is required to resume
+- `cancelled` → explicitly denied or cancelled
+
+The tool surfaces the envelope in both `content` (pretty JSON) and `details` (raw object).
+
+## Approvals
+
+If `requiresApproval` is present, inspect the prompt and decide:
+
+- `approve: true` → resume and continue side effects
+- `approve: false` → cancel and finalize the workflow
+
+## Safety
+
+- **Local subprocess only** — no network calls from the plugin itself.
+- **No secrets** — Lobster doesn't manage OAuth; it calls clawd tools that do.
+- **Sandbox-aware** — disabled when the tool context is sandboxed.
+- **Hardened** — `lobsterPath` must be absolute if specified; timeouts and output caps enforced.
+
+## Troubleshooting
+
+- **`lobster subprocess timed out`** → increase `timeoutMs`, or split a long pipeline.
+- **`lobster output exceeded maxStdoutBytes`** → raise `maxStdoutBytes` or reduce output size.
+- **`lobster returned invalid JSON`** → ensure the pipeline runs in tool mode and prints only JSON.
+- **`lobster failed (code …)`** → run the same pipeline in a terminal to inspect stderr.
+
+## Learn more
+
+- [Plugins](/plugin)
+- [Plugin tool authoring](/plugins/agent-tools)

extensions/bluebubbles/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/bluebubbles",
-  "version": "2026.1.21-1",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot BlueBubbles channel plugin",
   "clawdbot": {

extensions/copilot-proxy/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/copilot-proxy",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot Copilot Proxy provider plugin",
   "clawdbot": {

extensions/diagnostics-otel/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/diagnostics-otel",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot diagnostics OpenTelemetry exporter",
   "clawdbot": {
@@ -10,15 +10,15 @@
   },
   "dependencies": {
     "@opentelemetry/api": "^1.9.0",
-    "@opentelemetry/api-logs": "^0.210.0",
-    "@opentelemetry/exporter-logs-otlp-http": "^0.210.0",
-    "@opentelemetry/exporter-metrics-otlp-http": "^0.210.0",
-    "@opentelemetry/exporter-trace-otlp-http": "^0.210.0",
-    "@opentelemetry/resources": "^2.4.0",
-    "@opentelemetry/sdk-logs": "^0.210.0",
-    "@opentelemetry/sdk-metrics": "^2.4.0",
-    "@opentelemetry/sdk-node": "^0.210.0",
-    "@opentelemetry/sdk-trace-base": "^2.4.0",
+    "@opentelemetry/api-logs": "^0.211.0",
+    "@opentelemetry/exporter-logs-otlp-http": "^0.211.0",
+    "@opentelemetry/exporter-metrics-otlp-http": "^0.211.0",
+    "@opentelemetry/exporter-trace-otlp-http": "^0.211.0",
+    "@opentelemetry/resources": "^2.5.0",
+    "@opentelemetry/sdk-logs": "^0.211.0",
+    "@opentelemetry/sdk-metrics": "^2.5.0",
+    "@opentelemetry/sdk-node": "^0.211.0",
+    "@opentelemetry/sdk-trace-base": "^2.5.0",
     "@opentelemetry/semantic-conventions": "^1.39.0"
   }
 }

extensions/discord/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/discord",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot Discord channel plugin",
   "clawdbot": {

extensions/google-antigravity-auth/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/google-antigravity-auth",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot Google Antigravity OAuth provider plugin",
   "clawdbot": {

extensions/google-gemini-cli-auth/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/google-gemini-cli-auth",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot Gemini CLI OAuth provider plugin",
   "clawdbot": {

extensions/imessage/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/imessage",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot iMessage channel plugin",
   "clawdbot": {

extensions/lobster/README.md

@@ -0,0 +1,38 @@
+# Lobster (plugin)
+
+Adds the `lobster` agent tool as an **optional** plugin tool.
+
+## What this is
+
+- Lobster is a standalone workflow shell (typed JSON-first pipelines + approvals/resume).
+- This plugin integrates Lobster with Clawdbot *without core changes*.
+
+## Enable
+
+Because this tool can trigger side effects (via workflows), it is registered with `optional: true`.
+
+Enable it in an agent allowlist:
+
+```json
+{
+  "agents": {
+    "list": [
+      {
+        "id": "main",
+        "tools": {
+          "allow": [
+            "lobster" // plugin id (enables all tools from this plugin)
+          ]
+        }
+      }
+    ]
+  }
+}
+```
+
+## Security
+
+- Runs the `lobster` executable as a local subprocess.
+- Does not manage OAuth/tokens.
+- Uses timeouts, stdout caps, and strict JSON envelope parsing.
+- Prefer an absolute `lobsterPath` in production to avoid PATH hijack.

extensions/lobster/SKILL.md

@@ -0,0 +1,90 @@
+# Lobster
+
+Lobster executes multi-step workflows with approval checkpoints. Use it when:
+
+- User wants a repeatable automation (triage, monitor, sync)
+- Actions need human approval before executing (send, post, delete)
+- Multiple tool calls should run as one deterministic operation
+
+## When to use Lobster
+
+| User intent | Use Lobster? |
+|-------------|--------------|
+| "Triage my email" | Yes — multi-step, may send replies |
+| "Send a message" | No — single action, use message tool directly |
+| "Check my email every morning and ask before replying" | Yes — scheduled workflow with approval |
+| "What's the weather?" | No — simple query |
+| "Monitor this PR and notify me of changes" | Yes — stateful, recurring |
+
+## Basic usage
+
+### Run a pipeline
+
+```json
+{
+  "action": "run",
+  "pipeline": "gog.gmail.search --query 'newer_than:1d' --max 20 | email.triage"
+}
+```
+
+Returns structured result:
+```json
+{
+  "protocolVersion": 1,
+  "ok": true,
+  "status": "ok",
+  "output": [{ "summary": {...}, "items": [...] }],
+  "requiresApproval": null
+}
+```
+
+### Handle approval
+
+If the workflow needs approval:
+```json
+{
+  "status": "needs_approval",
+  "output": [],
+  "requiresApproval": {
+    "prompt": "Send 3 draft replies?",
+    "items": [...],
+    "resumeToken": "..."
+  }
+}
+```
+
+Present the prompt to the user. If they approve:
+```json
+{
+  "action": "resume",
+  "token": "<resumeToken>",
+  "approve": true
+}
+```
+
+## Example workflows
+
+### Email triage
+```
+gog.gmail.search --query 'newer_than:1d' --max 20 | email.triage
+```
+Fetches recent emails, classifies into buckets (needs_reply, needs_action, fyi).
+
+### Email triage with approval gate
+```
+gog.gmail.search --query 'newer_than:1d' | email.triage | approve --prompt 'Process these?'
+```
+Same as above, but halts for approval before returning.
+
+## Key behaviors
+
+- **Deterministic**: Same input → same output (no LLM variance in pipeline execution)
+- **Approval gates**: `approve` command halts execution, returns token
+- **Resumable**: Use `resume` action with token to continue
+- **Structured output**: Always returns JSON envelope with `protocolVersion`
+
+## Don't use Lobster for
+
+- Simple single-action requests (just use the tool directly)
+- Queries that need LLM interpretation mid-flow
+- One-off tasks that won't be repeated

extensions/lobster/clawdbot.plugin.json

@@ -0,0 +1,10 @@
+{
+  "id": "lobster",
+  "name": "Lobster",
+  "description": "Typed workflow tool with resumable approvals.",
+  "configSchema": {
+    "type": "object",
+    "additionalProperties": false,
+    "properties": {}
+  }
+}

extensions/lobster/index.ts

@@ -0,0 +1,13 @@
+import type { ClawdbotPluginApi } from "../../src/plugins/types.js";
+
+import { createLobsterTool } from "./src/lobster-tool.js";
+
+export default function register(api: ClawdbotPluginApi) {
+  api.registerTool(
+    (ctx) => {
+      if (ctx.sandboxed) return null;
+      return createLobsterTool(api);
+    },
+    { optional: true },
+  );
+}

extensions/lobster/package.json

@@ -0,0 +1,9 @@
+{
+  "name": "@clawdbot/lobster",
+  "version": "2026.1.17-1",
+  "type": "module",
+  "description": "Lobster workflow tool plugin (typed pipelines + resumable approvals)",
+  "clawdbot": {
+    "extensions": ["./index.ts"]
+  }
+}

extensions/lobster/src/lobster-tool.test.ts

@@ -0,0 +1,123 @@
+import fs from "node:fs/promises";
+import os from "node:os";
+import path from "node:path";
+
+import { describe, expect, it } from "vitest";
+
+import type { ClawdbotPluginApi, ClawdbotPluginToolContext } from "../../../src/plugins/types.js";
+import { createLobsterTool } from "./lobster-tool.js";
+
+async function writeFakeLobsterScript(scriptBody: string, prefix = "clawdbot-lobster-plugin-") {
+  const dir = await fs.mkdtemp(path.join(os.tmpdir(), prefix));
+  const isWindows = process.platform === "win32";
+
+  if (isWindows) {
+    const scriptPath = path.join(dir, "lobster.js");
+    const cmdPath = path.join(dir, "lobster.cmd");
+    await fs.writeFile(scriptPath, scriptBody, { encoding: "utf8" });
+    const cmd = `@echo off\r\n"${process.execPath}" "${scriptPath}" %*\r\n`;
+    await fs.writeFile(cmdPath, cmd, { encoding: "utf8" });
+    return { dir, binPath: cmdPath };
+  }
+
+  const binPath = path.join(dir, "lobster");
+  const file = `#!/usr/bin/env node\n${scriptBody}\n`;
+  await fs.writeFile(binPath, file, { encoding: "utf8", mode: 0o755 });
+  return { dir, binPath };
+}
+
+async function writeFakeLobster(params: { payload: unknown }) {
+  const scriptBody =
+    `const payload = ${JSON.stringify(params.payload)};\n` +
+    `process.stdout.write(JSON.stringify(payload));\n`;
+  return await writeFakeLobsterScript(scriptBody);
+}
+
+function fakeApi(): ClawdbotPluginApi {
+  return {
+    id: "lobster",
+    name: "lobster",
+    source: "test",
+    config: {} as any,
+    runtime: { version: "test" } as any,
+    logger: { info() {}, warn() {}, error() {}, debug() {} },
+    registerTool() {},
+    registerHttpHandler() {},
+    registerChannel() {},
+    registerGatewayMethod() {},
+    registerCli() {},
+    registerService() {},
+    registerProvider() {},
+    resolvePath: (p) => p,
+  };
+}
+
+function fakeCtx(overrides: Partial<ClawdbotPluginToolContext> = {}): ClawdbotPluginToolContext {
+  return {
+    config: {} as any,
+    workspaceDir: "/tmp",
+    agentDir: "/tmp",
+    agentId: "main",
+    sessionKey: "main",
+    messageChannel: undefined,
+    agentAccountId: undefined,
+    sandboxed: false,
+    ...overrides,
+  };
+}
+
+describe("lobster plugin tool", () => {
+  it("runs lobster and returns parsed envelope in details", async () => {
+    const fake = await writeFakeLobster({
+      payload: { ok: true, status: "ok", output: [{ hello: "world" }], requiresApproval: null },
+    });
+
+    const tool = createLobsterTool(fakeApi());
+    const res = await tool.execute("call1", {
+      action: "run",
+      pipeline: "noop",
+      lobsterPath: fake.binPath,
+      timeoutMs: 1000,
+    });
+
+    expect(res.details).toMatchObject({ ok: true, status: "ok" });
+  });
+
+  it("requires absolute lobsterPath when provided", async () => {
+    const tool = createLobsterTool(fakeApi());
+    await expect(
+      tool.execute("call2", {
+        action: "run",
+        pipeline: "noop",
+        lobsterPath: "./lobster",
+      }),
+    ).rejects.toThrow(/absolute path/);
+  });
+
+  it("rejects invalid JSON from lobster", async () => {
+    const { binPath } = await writeFakeLobsterScript(
+      `process.stdout.write("nope");\n`,
+      "clawdbot-lobster-plugin-bad-",
+    );
+
+    const tool = createLobsterTool(fakeApi());
+    await expect(
+      tool.execute("call3", {
+        action: "run",
+        pipeline: "noop",
+        lobsterPath: binPath,
+      }),
+    ).rejects.toThrow(/invalid JSON/);
+  });
+
+  it("can be gated off in sandboxed contexts", async () => {
+    const api = fakeApi();
+    const factoryTool = (ctx: ClawdbotPluginToolContext) => {
+      if (ctx.sandboxed) return null;
+      return createLobsterTool(api);
+    };
+
+    expect(factoryTool(fakeCtx({ sandboxed: true }))).toBeNull();
+    expect(factoryTool(fakeCtx({ sandboxed: false }))?.name).toBe("lobster");
+  });
+});

extensions/lobster/src/lobster-tool.ts

@@ -0,0 +1,188 @@
+import { Type } from "@sinclair/typebox";
+import { spawn } from "node:child_process";
+import path from "node:path";
+
+import type { ClawdbotPluginApi } from "../../../src/plugins/types.js";
+
+type LobsterEnvelope =
+  | {
+      ok: true;
+      status: "ok" | "needs_approval" | "cancelled";
+      output: unknown[];
+      requiresApproval: null | {
+        type: "approval_request";
+        prompt: string;
+        items: unknown[];
+        resumeToken?: string;
+      };
+    }
+  | {
+      ok: false;
+      error: { type?: string; message: string };
+    };
+
+function resolveExecutablePath(lobsterPathRaw: string | undefined) {
+  const lobsterPath = lobsterPathRaw?.trim() || "lobster";
+  if (lobsterPath !== "lobster" && !path.isAbsolute(lobsterPath)) {
+    throw new Error("lobsterPath must be an absolute path (or omit to use PATH)");
+  }
+  return lobsterPath;
+}
+
+async function runLobsterSubprocess(params: {
+  execPath: string;
+  argv: string[];
+  cwd: string;
+  timeoutMs: number;
+  maxStdoutBytes: number;
+}) {
+  const { execPath, argv, cwd } = params;
+  const timeoutMs = Math.max(200, params.timeoutMs);
+  const maxStdoutBytes = Math.max(1024, params.maxStdoutBytes);
+
+  const env = { ...process.env, LOBSTER_MODE: "tool" } as Record<string, string | undefined>;
+  const nodeOptions = env.NODE_OPTIONS ?? "";
+  if (nodeOptions.includes("--inspect")) {
+    delete env.NODE_OPTIONS;
+  }
+
+  return await new Promise<{ stdout: string }>((resolve, reject) => {
+    const child = spawn(execPath, argv, {
+      cwd,
+      stdio: ["ignore", "pipe", "pipe"],
+      env,
+    });
+
+    let stdout = "";
+    let stdoutBytes = 0;
+    let stderr = "";
+
+    child.stdout?.setEncoding("utf8");
+    child.stderr?.setEncoding("utf8");
+
+    child.stdout?.on("data", (chunk) => {
+      const str = String(chunk);
+      stdoutBytes += Buffer.byteLength(str, "utf8");
+      if (stdoutBytes > maxStdoutBytes) {
+        try {
+          child.kill("SIGKILL");
+        } finally {
+          reject(new Error("lobster output exceeded maxStdoutBytes"));
+        }
+        return;
+      }
+      stdout += str;
+    });
+
+    child.stderr?.on("data", (chunk) => {
+      stderr += String(chunk);
+    });
+
+    const timer = setTimeout(() => {
+      try {
+        child.kill("SIGKILL");
+      } finally {
+        reject(new Error("lobster subprocess timed out"));
+      }
+    }, timeoutMs);
+
+    child.once("error", (err) => {
+      clearTimeout(timer);
+      reject(err);
+    });
+
+    child.once("exit", (code) => {
+      clearTimeout(timer);
+      if (code !== 0) {
+        reject(new Error(`lobster failed (${code ?? "?"}): ${stderr.trim() || stdout.trim()}`));
+        return;
+      }
+      resolve({ stdout });
+    });
+  });
+}
+
+function parseEnvelope(stdout: string): LobsterEnvelope {
+  let parsed: unknown;
+  try {
+    parsed = JSON.parse(stdout);
+  } catch {
+    throw new Error("lobster returned invalid JSON");
+  }
+
+  if (!parsed || typeof parsed !== "object") {
+    throw new Error("lobster returned invalid JSON envelope");
+  }
+
+  const ok = (parsed as { ok?: unknown }).ok;
+  if (ok === true || ok === false) {
+    return parsed as LobsterEnvelope;
+  }
+
+  throw new Error("lobster returned invalid JSON envelope");
+}
+
+export function createLobsterTool(api: ClawdbotPluginApi) {
+  return {
+    name: "lobster",
+    description:
+      "Run Lobster pipelines as a local-first workflow runtime (typed JSON envelope + resumable approvals).",
+    parameters: Type.Object({
+      // NOTE: Prefer string enums in tool schemas; some providers reject unions/anyOf.
+      action: Type.Unsafe<"run" | "resume">({ type: "string", enum: ["run", "resume"] }),
+      pipeline: Type.Optional(Type.String()),
+      token: Type.Optional(Type.String()),
+      approve: Type.Optional(Type.Boolean()),
+      lobsterPath: Type.Optional(Type.String()),
+      cwd: Type.Optional(Type.String()),
+      timeoutMs: Type.Optional(Type.Number()),
+      maxStdoutBytes: Type.Optional(Type.Number()),
+    }),
+    async execute(_id: string, params: Record<string, unknown>) {
+      const action = String(params.action || "").trim();
+      if (!action) throw new Error("action required");
+
+      const execPath = resolveExecutablePath(
+        typeof params.lobsterPath === "string" ? params.lobsterPath : undefined,
+      );
+      const cwd = typeof params.cwd === "string" && params.cwd.trim() ? params.cwd.trim() : process.cwd();
+      const timeoutMs = typeof params.timeoutMs === "number" ? params.timeoutMs : 20_000;
+      const maxStdoutBytes = typeof params.maxStdoutBytes === "number" ? params.maxStdoutBytes : 512_000;
+
+      const argv = (() => {
+        if (action === "run") {
+          const pipeline = typeof params.pipeline === "string" ? params.pipeline : "";
+          if (!pipeline.trim()) throw new Error("pipeline required");
+          return ["run", "--mode", "tool", pipeline];
+        }
+        if (action === "resume") {
+          const token = typeof params.token === "string" ? params.token : "";
+          if (!token.trim()) throw new Error("token required");
+          const approve = params.approve;
+          if (typeof approve !== "boolean") throw new Error("approve required");
+          return ["resume", "--token", token, "--approve", approve ? "yes" : "no"];
+        }
+        throw new Error(`Unknown action: ${action}`);
+      })();
+
+      if (api.runtime?.version && api.logger?.debug) {
+        api.logger.debug(`lobster plugin runtime=${api.runtime.version}`);
+      }
+
+      const { stdout } = await runLobsterSubprocess({
+        execPath,
+        argv,
+        cwd,
+        timeoutMs,
+        maxStdoutBytes,
+      });
+
+      const envelope = parseEnvelope(stdout);
+
+      return {
+        content: [{ type: "text", text: JSON.stringify(envelope, null, 2) }],
+        details: envelope,
+      };
+    },
+  };
+}

extensions/matrix/CHANGELOG.md

@@ -1,6 +1,6 @@
 # Changelog
 
-## 2026.1.20-2
+## 2026.1.21
 
 ### Changes
 - Version alignment with core Clawdbot release numbers.

extensions/matrix/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/matrix",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot Matrix channel plugin",
   "clawdbot": {

extensions/memory-core/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/memory-core",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot core memory search plugin",
   "clawdbot": {

extensions/memory-lancedb/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/memory-lancedb",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot LanceDB-backed long-term memory plugin with auto-recall/capture",
   "dependencies": {

extensions/msteams/CHANGELOG.md

@@ -1,6 +1,6 @@
 # Changelog
 
-## 2026.1.20-2
+## 2026.1.21
 
 ### Changes
 - Version alignment with core Clawdbot release numbers.

extensions/msteams/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/msteams",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot Microsoft Teams channel plugin",
   "clawdbot": {

extensions/msteams/src/attachments.test.ts

@@ -101,9 +101,9 @@ describe("msteams attachments", () => {
     });
   });
 
-  describe("downloadMSTeamsImageAttachments", () => {
+  describe("downloadMSTeamsAttachments", () => {
     it("downloads and stores image contentUrl attachments", async () => {
-      const { downloadMSTeamsImageAttachments } = await load();
+      const { downloadMSTeamsAttachments } = await load();
       const fetchMock = vi.fn(async () => {
         return new Response(Buffer.from("png"), {
           status: 200,
@@ -111,7 +111,7 @@ describe("msteams attachments", () => {
         });
       });
 
-      const media = await downloadMSTeamsImageAttachments({
+      const media = await downloadMSTeamsAttachments({
         attachments: [{ contentType: "image/png", contentUrl: "https://x/img" }],
         maxBytes: 1024 * 1024,
         allowHosts: ["x"],
@@ -125,7 +125,7 @@ describe("msteams attachments", () => {
     });
 
     it("supports Teams file.download.info downloadUrl attachments", async () => {
-      const { downloadMSTeamsImageAttachments } = await load();
+      const { downloadMSTeamsAttachments } = await load();
       const fetchMock = vi.fn(async () => {
         return new Response(Buffer.from("png"), {
           status: 200,
@@ -133,7 +133,7 @@ describe("msteams attachments", () => {
         });
       });
 
-      const media = await downloadMSTeamsImageAttachments({
+      const media = await downloadMSTeamsAttachments({
         attachments: [
           {
             contentType: "application/vnd.microsoft.teams.file.download.info",
@@ -149,8 +149,35 @@ describe("msteams attachments", () => {
       expect(media).toHaveLength(1);
     });
 
+    it("downloads non-image file attachments (PDF)", async () => {
+      const { downloadMSTeamsAttachments } = await load();
+      const fetchMock = vi.fn(async () => {
+        return new Response(Buffer.from("pdf"), {
+          status: 200,
+          headers: { "content-type": "application/pdf" },
+        });
+      });
+      detectMimeMock.mockResolvedValueOnce("application/pdf");
+      saveMediaBufferMock.mockResolvedValueOnce({
+        path: "/tmp/saved.pdf",
+        contentType: "application/pdf",
+      });
+
+      const media = await downloadMSTeamsAttachments({
+        attachments: [{ contentType: "application/pdf", contentUrl: "https://x/doc.pdf" }],
+        maxBytes: 1024 * 1024,
+        allowHosts: ["x"],
+        fetchFn: fetchMock as unknown as typeof fetch,
+      });
+
+      expect(fetchMock).toHaveBeenCalledWith("https://x/doc.pdf");
+      expect(media).toHaveLength(1);
+      expect(media[0]?.path).toBe("/tmp/saved.pdf");
+      expect(media[0]?.placeholder).toBe("<media:document>");
+    });
+
     it("downloads inline image URLs from html attachments", async () => {
-      const { downloadMSTeamsImageAttachments } = await load();
+      const { downloadMSTeamsAttachments } = await load();
       const fetchMock = vi.fn(async () => {
         return new Response(Buffer.from("png"), {
           status: 200,
@@ -158,7 +185,7 @@ describe("msteams attachments", () => {
         });
       });
 
-      const media = await downloadMSTeamsImageAttachments({
+      const media = await downloadMSTeamsAttachments({
         attachments: [
           {
             contentType: "text/html",
@@ -175,9 +202,9 @@ describe("msteams attachments", () => {
     });
 
     it("stores inline data:image base64 payloads", async () => {
-      const { downloadMSTeamsImageAttachments } = await load();
+      const { downloadMSTeamsAttachments } = await load();
       const base64 = Buffer.from("png").toString("base64");
-      const media = await downloadMSTeamsImageAttachments({
+      const media = await downloadMSTeamsAttachments({
         attachments: [
           {
             contentType: "text/html",
@@ -193,7 +220,7 @@ describe("msteams attachments", () => {
     });
 
     it("retries with auth when the first request is unauthorized", async () => {
-      const { downloadMSTeamsImageAttachments } = await load();
+      const { downloadMSTeamsAttachments } = await load();
       const fetchMock = vi.fn(async (_url: string, opts?: RequestInit) => {
         const hasAuth = Boolean(
           opts &&
@@ -210,7 +237,7 @@ describe("msteams attachments", () => {
         });
       });
 
-      const media = await downloadMSTeamsImageAttachments({
+      const media = await downloadMSTeamsAttachments({
         attachments: [{ contentType: "image/png", contentUrl: "https://x/img" }],
         maxBytes: 1024 * 1024,
         tokenProvider: { getAccessToken: vi.fn(async () => "token") },
@@ -224,9 +251,9 @@ describe("msteams attachments", () => {
     });
 
     it("skips urls outside the allowlist", async () => {
-      const { downloadMSTeamsImageAttachments } = await load();
+      const { downloadMSTeamsAttachments } = await load();
       const fetchMock = vi.fn();
-      const media = await downloadMSTeamsImageAttachments({
+      const media = await downloadMSTeamsAttachments({
         attachments: [{ contentType: "image/png", contentUrl: "https://evil.test/img" }],
         maxBytes: 1024 * 1024,
         allowHosts: ["graph.microsoft.com"],
@@ -236,20 +263,6 @@ describe("msteams attachments", () => {
       expect(media).toHaveLength(0);
       expect(fetchMock).not.toHaveBeenCalled();
     });
-
-    it("ignores non-image attachments", async () => {
-      const { downloadMSTeamsImageAttachments } = await load();
-      const fetchMock = vi.fn();
-      const media = await downloadMSTeamsImageAttachments({
-        attachments: [{ contentType: "application/pdf", contentUrl: "https://x/x.pdf" }],
-        maxBytes: 1024 * 1024,
-        allowHosts: ["x"],
-        fetchFn: fetchMock as unknown as typeof fetch,
-      });
-
-      expect(media).toHaveLength(0);
-      expect(fetchMock).not.toHaveBeenCalled();
-    });
   });
 
   describe("buildMSTeamsGraphMessageUrls", () => {
@@ -324,6 +337,74 @@ describe("msteams attachments", () => {
       expect(fetchMock).toHaveBeenCalled();
       expect(saveMediaBufferMock).toHaveBeenCalled();
     });
+
+    it("merges SharePoint reference attachments with hosted content", async () => {
+      const { downloadMSTeamsGraphMedia } = await load();
+      const hostedBase64 = Buffer.from("png").toString("base64");
+      const shareUrl = "https://contoso.sharepoint.com/site/file";
+      const fetchMock = vi.fn(async (url: string) => {
+        if (url.endsWith("/hostedContents")) {
+          return new Response(
+            JSON.stringify({
+              value: [
+                {
+                  id: "hosted-1",
+                  contentType: "image/png",
+                  contentBytes: hostedBase64,
+                },
+              ],
+            }),
+            { status: 200 },
+          );
+        }
+        if (url.endsWith("/attachments")) {
+          return new Response(
+            JSON.stringify({
+              value: [
+                {
+                  id: "ref-1",
+                  contentType: "reference",
+                  contentUrl: shareUrl,
+                  name: "report.pdf",
+                },
+              ],
+            }),
+            { status: 200 },
+          );
+        }
+        if (url.startsWith("https://graph.microsoft.com/v1.0/shares/")) {
+          return new Response(Buffer.from("pdf"), {
+            status: 200,
+            headers: { "content-type": "application/pdf" },
+          });
+        }
+        if (url.endsWith("/messages/123")) {
+          return new Response(
+            JSON.stringify({
+              attachments: [
+                {
+                  id: "ref-1",
+                  contentType: "reference",
+                  contentUrl: shareUrl,
+                  name: "report.pdf",
+                },
+              ],
+            }),
+            { status: 200 },
+          );
+        }
+        return new Response("not found", { status: 404 });
+      });
+
+      const media = await downloadMSTeamsGraphMedia({
+        messageUrl: "https://graph.microsoft.com/v1.0/chats/19%3Achat/messages/123",
+        tokenProvider: { getAccessToken: vi.fn(async () => "token") },
+        maxBytes: 1024 * 1024,
+        fetchFn: fetchMock as unknown as typeof fetch,
+      });
+
+      expect(media.media).toHaveLength(2);
+    });
   });
 
   describe("buildMSTeamsMediaPayload", () => {

extensions/msteams/src/attachments.ts

@@ -1,4 +1,8 @@
-export { downloadMSTeamsImageAttachments } from "./attachments/download.js";
+export {
+  downloadMSTeamsAttachments,
+  /** @deprecated Use `downloadMSTeamsAttachments` instead. */
+  downloadMSTeamsImageAttachments,
+} from "./attachments/download.js";
 export { buildMSTeamsGraphMessageUrls, downloadMSTeamsGraphMedia } from "./attachments/graph.js";
 export {
   buildMSTeamsAttachmentPlaceholder,

extensions/msteams/src/attachments/download.ts

@@ -2,7 +2,7 @@ import { getMSTeamsRuntime } from "../runtime.js";
 import {
   extractInlineImageCandidates,
   inferPlaceholder,
-  isLikelyImageAttachment,
+  isDownloadableAttachment,
   isRecord,
   isUrlAllowed,
   normalizeContentType,
@@ -102,23 +102,31 @@ async function fetchWithAuthFallback(params: {
   return firstAttempt;
 }
 
-export async function downloadMSTeamsImageAttachments(params: {
+/**
+ * Download all file attachments from a Teams message (images, documents, etc.).
+ * Renamed from downloadMSTeamsImageAttachments to support all file types.
+ */
+export async function downloadMSTeamsAttachments(params: {
   attachments: MSTeamsAttachmentLike[] | undefined;
   maxBytes: number;
   tokenProvider?: MSTeamsAccessTokenProvider;
   allowHosts?: string[];
   fetchFn?: typeof fetch;
+  /** When true, embeds original filename in stored path for later extraction. */
+  preserveFilenames?: boolean;
 }): Promise<MSTeamsInboundMedia[]> {
   const list = Array.isArray(params.attachments) ? params.attachments : [];
   if (list.length === 0) return [];
   const allowHosts = resolveAllowedHosts(params.allowHosts);
 
-  const candidates: DownloadCandidate[] = list
-    .filter(isLikelyImageAttachment)
+  // Download ANY downloadable attachment (not just images)
+  const downloadable = list.filter(isDownloadableAttachment);
+  const candidates: DownloadCandidate[] = downloadable
     .map(resolveDownloadCandidate)
     .filter(Boolean) as DownloadCandidate[];
 
   const inlineCandidates = extractInlineImageCandidates(list);
+
   const seenUrls = new Set<string>();
   for (const inline of inlineCandidates) {
     if (inline.kind === "url") {
@@ -133,7 +141,6 @@ export async function downloadMSTeamsImageAttachments(params: {
       });
     }
   }
-
   if (candidates.length === 0 && inlineCandidates.length === 0) return [];
 
   const out: MSTeamsInboundMedia[] = [];
@@ -141,6 +148,7 @@ export async function downloadMSTeamsImageAttachments(params: {
     if (inline.kind !== "data") continue;
     if (inline.data.byteLength > params.maxBytes) continue;
     try {
+      // Data inline candidates (base64 data URLs) don't have original filenames
       const saved = await getMSTeamsRuntime().channel.media.saveMediaBuffer(
         inline.data,
         inline.contentType,
@@ -172,11 +180,13 @@ export async function downloadMSTeamsImageAttachments(params: {
         headerMime: res.headers.get("content-type"),
         filePath: candidate.fileHint ?? candidate.url,
       });
+      const originalFilename = params.preserveFilenames ? candidate.fileHint : undefined;
       const saved = await getMSTeamsRuntime().channel.media.saveMediaBuffer(
         buffer,
         mime ?? candidate.contentTypeHint,
         "inbound",
         params.maxBytes,
+        originalFilename,
       );
       out.push({
         path: saved.path,
@@ -184,8 +194,13 @@ export async function downloadMSTeamsImageAttachments(params: {
         placeholder: candidate.placeholder,
       });
     } catch {
-      // Ignore download failures and continue.
+      // Ignore download failures and continue with next candidate.
     }
   }
   return out;
 }
+
+/**
+ * @deprecated Use `downloadMSTeamsAttachments` instead (supports all file types).
+ */
+export const downloadMSTeamsImageAttachments = downloadMSTeamsAttachments;

extensions/msteams/src/attachments/graph.ts

@@ -1,6 +1,6 @@
 import { getMSTeamsRuntime } from "../runtime.js";
-import { downloadMSTeamsImageAttachments } from "./download.js";
-import { GRAPH_ROOT, isRecord, normalizeContentType, resolveAllowedHosts } from "./shared.js";
+import { downloadMSTeamsAttachments } from "./download.js";
+import { GRAPH_ROOT, inferPlaceholder, isRecord, normalizeContentType, resolveAllowedHosts } from "./shared.js";
 import type {
   MSTeamsAccessTokenProvider,
   MSTeamsAttachmentLike,
@@ -128,11 +128,16 @@ function normalizeGraphAttachment(att: GraphAttachment): MSTeamsAttachmentLike {
   };
 }
 
-async function downloadGraphHostedImages(params: {
+/**
+ * Download all hosted content from a Teams message (images, documents, etc.).
+ * Renamed from downloadGraphHostedImages to support all file types.
+ */
+async function downloadGraphHostedContent(params: {
   accessToken: string;
   messageUrl: string;
   maxBytes: number;
   fetchFn?: typeof fetch;
+  preserveFilenames?: boolean;
 }): Promise<{ media: MSTeamsInboundMedia[]; status: number; count: number }> {
   const hosted = await fetchGraphCollection<GraphHostedContent>({
     url: `${params.messageUrl}/hostedContents`,
@@ -158,7 +163,7 @@ async function downloadGraphHostedImages(params: {
       buffer,
       headerMime: item.contentType ?? undefined,
     });
-    if (mime && !mime.startsWith("image/")) continue;
+    // Download any file type, not just images
     try {
       const saved = await getMSTeamsRuntime().channel.media.saveMediaBuffer(
         buffer,
@@ -169,7 +174,7 @@ async function downloadGraphHostedImages(params: {
       out.push({
         path: saved.path,
         contentType: saved.contentType,
-        placeholder: "<media:image>",
+        placeholder: inferPlaceholder({ contentType: saved.contentType }),
       });
     } catch {
       // Ignore save failures.
@@ -185,6 +190,8 @@ export async function downloadMSTeamsGraphMedia(params: {
   maxBytes: number;
   allowHosts?: string[];
   fetchFn?: typeof fetch;
+  /** When true, embeds original filename in stored path for later extraction. */
+  preserveFilenames?: boolean;
 }): Promise<MSTeamsGraphMediaResult> {
   if (!params.messageUrl || !params.tokenProvider) return { media: [] };
   const allowHosts = resolveAllowedHosts(params.allowHosts);
@@ -196,11 +203,83 @@ export async function downloadMSTeamsGraphMedia(params: {
     return { media: [], messageUrl, tokenError: true };
   }
 
-  const hosted = await downloadGraphHostedImages({
+  // Fetch the full message to get SharePoint file attachments (for group chats)
+  const fetchFn = params.fetchFn ?? fetch;
+  const sharePointMedia: MSTeamsInboundMedia[] = [];
+  const downloadedReferenceUrls = new Set<string>();
+  try {
+    const msgRes = await fetchFn(messageUrl, {
+      headers: { Authorization: `Bearer ${accessToken}` },
+    });
+    if (msgRes.ok) {
+      const msgData = (await msgRes.json()) as {
+        body?: { content?: string; contentType?: string };
+        attachments?: Array<{
+          id?: string;
+          contentUrl?: string;
+          contentType?: string;
+          name?: string;
+        }>;
+      };
+
+      // Extract SharePoint file attachments (contentType: "reference")
+      // Download any file type, not just images
+      const spAttachments = (msgData.attachments ?? []).filter(
+        (a) => a.contentType === "reference" && a.contentUrl && a.name,
+      );
+      for (const att of spAttachments) {
+        const name = att.name ?? "file";
+
+        try {
+          // SharePoint URLs need to be accessed via Graph shares API
+          const shareUrl = att.contentUrl!;
+          const encodedUrl = Buffer.from(shareUrl).toString("base64url");
+          const sharesUrl = `${GRAPH_ROOT}/shares/u!${encodedUrl}/driveItem/content`;
+
+          const spRes = await fetchFn(sharesUrl, {
+            headers: { Authorization: `Bearer ${accessToken}` },
+            redirect: "follow",
+          });
+
+          if (spRes.ok) {
+            const buffer = Buffer.from(await spRes.arrayBuffer());
+            if (buffer.byteLength <= params.maxBytes) {
+              const mime = await getMSTeamsRuntime().media.detectMime({
+                buffer,
+                headerMime: spRes.headers.get("content-type") ?? undefined,
+                filePath: name,
+              });
+              const originalFilename = params.preserveFilenames ? name : undefined;
+              const saved = await getMSTeamsRuntime().channel.media.saveMediaBuffer(
+                buffer,
+                mime ?? "application/octet-stream",
+                "inbound",
+                params.maxBytes,
+                originalFilename,
+              );
+              sharePointMedia.push({
+                path: saved.path,
+                contentType: saved.contentType,
+                placeholder: inferPlaceholder({ contentType: saved.contentType, fileName: name }),
+              });
+              downloadedReferenceUrls.add(shareUrl);
+            }
+          }
+        } catch {
+          // Ignore SharePoint download failures.
+        }
+      }
+    }
+  } catch {
+    // Ignore message fetch failures.
+  }
+
+  const hosted = await downloadGraphHostedContent({
     accessToken,
     messageUrl,
     maxBytes: params.maxBytes,
     fetchFn: params.fetchFn,
+    preserveFilenames: params.preserveFilenames,
   });
 
   const attachments = await fetchGraphCollection<GraphAttachment>({
@@ -210,18 +289,29 @@ export async function downloadMSTeamsGraphMedia(params: {
   });
 
   const normalizedAttachments = attachments.items.map(normalizeGraphAttachment);
-  const attachmentMedia = await downloadMSTeamsImageAttachments({
-    attachments: normalizedAttachments,
+  const filteredAttachments =
+    sharePointMedia.length > 0
+      ? normalizedAttachments.filter((att) => {
+          const contentType = att.contentType?.toLowerCase();
+          if (contentType !== "reference") return true;
+          const url = typeof att.contentUrl === "string" ? att.contentUrl : "";
+          if (!url) return true;
+          return !downloadedReferenceUrls.has(url);
+        })
+      : normalizedAttachments;
+  const attachmentMedia = await downloadMSTeamsAttachments({
+    attachments: filteredAttachments,
     maxBytes: params.maxBytes,
     tokenProvider: params.tokenProvider,
     allowHosts,
     fetchFn: params.fetchFn,
+    preserveFilenames: params.preserveFilenames,
   });
 
   return {
-    media: [...hosted.media, ...attachmentMedia],
+    media: [...sharePointMedia, ...hosted.media, ...attachmentMedia],
     hostedCount: hosted.count,
-    attachmentCount: attachments.items.length,
+    attachmentCount: filteredAttachments.length + sharePointMedia.length,
     hostedStatus: hosted.status,
     attachmentStatus: attachments.status,
     messageUrl,

extensions/msteams/src/attachments/shared.ts

@@ -37,6 +37,15 @@ export const DEFAULT_MEDIA_HOST_ALLOWLIST = [
   "statics.teams.cdn.office.net",
   "office.com",
   "office.net",
+  // Azure Media Services / Skype CDN for clipboard-pasted images
+  "asm.skype.com",
+  "ams.skype.com",
+  "media.ams.skype.com",
+  // Bot Framework attachment URLs
+  "trafficmanager.net",
+  "blob.core.windows.net",
+  "azureedge.net",
+  "microsoft.com",
 ] as const;
 
 export const GRAPH_ROOT = "https://graph.microsoft.com/v1.0";
@@ -85,6 +94,30 @@ export function isLikelyImageAttachment(att: MSTeamsAttachmentLike): boolean {
   return false;
 }
 
+/**
+ * Returns true if the attachment can be downloaded (any file type).
+ * Used when downloading all files, not just images.
+ */
+export function isDownloadableAttachment(att: MSTeamsAttachmentLike): boolean {
+  const contentType = normalizeContentType(att.contentType) ?? "";
+
+  // Teams file download info always has a downloadUrl
+  if (
+    contentType === "application/vnd.microsoft.teams.file.download.info" &&
+    isRecord(att.content) &&
+    typeof att.content.downloadUrl === "string"
+  ) {
+    return true;
+  }
+
+  // Any attachment with a contentUrl can be downloaded
+  if (typeof att.contentUrl === "string" && att.contentUrl.trim()) {
+    return true;
+  }
+
+  return false;
+}
+
 function isHtmlAttachment(att: MSTeamsAttachmentLike): boolean {
   const contentType = normalizeContentType(att.contentType) ?? "";
   return contentType.startsWith("text/html");

extensions/msteams/src/channel.ts

@@ -17,7 +17,7 @@ import {
   resolveMSTeamsChannelAllowlist,
   resolveMSTeamsUserAllowlist,
 } from "./resolve-allowlist.js";
-import { sendMessageMSTeams } from "./send.js";
+import { sendAdaptiveCardMSTeams, sendMessageMSTeams } from "./send.js";
 import { resolveMSTeamsCredentials } from "./token.js";
 import {
   listMSTeamsDirectoryGroupsLive,
@@ -64,6 +64,19 @@ export const msteamsPlugin: ChannelPlugin<ResolvedMSTeamsAccount> = {
     threads: true,
     media: true,
   },
+  agentPrompt: {
+    messageToolHints: () => [
+      "- Adaptive Cards supported. Use `action=send` with `card={type,version,body}` to send rich cards.",
+      "- MSTeams targeting: omit `target` to reply to the current conversation (auto-inferred). Explicit targets: `user:ID` or `user:Display Name` (requires Graph API) for DMs, `conversation:19:...@thread.tacv2` for groups/channels. Prefer IDs over display names for speed.",
+    ],
+  },
+  threading: {
+    buildToolContext: ({ context, hasRepliedRef }) => ({
+      currentChannelId: context.To?.trim() || undefined,
+      currentThreadTs: context.ReplyToId,
+      hasRepliedRef,
+    }),
+  },
   reload: { configPrefixes: ["channels.msteams"] },
   configSchema: buildChannelConfigSchema(MSTeamsConfigSchema),
   config: {
@@ -137,7 +150,12 @@ export const msteamsPlugin: ChannelPlugin<ResolvedMSTeamsAccount> = {
       looksLikeId: (raw) => {
         const trimmed = raw.trim();
         if (!trimmed) return false;
-        if (/^(conversation:|user:)/i.test(trimmed)) return true;
+        if (/^conversation:/i.test(trimmed)) return true;
+        if (/^user:/i.test(trimmed)) {
+          // Only treat as ID if the value after user: looks like a UUID
+          const id = trimmed.slice("user:".length).trim();
+          return /^[0-9a-fA-F-]{16,}$/.test(id);
+        }
         return trimmed.includes("@thread");
       },
       hint: "<conversationId|user:ID|conversation:ID>",
@@ -320,6 +338,50 @@ export const msteamsPlugin: ChannelPlugin<ResolvedMSTeamsAccount> = {
       if (!enabled) return [];
       return ["poll"] satisfies ChannelMessageActionName[];
     },
+    supportsCards: ({ cfg }) => {
+      return (
+        cfg.channels?.msteams?.enabled !== false &&
+        Boolean(resolveMSTeamsCredentials(cfg.channels?.msteams))
+      );
+    },
+    handleAction: async (ctx) => {
+      // Handle send action with card parameter
+      if (ctx.action === "send" && ctx.params.card) {
+        const card = ctx.params.card as Record<string, unknown>;
+        const to =
+          typeof ctx.params.to === "string"
+            ? ctx.params.to.trim()
+            : typeof ctx.params.target === "string"
+              ? ctx.params.target.trim()
+              : "";
+        if (!to) {
+          return {
+            isError: true,
+            content: [{ type: "text", text: "Card send requires a target (to)." }],
+          };
+        }
+        const result = await sendAdaptiveCardMSTeams({
+          cfg: ctx.cfg,
+          to,
+          card,
+        });
+        return {
+          content: [
+            {
+              type: "text",
+              text: JSON.stringify({
+                ok: true,
+                channel: "msteams",
+                messageId: result.messageId,
+                conversationId: result.conversationId,
+              }),
+            },
+          ],
+        };
+      }
+      // Return null to fall through to default handler
+      return null as never;
+    },
   },
   outbound: msteamsOutbound,
   status: {

extensions/msteams/src/file-consent-helpers.test.ts

@@ -0,0 +1,234 @@
+import { describe, expect, it, vi, beforeEach, afterEach } from "vitest";
+import { prepareFileConsentActivity, requiresFileConsent } from "./file-consent-helpers.js";
+import * as pendingUploads from "./pending-uploads.js";
+
+describe("requiresFileConsent", () => {
+  const thresholdBytes = 4 * 1024 * 1024; // 4MB
+
+  it("returns true for personal chat with non-image", () => {
+    expect(
+      requiresFileConsent({
+        conversationType: "personal",
+        contentType: "application/pdf",
+        bufferSize: 1000,
+        thresholdBytes,
+      }),
+    ).toBe(true);
+  });
+
+  it("returns true for personal chat with large image", () => {
+    expect(
+      requiresFileConsent({
+        conversationType: "personal",
+        contentType: "image/png",
+        bufferSize: 5 * 1024 * 1024, // 5MB
+        thresholdBytes,
+      }),
+    ).toBe(true);
+  });
+
+  it("returns false for personal chat with small image", () => {
+    expect(
+      requiresFileConsent({
+        conversationType: "personal",
+        contentType: "image/png",
+        bufferSize: 1000,
+        thresholdBytes,
+      }),
+    ).toBe(false);
+  });
+
+  it("returns false for group chat with large non-image", () => {
+    expect(
+      requiresFileConsent({
+        conversationType: "groupChat",
+        contentType: "application/pdf",
+        bufferSize: 5 * 1024 * 1024,
+        thresholdBytes,
+      }),
+    ).toBe(false);
+  });
+
+  it("returns false for channel with large non-image", () => {
+    expect(
+      requiresFileConsent({
+        conversationType: "channel",
+        contentType: "application/pdf",
+        bufferSize: 5 * 1024 * 1024,
+        thresholdBytes,
+      }),
+    ).toBe(false);
+  });
+
+  it("handles case-insensitive conversation type", () => {
+    expect(
+      requiresFileConsent({
+        conversationType: "Personal",
+        contentType: "application/pdf",
+        bufferSize: 1000,
+        thresholdBytes,
+      }),
+    ).toBe(true);
+
+    expect(
+      requiresFileConsent({
+        conversationType: "PERSONAL",
+        contentType: "application/pdf",
+        bufferSize: 1000,
+        thresholdBytes,
+      }),
+    ).toBe(true);
+  });
+
+  it("returns false when conversationType is undefined", () => {
+    expect(
+      requiresFileConsent({
+        conversationType: undefined,
+        contentType: "application/pdf",
+        bufferSize: 1000,
+        thresholdBytes,
+      }),
+    ).toBe(false);
+  });
+
+  it("returns true for personal chat when contentType is undefined (non-image)", () => {
+    expect(
+      requiresFileConsent({
+        conversationType: "personal",
+        contentType: undefined,
+        bufferSize: 1000,
+        thresholdBytes,
+      }),
+    ).toBe(true);
+  });
+
+  it("returns true for personal chat with file exactly at threshold", () => {
+    expect(
+      requiresFileConsent({
+        conversationType: "personal",
+        contentType: "image/jpeg",
+        bufferSize: thresholdBytes, // exactly 4MB
+        thresholdBytes,
+      }),
+    ).toBe(true);
+  });
+
+  it("returns false for personal chat with file just below threshold", () => {
+    expect(
+      requiresFileConsent({
+        conversationType: "personal",
+        contentType: "image/jpeg",
+        bufferSize: thresholdBytes - 1, // 4MB - 1 byte
+        thresholdBytes,
+      }),
+    ).toBe(false);
+  });
+});
+
+describe("prepareFileConsentActivity", () => {
+  const mockUploadId = "test-upload-id-123";
+
+  beforeEach(() => {
+    vi.spyOn(pendingUploads, "storePendingUpload").mockReturnValue(mockUploadId);
+  });
+
+  afterEach(() => {
+    vi.restoreAllMocks();
+  });
+
+  it("creates activity with consent card attachment", () => {
+    const result = prepareFileConsentActivity({
+      media: {
+        buffer: Buffer.from("test content"),
+        filename: "test.pdf",
+        contentType: "application/pdf",
+      },
+      conversationId: "conv123",
+      description: "My file",
+    });
+
+    expect(result.uploadId).toBe(mockUploadId);
+    expect(result.activity.type).toBe("message");
+    expect(result.activity.attachments).toHaveLength(1);
+
+    const attachment = (result.activity.attachments as unknown[])[0] as Record<string, unknown>;
+    expect(attachment.contentType).toBe("application/vnd.microsoft.teams.card.file.consent");
+    expect(attachment.name).toBe("test.pdf");
+  });
+
+  it("stores pending upload with correct data", () => {
+    const buffer = Buffer.from("test content");
+    prepareFileConsentActivity({
+      media: {
+        buffer,
+        filename: "test.pdf",
+        contentType: "application/pdf",
+      },
+      conversationId: "conv123",
+      description: "My file",
+    });
+
+    expect(pendingUploads.storePendingUpload).toHaveBeenCalledWith({
+      buffer,
+      filename: "test.pdf",
+      contentType: "application/pdf",
+      conversationId: "conv123",
+    });
+  });
+
+  it("uses default description when not provided", () => {
+    const result = prepareFileConsentActivity({
+      media: {
+        buffer: Buffer.from("test"),
+        filename: "document.docx",
+        contentType: "application/vnd.openxmlformats-officedocument.wordprocessingml.document",
+      },
+      conversationId: "conv456",
+    });
+
+    const attachment = (result.activity.attachments as unknown[])[0] as Record<string, { description: string }>;
+    expect(attachment.content.description).toBe("File: document.docx");
+  });
+
+  it("uses provided description", () => {
+    const result = prepareFileConsentActivity({
+      media: {
+        buffer: Buffer.from("test"),
+        filename: "report.pdf",
+        contentType: "application/pdf",
+      },
+      conversationId: "conv789",
+      description: "Q4 Financial Report",
+    });
+
+    const attachment = (result.activity.attachments as unknown[])[0] as Record<string, { description: string }>;
+    expect(attachment.content.description).toBe("Q4 Financial Report");
+  });
+
+  it("includes uploadId in consent card context", () => {
+    const result = prepareFileConsentActivity({
+      media: {
+        buffer: Buffer.from("test"),
+        filename: "file.txt",
+        contentType: "text/plain",
+      },
+      conversationId: "conv000",
+    });
+
+    const attachment = (result.activity.attachments as unknown[])[0] as Record<string, { acceptContext: { uploadId: string } }>;
+    expect(attachment.content.acceptContext.uploadId).toBe(mockUploadId);
+  });
+
+  it("handles media without contentType", () => {
+    const result = prepareFileConsentActivity({
+      media: {
+        buffer: Buffer.from("binary data"),
+        filename: "unknown.bin",
+      },
+      conversationId: "conv111",
+    });
+
+    expect(result.uploadId).toBe(mockUploadId);
+    expect(result.activity.type).toBe("message");
+  });
+});

extensions/msteams/src/file-consent-helpers.ts

@@ -0,0 +1,73 @@
+/**
+ * Shared helpers for FileConsentCard flow in MSTeams.
+ *
+ * FileConsentCard is required for:
+ * - Personal (1:1) chats with large files (>=4MB)
+ * - Personal chats with non-image files (PDFs, documents, etc.)
+ *
+ * This module consolidates the logic used by both send.ts (proactive sends)
+ * and messenger.ts (reply path) to avoid duplication.
+ */
+
+import { buildFileConsentCard } from "./file-consent.js";
+import { storePendingUpload } from "./pending-uploads.js";
+
+export type FileConsentMedia = {
+  buffer: Buffer;
+  filename: string;
+  contentType?: string;
+};
+
+export type FileConsentActivityResult = {
+  activity: Record<string, unknown>;
+  uploadId: string;
+};
+
+/**
+ * Prepare a FileConsentCard activity for large files or non-images in personal chats.
+ * Returns the activity object and uploadId - caller is responsible for sending.
+ */
+export function prepareFileConsentActivity(params: {
+  media: FileConsentMedia;
+  conversationId: string;
+  description?: string;
+}): FileConsentActivityResult {
+  const { media, conversationId, description } = params;
+
+  const uploadId = storePendingUpload({
+    buffer: media.buffer,
+    filename: media.filename,
+    contentType: media.contentType,
+    conversationId,
+  });
+
+  const consentCard = buildFileConsentCard({
+    filename: media.filename,
+    description: description || `File: ${media.filename}`,
+    sizeInBytes: media.buffer.length,
+    context: { uploadId },
+  });
+
+  const activity: Record<string, unknown> = {
+    type: "message",
+    attachments: [consentCard],
+  };
+
+  return { activity, uploadId };
+}
+
+/**
+ * Check if a file requires FileConsentCard flow.
+ * True for: personal chat AND (large file OR non-image)
+ */
+export function requiresFileConsent(params: {
+  conversationType: string | undefined;
+  contentType: string | undefined;
+  bufferSize: number;
+  thresholdBytes: number;
+}): boolean {
+  const isPersonal = params.conversationType?.toLowerCase() === "personal";
+  const isImage = params.contentType?.startsWith("image/") ?? false;
+  const isLargeFile = params.bufferSize >= params.thresholdBytes;
+  return isPersonal && (isLargeFile || !isImage);
+}

extensions/msteams/src/file-consent.ts

@@ -0,0 +1,122 @@
+/**
+ * FileConsentCard utilities for MS Teams large file uploads (>4MB) in personal chats.
+ *
+ * Teams requires user consent before the bot can upload large files. This module provides
+ * utilities for:
+ * - Building FileConsentCard attachments (to request upload permission)
+ * - Building FileInfoCard attachments (to confirm upload completion)
+ * - Parsing fileConsent/invoke activities
+ */
+
+export interface FileConsentCardParams {
+  filename: string;
+  description?: string;
+  sizeInBytes: number;
+  /** Custom context data to include in the card (passed back in the invoke) */
+  context?: Record<string, unknown>;
+}
+
+export interface FileInfoCardParams {
+  filename: string;
+  contentUrl: string;
+  uniqueId: string;
+  fileType: string;
+}
+
+/**
+ * Build a FileConsentCard attachment for requesting upload permission.
+ * Use this for files >= 4MB in personal (1:1) chats.
+ */
+export function buildFileConsentCard(params: FileConsentCardParams) {
+  return {
+    contentType: "application/vnd.microsoft.teams.card.file.consent",
+    name: params.filename,
+    content: {
+      description: params.description ?? `File: ${params.filename}`,
+      sizeInBytes: params.sizeInBytes,
+      acceptContext: { filename: params.filename, ...params.context },
+      declineContext: { filename: params.filename, ...params.context },
+    },
+  };
+}
+
+/**
+ * Build a FileInfoCard attachment for confirming upload completion.
+ * Send this after successfully uploading the file to the consent URL.
+ */
+export function buildFileInfoCard(params: FileInfoCardParams) {
+  return {
+    contentType: "application/vnd.microsoft.teams.card.file.info",
+    contentUrl: params.contentUrl,
+    name: params.filename,
+    content: {
+      uniqueId: params.uniqueId,
+      fileType: params.fileType,
+    },
+  };
+}
+
+export interface FileConsentUploadInfo {
+  name: string;
+  uploadUrl: string;
+  contentUrl: string;
+  uniqueId: string;
+  fileType: string;
+}
+
+export interface FileConsentResponse {
+  action: "accept" | "decline";
+  uploadInfo?: FileConsentUploadInfo;
+  context?: Record<string, unknown>;
+}
+
+/**
+ * Parse a fileConsent/invoke activity.
+ * Returns null if the activity is not a file consent invoke.
+ */
+export function parseFileConsentInvoke(activity: {
+  name?: string;
+  value?: unknown;
+}): FileConsentResponse | null {
+  if (activity.name !== "fileConsent/invoke") return null;
+
+  const value = activity.value as {
+    type?: string;
+    action?: string;
+    uploadInfo?: FileConsentUploadInfo;
+    context?: Record<string, unknown>;
+  };
+
+  if (value?.type !== "fileUpload") return null;
+
+  return {
+    action: value.action === "accept" ? "accept" : "decline",
+    uploadInfo: value.uploadInfo,
+    context: value.context,
+  };
+}
+
+/**
+ * Upload a file to the consent URL provided by Teams.
+ * The URL is provided in the fileConsent/invoke response after user accepts.
+ */
+export async function uploadToConsentUrl(params: {
+  url: string;
+  buffer: Buffer;
+  contentType?: string;
+  fetchFn?: typeof fetch;
+}): Promise<void> {
+  const fetchFn = params.fetchFn ?? fetch;
+  const res = await fetchFn(params.url, {
+    method: "PUT",
+    headers: {
+      "Content-Type": params.contentType ?? "application/octet-stream",
+      "Content-Range": `bytes 0-${params.buffer.length - 1}/${params.buffer.length}`,
+    },
+    body: new Uint8Array(params.buffer),
+  });
+
+  if (!res.ok) {
+    throw new Error(`File upload to consent URL failed: ${res.status} ${res.statusText}`);
+  }
+}

extensions/msteams/src/graph-chat.ts

@@ -0,0 +1,52 @@
+/**
+ * Native Teams file card attachments for Bot Framework.
+ *
+ * The Bot Framework SDK supports `application/vnd.microsoft.teams.card.file.info`
+ * content type which produces native Teams file cards.
+ *
+ * @see https://learn.microsoft.com/en-us/microsoftteams/platform/bots/how-to/bots-filesv4
+ */
+
+import type { DriveItemProperties } from "./graph-upload.js";
+
+/**
+ * Build a native Teams file card attachment for Bot Framework.
+ *
+ * This uses the `application/vnd.microsoft.teams.card.file.info` content type
+ * which is supported by Bot Framework and produces native Teams file cards
+ * (the same display as when a user manually shares a file).
+ *
+ * @param file - DriveItem properties from getDriveItemProperties()
+ * @returns Attachment object for Bot Framework sendActivity()
+ */
+export function buildTeamsFileInfoCard(file: DriveItemProperties): {
+  contentType: string;
+  contentUrl: string;
+  name: string;
+  content: {
+    uniqueId: string;
+    fileType: string;
+  };
+} {
+  // Extract unique ID from eTag (remove quotes, braces, and version suffix)
+  // Example eTag formats: "{GUID},version" or "\"{GUID},version\""
+  const rawETag = file.eTag;
+  const uniqueId = rawETag
+    .replace(/^["']|["']$/g, "") // Remove outer quotes
+    .replace(/[{}]/g, "") // Remove curly braces
+    .split(",")[0] ?? rawETag; // Take the GUID part before comma
+
+  // Extract file extension from filename
+  const lastDot = file.name.lastIndexOf(".");
+  const fileType = lastDot >= 0 ? file.name.slice(lastDot + 1).toLowerCase() : "";
+
+  return {
+    contentType: "application/vnd.microsoft.teams.card.file.info",
+    contentUrl: file.webDavUrl,
+    name: file.name,
+    content: {
+      uniqueId,
+      fileType,
+    },
+  };
+}

extensions/msteams/src/graph-upload.ts

@@ -0,0 +1,445 @@
+/**
+ * OneDrive/SharePoint upload utilities for MS Teams file sending.
+ *
+ * For group chats and channels, files are uploaded to SharePoint and shared via a link.
+ * This module provides utilities for:
+ * - Uploading files to OneDrive (personal scope - now deprecated for bot use)
+ * - Uploading files to SharePoint (group/channel scope)
+ * - Creating sharing links (organization-wide or per-user)
+ * - Getting chat members for per-user sharing
+ */
+
+import type { MSTeamsAccessTokenProvider } from "./attachments/types.js";
+
+const GRAPH_ROOT = "https://graph.microsoft.com/v1.0";
+const GRAPH_BETA = "https://graph.microsoft.com/beta";
+const GRAPH_SCOPE = "https://graph.microsoft.com/.default";
+
+export interface OneDriveUploadResult {
+  id: string;
+  webUrl: string;
+  name: string;
+}
+
+/**
+ * Upload a file to the user's OneDrive root folder.
+ * For larger files, this uses the simple upload endpoint (up to 4MB).
+ * TODO: For files >4MB, implement resumable upload session.
+ */
+export async function uploadToOneDrive(params: {
+  buffer: Buffer;
+  filename: string;
+  contentType?: string;
+  tokenProvider: MSTeamsAccessTokenProvider;
+  fetchFn?: typeof fetch;
+}): Promise<OneDriveUploadResult> {
+  const fetchFn = params.fetchFn ?? fetch;
+  const token = await params.tokenProvider.getAccessToken(GRAPH_SCOPE);
+
+  // Use "ClawdbotShared" folder to organize bot-uploaded files
+  const uploadPath = `/ClawdbotShared/${encodeURIComponent(params.filename)}`;
+
+  const res = await fetchFn(`${GRAPH_ROOT}/me/drive/root:${uploadPath}:/content`, {
+    method: "PUT",
+    headers: {
+      Authorization: `Bearer ${token}`,
+      "Content-Type": params.contentType ?? "application/octet-stream",
+    },
+    body: new Uint8Array(params.buffer),
+  });
+
+  if (!res.ok) {
+    const body = await res.text().catch(() => "");
+    throw new Error(`OneDrive upload failed: ${res.status} ${res.statusText} - ${body}`);
+  }
+
+  const data = (await res.json()) as {
+    id?: string;
+    webUrl?: string;
+    name?: string;
+  };
+
+  if (!data.id || !data.webUrl || !data.name) {
+    throw new Error("OneDrive upload response missing required fields");
+  }
+
+  return {
+    id: data.id,
+    webUrl: data.webUrl,
+    name: data.name,
+  };
+}
+
+export interface OneDriveSharingLink {
+  webUrl: string;
+}
+
+/**
+ * Create a sharing link for a OneDrive file.
+ * The link allows organization members to view the file.
+ */
+export async function createSharingLink(params: {
+  itemId: string;
+  tokenProvider: MSTeamsAccessTokenProvider;
+  /** Sharing scope: "organization" (default) or "anonymous" */
+  scope?: "organization" | "anonymous";
+  fetchFn?: typeof fetch;
+}): Promise<OneDriveSharingLink> {
+  const fetchFn = params.fetchFn ?? fetch;
+  const token = await params.tokenProvider.getAccessToken(GRAPH_SCOPE);
+
+  const res = await fetchFn(`${GRAPH_ROOT}/me/drive/items/${params.itemId}/createLink`, {
+    method: "POST",
+    headers: {
+      Authorization: `Bearer ${token}`,
+      "Content-Type": "application/json",
+    },
+    body: JSON.stringify({
+      type: "view",
+      scope: params.scope ?? "organization",
+    }),
+  });
+
+  if (!res.ok) {
+    const body = await res.text().catch(() => "");
+    throw new Error(`Create sharing link failed: ${res.status} ${res.statusText} - ${body}`);
+  }
+
+  const data = (await res.json()) as {
+    link?: { webUrl?: string };
+  };
+
+  if (!data.link?.webUrl) {
+    throw new Error("Create sharing link response missing webUrl");
+  }
+
+  return {
+    webUrl: data.link.webUrl,
+  };
+}
+
+/**
+ * Upload a file to OneDrive and create a sharing link.
+ * Convenience function for the common case.
+ */
+export async function uploadAndShareOneDrive(params: {
+  buffer: Buffer;
+  filename: string;
+  contentType?: string;
+  tokenProvider: MSTeamsAccessTokenProvider;
+  scope?: "organization" | "anonymous";
+  fetchFn?: typeof fetch;
+}): Promise<{
+  itemId: string;
+  webUrl: string;
+  shareUrl: string;
+  name: string;
+}> {
+  const uploaded = await uploadToOneDrive({
+    buffer: params.buffer,
+    filename: params.filename,
+    contentType: params.contentType,
+    tokenProvider: params.tokenProvider,
+    fetchFn: params.fetchFn,
+  });
+
+  const shareLink = await createSharingLink({
+    itemId: uploaded.id,
+    tokenProvider: params.tokenProvider,
+    scope: params.scope,
+    fetchFn: params.fetchFn,
+  });
+
+  return {
+    itemId: uploaded.id,
+    webUrl: uploaded.webUrl,
+    shareUrl: shareLink.webUrl,
+    name: uploaded.name,
+  };
+}
+
+// ============================================================================
+// SharePoint upload functions for group chats and channels
+// ============================================================================
+
+/**
+ * Upload a file to a SharePoint site.
+ * This is used for group chats and channels where /me/drive doesn't work for bots.
+ *
+ * @param params.siteId - SharePoint site ID (e.g., "contoso.sharepoint.com,guid1,guid2")
+ */
+export async function uploadToSharePoint(params: {
+  buffer: Buffer;
+  filename: string;
+  contentType?: string;
+  tokenProvider: MSTeamsAccessTokenProvider;
+  siteId: string;
+  fetchFn?: typeof fetch;
+}): Promise<OneDriveUploadResult> {
+  const fetchFn = params.fetchFn ?? fetch;
+  const token = await params.tokenProvider.getAccessToken(GRAPH_SCOPE);
+
+  // Use "ClawdbotShared" folder to organize bot-uploaded files
+  const uploadPath = `/ClawdbotShared/${encodeURIComponent(params.filename)}`;
+
+  const res = await fetchFn(`${GRAPH_ROOT}/sites/${params.siteId}/drive/root:${uploadPath}:/content`, {
+    method: "PUT",
+    headers: {
+      Authorization: `Bearer ${token}`,
+      "Content-Type": params.contentType ?? "application/octet-stream",
+    },
+    body: new Uint8Array(params.buffer),
+  });
+
+  if (!res.ok) {
+    const body = await res.text().catch(() => "");
+    throw new Error(`SharePoint upload failed: ${res.status} ${res.statusText} - ${body}`);
+  }
+
+  const data = (await res.json()) as {
+    id?: string;
+    webUrl?: string;
+    name?: string;
+  };
+
+  if (!data.id || !data.webUrl || !data.name) {
+    throw new Error("SharePoint upload response missing required fields");
+  }
+
+  return {
+    id: data.id,
+    webUrl: data.webUrl,
+    name: data.name,
+  };
+}
+
+export interface ChatMember {
+  aadObjectId: string;
+  displayName?: string;
+}
+
+/**
+ * Properties needed for native Teams file card attachments.
+ * The eTag is used as the attachment ID and webDavUrl as the contentUrl.
+ */
+export interface DriveItemProperties {
+  /** The eTag of the driveItem (used as attachment ID) */
+  eTag: string;
+  /** The WebDAV URL of the driveItem (used as contentUrl for reference attachment) */
+  webDavUrl: string;
+  /** The filename */
+  name: string;
+}
+
+/**
+ * Get driveItem properties needed for native Teams file card attachments.
+ * This fetches the eTag and webDavUrl which are required for "reference" type attachments.
+ *
+ * @param params.siteId - SharePoint site ID
+ * @param params.itemId - The driveItem ID (returned from upload)
+ */
+export async function getDriveItemProperties(params: {
+  siteId: string;
+  itemId: string;
+  tokenProvider: MSTeamsAccessTokenProvider;
+  fetchFn?: typeof fetch;
+}): Promise<DriveItemProperties> {
+  const fetchFn = params.fetchFn ?? fetch;
+  const token = await params.tokenProvider.getAccessToken(GRAPH_SCOPE);
+
+  const res = await fetchFn(
+    `${GRAPH_ROOT}/sites/${params.siteId}/drive/items/${params.itemId}?$select=eTag,webDavUrl,name`,
+    { headers: { Authorization: `Bearer ${token}` } },
+  );
+
+  if (!res.ok) {
+    const body = await res.text().catch(() => "");
+    throw new Error(`Get driveItem properties failed: ${res.status} ${res.statusText} - ${body}`);
+  }
+
+  const data = (await res.json()) as {
+    eTag?: string;
+    webDavUrl?: string;
+    name?: string;
+  };
+
+  if (!data.eTag || !data.webDavUrl || !data.name) {
+    throw new Error("DriveItem response missing required properties (eTag, webDavUrl, or name)");
+  }
+
+  return {
+    eTag: data.eTag,
+    webDavUrl: data.webDavUrl,
+    name: data.name,
+  };
+}
+
+/**
+ * Get members of a Teams chat for per-user sharing.
+ * Used to create sharing links scoped to only the chat participants.
+ */
+export async function getChatMembers(params: {
+  chatId: string;
+  tokenProvider: MSTeamsAccessTokenProvider;
+  fetchFn?: typeof fetch;
+}): Promise<ChatMember[]> {
+  const fetchFn = params.fetchFn ?? fetch;
+  const token = await params.tokenProvider.getAccessToken(GRAPH_SCOPE);
+
+  const res = await fetchFn(`${GRAPH_ROOT}/chats/${params.chatId}/members`, {
+    headers: { Authorization: `Bearer ${token}` },
+  });
+
+  if (!res.ok) {
+    const body = await res.text().catch(() => "");
+    throw new Error(`Get chat members failed: ${res.status} ${res.statusText} - ${body}`);
+  }
+
+  const data = (await res.json()) as {
+    value?: Array<{
+      userId?: string;
+      displayName?: string;
+    }>;
+  };
+
+  return (data.value ?? [])
+    .map((m) => ({
+      aadObjectId: m.userId ?? "",
+      displayName: m.displayName,
+    }))
+    .filter((m) => m.aadObjectId);
+}
+
+/**
+ * Create a sharing link for a SharePoint drive item.
+ * For organization scope (default), uses v1.0 API.
+ * For per-user scope, uses beta API with recipients.
+ */
+export async function createSharePointSharingLink(params: {
+  siteId: string;
+  itemId: string;
+  tokenProvider: MSTeamsAccessTokenProvider;
+  /** Sharing scope: "organization" (default) or "users" (per-user with recipients) */
+  scope?: "organization" | "users";
+  /** Required when scope is "users": AAD object IDs of recipients */
+  recipientObjectIds?: string[];
+  fetchFn?: typeof fetch;
+}): Promise<OneDriveSharingLink> {
+  const fetchFn = params.fetchFn ?? fetch;
+  const token = await params.tokenProvider.getAccessToken(GRAPH_SCOPE);
+  const scope = params.scope ?? "organization";
+
+  // Per-user sharing requires beta API
+  const apiRoot = scope === "users" ? GRAPH_BETA : GRAPH_ROOT;
+
+  const body: Record<string, unknown> = {
+    type: "view",
+    scope: scope === "users" ? "users" : "organization",
+  };
+
+  // Add recipients for per-user sharing
+  if (scope === "users" && params.recipientObjectIds?.length) {
+    body.recipients = params.recipientObjectIds.map((id) => ({ objectId: id }));
+  }
+
+  const res = await fetchFn(`${apiRoot}/sites/${params.siteId}/drive/items/${params.itemId}/createLink`, {
+    method: "POST",
+    headers: {
+      Authorization: `Bearer ${token}`,
+      "Content-Type": "application/json",
+    },
+    body: JSON.stringify(body),
+  });
+
+  if (!res.ok) {
+    const respBody = await res.text().catch(() => "");
+    throw new Error(`Create SharePoint sharing link failed: ${res.status} ${res.statusText} - ${respBody}`);
+  }
+
+  const data = (await res.json()) as {
+    link?: { webUrl?: string };
+  };
+
+  if (!data.link?.webUrl) {
+    throw new Error("Create SharePoint sharing link response missing webUrl");
+  }
+
+  return {
+    webUrl: data.link.webUrl,
+  };
+}
+
+/**
+ * Upload a file to SharePoint and create a sharing link.
+ *
+ * For group chats, this creates a per-user sharing link scoped to chat members.
+ * For channels, this creates an organization-wide sharing link.
+ *
+ * @param params.siteId - SharePoint site ID
+ * @param params.chatId - Optional chat ID for per-user sharing (group chats)
+ * @param params.usePerUserSharing - Whether to use per-user sharing (requires beta API + Chat.Read.All)
+ */
+export async function uploadAndShareSharePoint(params: {
+  buffer: Buffer;
+  filename: string;
+  contentType?: string;
+  tokenProvider: MSTeamsAccessTokenProvider;
+  siteId: string;
+  chatId?: string;
+  usePerUserSharing?: boolean;
+  fetchFn?: typeof fetch;
+}): Promise<{
+  itemId: string;
+  webUrl: string;
+  shareUrl: string;
+  name: string;
+}> {
+  // 1. Upload file to SharePoint
+  const uploaded = await uploadToSharePoint({
+    buffer: params.buffer,
+    filename: params.filename,
+    contentType: params.contentType,
+    tokenProvider: params.tokenProvider,
+    siteId: params.siteId,
+    fetchFn: params.fetchFn,
+  });
+
+  // 2. Determine sharing scope
+  let scope: "organization" | "users" = "organization";
+  let recipientObjectIds: string[] | undefined;
+
+  if (params.usePerUserSharing && params.chatId) {
+    try {
+      const members = await getChatMembers({
+        chatId: params.chatId,
+        tokenProvider: params.tokenProvider,
+        fetchFn: params.fetchFn,
+      });
+
+      if (members.length > 0) {
+        scope = "users";
+        recipientObjectIds = members.map((m) => m.aadObjectId);
+      }
+    } catch {
+      // Fall back to organization scope if we can't get chat members
+      // (e.g., missing Chat.Read.All permission)
+    }
+  }
+
+  // 3. Create sharing link
+  const shareLink = await createSharePointSharingLink({
+    siteId: params.siteId,
+    itemId: uploaded.id,
+    tokenProvider: params.tokenProvider,
+    scope,
+    recipientObjectIds,
+    fetchFn: params.fetchFn,
+  });
+
+  return {
+    itemId: uploaded.id,
+    webUrl: uploaded.webUrl,
+    shareUrl: shareLink.webUrl,
+    name: uploaded.name,
+  };
+}

extensions/msteams/src/media-helpers.test.ts

@@ -0,0 +1,186 @@
+import { describe, expect, it } from "vitest";
+
+import { extractFilename, extractMessageId, getMimeType, isLocalPath } from "./media-helpers.js";
+
+describe("msteams media-helpers", () => {
+  describe("getMimeType", () => {
+    it("detects png from URL", async () => {
+      expect(await getMimeType("https://example.com/image.png")).toBe("image/png");
+    });
+
+    it("detects jpeg from URL (both extensions)", async () => {
+      expect(await getMimeType("https://example.com/photo.jpg")).toBe("image/jpeg");
+      expect(await getMimeType("https://example.com/photo.jpeg")).toBe("image/jpeg");
+    });
+
+    it("detects gif from URL", async () => {
+      expect(await getMimeType("https://example.com/anim.gif")).toBe("image/gif");
+    });
+
+    it("detects webp from URL", async () => {
+      expect(await getMimeType("https://example.com/modern.webp")).toBe("image/webp");
+    });
+
+    it("handles URLs with query strings", async () => {
+      expect(await getMimeType("https://example.com/image.png?v=123")).toBe("image/png");
+    });
+
+    it("handles data URLs", async () => {
+      expect(await getMimeType("data:image/png;base64,iVBORw0KGgo=")).toBe("image/png");
+      expect(await getMimeType("data:image/jpeg;base64,/9j/4AAQ")).toBe("image/jpeg");
+      expect(await getMimeType("data:image/gif;base64,R0lGOD")).toBe("image/gif");
+    });
+
+    it("handles data URLs without base64", async () => {
+      expect(await getMimeType("data:image/svg+xml,%3Csvg")).toBe("image/svg+xml");
+    });
+
+    it("handles local paths", async () => {
+      expect(await getMimeType("/tmp/image.png")).toBe("image/png");
+      expect(await getMimeType("/Users/test/photo.jpg")).toBe("image/jpeg");
+    });
+
+    it("handles tilde paths", async () => {
+      expect(await getMimeType("~/Downloads/image.gif")).toBe("image/gif");
+    });
+
+    it("defaults to application/octet-stream for unknown extensions", async () => {
+      expect(await getMimeType("https://example.com/image")).toBe("application/octet-stream");
+      expect(await getMimeType("https://example.com/image.unknown")).toBe("application/octet-stream");
+    });
+
+    it("is case-insensitive", async () => {
+      expect(await getMimeType("https://example.com/IMAGE.PNG")).toBe("image/png");
+      expect(await getMimeType("https://example.com/Photo.JPEG")).toBe("image/jpeg");
+    });
+
+    it("detects document types", async () => {
+      expect(await getMimeType("https://example.com/doc.pdf")).toBe("application/pdf");
+      expect(await getMimeType("https://example.com/doc.docx")).toBe(
+        "application/vnd.openxmlformats-officedocument.wordprocessingml.document",
+      );
+      expect(await getMimeType("https://example.com/spreadsheet.xlsx")).toBe(
+        "application/vnd.openxmlformats-officedocument.spreadsheetml.sheet",
+      );
+    });
+  });
+
+  describe("extractFilename", () => {
+    it("extracts filename from URL with extension", async () => {
+      expect(await extractFilename("https://example.com/photo.jpg")).toBe("photo.jpg");
+    });
+
+    it("extracts filename from URL with path", async () => {
+      expect(await extractFilename("https://example.com/images/2024/photo.png")).toBe("photo.png");
+    });
+
+    it("handles URLs without extension by deriving from MIME", async () => {
+      // Now defaults to application/octet-stream → .bin fallback
+      expect(await extractFilename("https://example.com/images/photo")).toBe("photo.bin");
+    });
+
+    it("handles data URLs", async () => {
+      expect(await extractFilename("data:image/png;base64,iVBORw0KGgo=")).toBe("image.png");
+      expect(await extractFilename("data:image/jpeg;base64,/9j/4AAQ")).toBe("image.jpg");
+    });
+
+    it("handles document data URLs", async () => {
+      expect(await extractFilename("data:application/pdf;base64,JVBERi0")).toBe("file.pdf");
+    });
+
+    it("handles local paths", async () => {
+      expect(await extractFilename("/tmp/screenshot.png")).toBe("screenshot.png");
+      expect(await extractFilename("/Users/test/photo.jpg")).toBe("photo.jpg");
+    });
+
+    it("handles tilde paths", async () => {
+      expect(await extractFilename("~/Downloads/image.gif")).toBe("image.gif");
+    });
+
+    it("returns fallback for empty URL", async () => {
+      expect(await extractFilename("")).toBe("file.bin");
+    });
+
+    it("extracts original filename from embedded pattern", async () => {
+      // Pattern: {original}---{uuid}.{ext}
+      expect(
+        await extractFilename("/media/inbound/report---a1b2c3d4-e5f6-7890-abcd-ef1234567890.pdf"),
+      ).toBe("report.pdf");
+    });
+
+    it("extracts original filename with uppercase UUID", async () => {
+      expect(
+        await extractFilename("/media/inbound/Document---A1B2C3D4-E5F6-7890-ABCD-EF1234567890.docx"),
+      ).toBe("Document.docx");
+    });
+
+    it("falls back to UUID filename for legacy paths", async () => {
+      // UUID-only filename (legacy format, no embedded name)
+      expect(
+        await extractFilename("/media/inbound/a1b2c3d4-e5f6-7890-abcd-ef1234567890.pdf"),
+      ).toBe("a1b2c3d4-e5f6-7890-abcd-ef1234567890.pdf");
+    });
+
+    it("handles --- in filename without valid UUID pattern", async () => {
+      // foo---bar.txt (bar is not a valid UUID)
+      expect(await extractFilename("/media/inbound/foo---bar.txt")).toBe("foo---bar.txt");
+    });
+  });
+
+  describe("isLocalPath", () => {
+    it("returns true for file:// URLs", () => {
+      expect(isLocalPath("file:///tmp/image.png")).toBe(true);
+      expect(isLocalPath("file://localhost/tmp/image.png")).toBe(true);
+    });
+
+    it("returns true for absolute paths", () => {
+      expect(isLocalPath("/tmp/image.png")).toBe(true);
+      expect(isLocalPath("/Users/test/photo.jpg")).toBe(true);
+    });
+
+    it("returns true for tilde paths", () => {
+      expect(isLocalPath("~/Downloads/image.png")).toBe(true);
+    });
+
+    it("returns false for http URLs", () => {
+      expect(isLocalPath("http://example.com/image.png")).toBe(false);
+      expect(isLocalPath("https://example.com/image.png")).toBe(false);
+    });
+
+    it("returns false for data URLs", () => {
+      expect(isLocalPath("data:image/png;base64,iVBORw0KGgo=")).toBe(false);
+    });
+  });
+
+  describe("extractMessageId", () => {
+    it("extracts id from valid response", () => {
+      expect(extractMessageId({ id: "msg123" })).toBe("msg123");
+    });
+
+    it("returns null for missing id", () => {
+      expect(extractMessageId({ foo: "bar" })).toBeNull();
+    });
+
+    it("returns null for empty id", () => {
+      expect(extractMessageId({ id: "" })).toBeNull();
+    });
+
+    it("returns null for non-string id", () => {
+      expect(extractMessageId({ id: 123 })).toBeNull();
+      expect(extractMessageId({ id: null })).toBeNull();
+    });
+
+    it("returns null for null response", () => {
+      expect(extractMessageId(null)).toBeNull();
+    });
+
+    it("returns null for undefined response", () => {
+      expect(extractMessageId(undefined)).toBeNull();
+    });
+
+    it("returns null for non-object response", () => {
+      expect(extractMessageId("string")).toBeNull();
+      expect(extractMessageId(123)).toBeNull();
+    });
+  });
+});

extensions/msteams/src/media-helpers.ts

@@ -0,0 +1,77 @@
+/**
+ * MIME type detection and filename extraction for MSTeams media attachments.
+ */
+
+import path from "node:path";
+
+import {
+  detectMime,
+  extensionForMime,
+  extractOriginalFilename,
+  getFileExtension,
+} from "clawdbot/plugin-sdk";
+
+/**
+ * Detect MIME type from URL extension or data URL.
+ * Uses shared MIME detection for consistency with core handling.
+ */
+export async function getMimeType(url: string): Promise<string> {
+  // Handle data URLs: data:image/png;base64,...
+  if (url.startsWith("data:")) {
+    const match = url.match(/^data:([^;,]+)/);
+    if (match?.[1]) return match[1];
+  }
+
+  // Use shared MIME detection (extension-based for URLs)
+  const detected = await detectMime({ filePath: url });
+  return detected ?? "application/octet-stream";
+}
+
+/**
+ * Extract filename from URL or local path.
+ * For local paths, extracts original filename if stored with embedded name pattern.
+ * Falls back to deriving the extension from MIME type when no extension present.
+ */
+export async function extractFilename(url: string): Promise<string> {
+  // Handle data URLs: derive extension from MIME
+  if (url.startsWith("data:")) {
+    const mime = await getMimeType(url);
+    const ext = extensionForMime(mime) ?? ".bin";
+    const prefix = mime.startsWith("image/") ? "image" : "file";
+    return `${prefix}${ext}`;
+  }
+
+  // Try to extract from URL pathname
+  try {
+    const pathname = new URL(url).pathname;
+    const basename = path.basename(pathname);
+    const existingExt = getFileExtension(pathname);
+    if (basename && existingExt) return basename;
+    // No extension in URL, derive from MIME
+    const mime = await getMimeType(url);
+    const ext = extensionForMime(mime) ?? ".bin";
+    const prefix = mime.startsWith("image/") ? "image" : "file";
+    return basename ? `${basename}${ext}` : `${prefix}${ext}`;
+  } catch {
+    // Local paths - use extractOriginalFilename to extract embedded original name
+    return extractOriginalFilename(url);
+  }
+}
+
+/**
+ * Check if a URL refers to a local file path.
+ */
+export function isLocalPath(url: string): boolean {
+  return url.startsWith("file://") || url.startsWith("/") || url.startsWith("~");
+}
+
+/**
+ * Extract the message ID from a Bot Framework response.
+ */
+export function extractMessageId(response: unknown): string | null {
+  if (!response || typeof response !== "object") return null;
+  if (!("id" in response)) return null;
+  const { id } = response as { id?: unknown };
+  if (typeof id !== "string" || !id) return null;
+  return id;
+}

extensions/msteams/src/messenger.test.ts

@@ -51,7 +51,7 @@ describe("msteams messenger", () => {
         [{ text: "hi", mediaUrl: "https://example.com/a.png" }],
         { textChunkLimit: 4000 },
       );
-      expect(messages).toEqual(["hi", "https://example.com/a.png"]);
+      expect(messages).toEqual([{ text: "hi" }, { mediaUrl: "https://example.com/a.png" }]);
     });
 
     it("supports inline media mode", () => {
@@ -59,7 +59,7 @@ describe("msteams messenger", () => {
         [{ text: "hi", mediaUrl: "https://example.com/a.png" }],
         { textChunkLimit: 4000, mediaMode: "inline" },
       );
-      expect(messages).toEqual(["hi\n\nhttps://example.com/a.png"]);
+      expect(messages).toEqual([{ text: "hi", mediaUrl: "https://example.com/a.png" }]);
     });
 
     it("chunks long text when enabled", () => {
@@ -101,7 +101,7 @@ describe("msteams messenger", () => {
         appId: "app123",
         conversationRef: baseRef,
         context: ctx,
-        messages: ["one", "two"],
+        messages: [{ text: "one" }, { text: "two" }],
       });
 
       expect(sent).toEqual(["one", "two"]);
@@ -129,7 +129,7 @@ describe("msteams messenger", () => {
         adapter,
         appId: "app123",
         conversationRef: baseRef,
-        messages: ["hello"],
+        messages: [{ text: "hello" }],
       });
 
       expect(seen.texts).toEqual(["hello"]);
@@ -168,7 +168,7 @@ describe("msteams messenger", () => {
         appId: "app123",
         conversationRef: baseRef,
         context: ctx,
-        messages: ["one"],
+        messages: [{ text: "one" }],
         retry: { maxAttempts: 2, baseDelayMs: 0, maxDelayMs: 0 },
         onRetry: (e) => retryEvents.push({ nextAttempt: e.nextAttempt, delayMs: e.delayMs }),
       });
@@ -196,7 +196,7 @@ describe("msteams messenger", () => {
           appId: "app123",
           conversationRef: baseRef,
           context: ctx,
-          messages: ["one"],
+          messages: [{ text: "one" }],
           retry: { maxAttempts: 3, baseDelayMs: 0, maxDelayMs: 0 },
         }),
       ).rejects.toMatchObject({ statusCode: 400 });
@@ -227,7 +227,7 @@ describe("msteams messenger", () => {
         adapter,
         appId: "app123",
         conversationRef: baseRef,
-        messages: ["hello"],
+        messages: [{ text: "hello" }],
         retry: { maxAttempts: 2, baseDelayMs: 0, maxDelayMs: 0 },
       });
 

extensions/msteams/src/messenger.ts

@@ -1,13 +1,35 @@
 import {
   isSilentReplyText,
+  loadWebMedia,
   type MSTeamsReplyStyle,
   type ReplyPayload,
   SILENT_REPLY_TOKEN,
 } from "clawdbot/plugin-sdk";
+import type { MSTeamsAccessTokenProvider } from "./attachments/types.js";
 import type { StoredConversationReference } from "./conversation-store.js";
 import { classifyMSTeamsSendError } from "./errors.js";
+import { prepareFileConsentActivity, requiresFileConsent } from "./file-consent-helpers.js";
+import { buildTeamsFileInfoCard } from "./graph-chat.js";
+import {
+  getDriveItemProperties,
+  uploadAndShareOneDrive,
+  uploadAndShareSharePoint,
+} from "./graph-upload.js";
+import { extractFilename, extractMessageId, getMimeType, isLocalPath } from "./media-helpers.js";
 import { getMSTeamsRuntime } from "./runtime.js";
 
+/**
+ * MSTeams-specific media size limit (100MB).
+ * Higher than the default because OneDrive upload handles large files well.
+ */
+const MSTEAMS_MAX_MEDIA_BYTES = 100 * 1024 * 1024;
+
+/**
+ * Threshold for large files that require FileConsentCard flow in personal chats.
+ * Files >= 4MB use consent flow; smaller images can use inline base64.
+ */
+const FILE_CONSENT_THRESHOLD_BYTES = 4 * 1024 * 1024;
+
 type SendContext = {
   sendActivity: (textOrActivity: string | object) => Promise<unknown>;
 };
@@ -41,6 +63,15 @@ export type MSTeamsReplyRenderOptions = {
   mediaMode?: "split" | "inline";
 };
 
+/**
+ * A rendered message that preserves media vs text distinction.
+ * When mediaUrl is present, it will be sent as a Bot Framework attachment.
+ */
+export type MSTeamsRenderedMessage = {
+  text?: string;
+  mediaUrl?: string;
+};
+
 export type MSTeamsSendRetryOptions = {
   maxAttempts?: number;
   baseDelayMs?: number;
@@ -90,16 +121,8 @@ export function buildConversationReference(
   };
 }
 
-function extractMessageId(response: unknown): string | null {
-  if (!response || typeof response !== "object") return null;
-  if (!("id" in response)) return null;
-  const { id } = response as { id?: unknown };
-  if (typeof id !== "string" || !id) return null;
-  return id;
-}
-
 function pushTextMessages(
-  out: string[],
+  out: MSTeamsRenderedMessage[],
   text: string,
   opts: {
     chunkText: boolean;
@@ -111,16 +134,17 @@ function pushTextMessages(
     for (const chunk of getMSTeamsRuntime().channel.text.chunkMarkdownText(text, opts.chunkLimit)) {
       const trimmed = chunk.trim();
       if (!trimmed || isSilentReplyText(trimmed, SILENT_REPLY_TOKEN)) continue;
-      out.push(trimmed);
+      out.push({ text: trimmed });
     }
     return;
   }
 
   const trimmed = text.trim();
   if (!trimmed || isSilentReplyText(trimmed, SILENT_REPLY_TOKEN)) return;
-  out.push(trimmed);
+  out.push({ text: trimmed });
 }
 
+
 function clampMs(value: number, maxMs: number): number {
   if (!Number.isFinite(value) || value < 0) return 0;
   return Math.min(value, maxMs);
@@ -167,8 +191,8 @@ function shouldRetry(classification: ReturnType<typeof classifyMSTeamsSendError>
 export function renderReplyPayloadsToMessages(
   replies: ReplyPayload[],
   options: MSTeamsReplyRenderOptions,
-): string[] {
-  const out: string[] = [];
+): MSTeamsRenderedMessage[] {
+  const out: MSTeamsRenderedMessage[] = [];
   const chunkLimit = Math.min(options.textChunkLimit, 4000);
   const chunkText = options.chunkText !== false;
   const mediaMode = options.mediaMode ?? "split";
@@ -185,8 +209,17 @@ export function renderReplyPayloadsToMessages(
     }
 
     if (mediaMode === "inline") {
-      const combined = text ? `${text}\n\n${mediaList.join("\n")}` : mediaList.join("\n");
-      pushTextMessages(out, combined, { chunkText, chunkLimit });
+      // For inline mode, combine text with first media as attachment
+      const firstMedia = mediaList[0];
+      if (firstMedia) {
+        out.push({ text: text || undefined, mediaUrl: firstMedia });
+        // Additional media URLs as separate messages
+        for (let i = 1; i < mediaList.length; i++) {
+          if (mediaList[i]) out.push({ mediaUrl: mediaList[i] });
+        }
+      } else {
+        pushTextMessages(out, text, { chunkText, chunkLimit });
+      }
       continue;
     }
 
@@ -194,26 +227,142 @@ export function renderReplyPayloadsToMessages(
     pushTextMessages(out, text, { chunkText, chunkLimit });
     for (const mediaUrl of mediaList) {
       if (!mediaUrl) continue;
-      out.push(mediaUrl);
+      out.push({ mediaUrl });
     }
   }
 
   return out;
 }
 
+async function buildActivity(
+  msg: MSTeamsRenderedMessage,
+  conversationRef: StoredConversationReference,
+  tokenProvider?: MSTeamsAccessTokenProvider,
+  sharePointSiteId?: string,
+  mediaMaxBytes?: number,
+): Promise<Record<string, unknown>> {
+  const activity: Record<string, unknown> = { type: "message" };
+
+  if (msg.text) {
+    activity.text = msg.text;
+  }
+
+  if (msg.mediaUrl) {
+    let contentUrl = msg.mediaUrl;
+    let contentType = await getMimeType(msg.mediaUrl);
+    let fileName = await extractFilename(msg.mediaUrl);
+
+    if (isLocalPath(msg.mediaUrl)) {
+      const maxBytes = mediaMaxBytes ?? MSTEAMS_MAX_MEDIA_BYTES;
+      const media = await loadWebMedia(msg.mediaUrl, maxBytes);
+      contentType = media.contentType ?? contentType;
+      fileName = media.fileName ?? fileName;
+
+      // Determine conversation type and file type
+      // Teams only accepts base64 data URLs for images
+      const conversationType = conversationRef.conversation?.conversationType?.toLowerCase();
+      const isPersonal = conversationType === "personal";
+      const isImage = contentType?.startsWith("image/") ?? false;
+
+      if (requiresFileConsent({
+        conversationType,
+        contentType,
+        bufferSize: media.buffer.length,
+        thresholdBytes: FILE_CONSENT_THRESHOLD_BYTES,
+      })) {
+        // Large file or non-image in personal chat: use FileConsentCard flow
+        const conversationId = conversationRef.conversation?.id ?? "unknown";
+        const { activity: consentActivity } = prepareFileConsentActivity({
+          media: { buffer: media.buffer, filename: fileName, contentType },
+          conversationId,
+          description: msg.text || undefined,
+        });
+
+        // Return the consent activity (caller sends it)
+        return consentActivity;
+      }
+
+      if (!isPersonal && !isImage && tokenProvider && sharePointSiteId) {
+        // Non-image in group chat/channel with SharePoint site configured:
+        // Upload to SharePoint and use native file card attachment
+        const chatId = conversationRef.conversation?.id;
+
+        // Upload to SharePoint
+        const uploaded = await uploadAndShareSharePoint({
+          buffer: media.buffer,
+          filename: fileName,
+          contentType,
+          tokenProvider,
+          siteId: sharePointSiteId,
+          chatId: chatId ?? undefined,
+          usePerUserSharing: conversationType === "groupchat",
+        });
+
+        // Get driveItem properties needed for native file card attachment
+        const driveItem = await getDriveItemProperties({
+          siteId: sharePointSiteId,
+          itemId: uploaded.itemId,
+          tokenProvider,
+        });
+
+        // Build native Teams file card attachment
+        const fileCardAttachment = buildTeamsFileInfoCard(driveItem);
+        activity.attachments = [fileCardAttachment];
+
+        return activity;
+      }
+
+      if (!isPersonal && !isImage && tokenProvider) {
+        // Fallback: no SharePoint site configured, try OneDrive upload
+        const uploaded = await uploadAndShareOneDrive({
+          buffer: media.buffer,
+          filename: fileName,
+          contentType,
+          tokenProvider,
+        });
+
+        // Bot Framework doesn't support "reference" attachment type for sending
+        const fileLink = `📎 [${uploaded.name}](${uploaded.shareUrl})`;
+        activity.text = msg.text ? `${msg.text}\n\n${fileLink}` : fileLink;
+        return activity;
+      }
+
+      // Image (any chat): use base64 (works for images in all conversation types)
+      const base64 = media.buffer.toString("base64");
+      contentUrl = `data:${media.contentType};base64,${base64}`;
+    }
+
+    activity.attachments = [
+      {
+        name: fileName,
+        contentType,
+        contentUrl,
+      },
+    ];
+  }
+
+  return activity;
+}
+
 export async function sendMSTeamsMessages(params: {
   replyStyle: MSTeamsReplyStyle;
   adapter: MSTeamsAdapter;
   appId: string;
   conversationRef: StoredConversationReference;
   context?: SendContext;
-  messages: string[];
+  messages: MSTeamsRenderedMessage[];
   retry?: false | MSTeamsSendRetryOptions;
   onRetry?: (event: MSTeamsSendRetryEvent) => void;
+  /** Token provider for OneDrive/SharePoint uploads in group chats/channels */
+  tokenProvider?: MSTeamsAccessTokenProvider;
+  /** SharePoint site ID for file uploads in group chats/channels */
+  sharePointSiteId?: string;
+  /** Max media size in bytes. Default: 100MB. */
+  mediaMaxBytes?: number;
 }): Promise<string[]> {
-  const messages = params.messages
-    .map((m) => (typeof m === "string" ? m : String(m)))
-    .filter((m) => m.trim().length > 0);
+  const messages = params.messages.filter(
+    (m) => (m.text && m.text.trim().length > 0) || m.mediaUrl,
+  );
   if (messages.length === 0) return [];
 
   const retryOptions = resolveRetryOptions(params.retry);
@@ -259,10 +408,9 @@ export async function sendMSTeamsMessages(params: {
     for (const [idx, message] of messages.entries()) {
       const response = await sendWithRetry(
         async () =>
-          await ctx.sendActivity({
-            type: "message",
-            text: message,
-          }),
+          await ctx.sendActivity(
+            await buildActivity(message, params.conversationRef, params.tokenProvider, params.sharePointSiteId, params.mediaMaxBytes),
+          ),
         { messageIndex: idx, messageCount: messages.length },
       );
       messageIds.push(extractMessageId(response) ?? "unknown");
@@ -281,10 +429,9 @@ export async function sendMSTeamsMessages(params: {
     for (const [idx, message] of messages.entries()) {
       const response = await sendWithRetry(
         async () =>
-          await ctx.sendActivity({
-            type: "message",
-            text: message,
-          }),
+          await ctx.sendActivity(
+            await buildActivity(message, params.conversationRef, params.tokenProvider, params.sharePointSiteId, params.mediaMaxBytes),
+          ),
         { messageIndex: idx, messageCount: messages.length },
       );
       messageIds.push(extractMessageId(response) ?? "unknown");

extensions/msteams/src/monitor-handler.ts

@@ -1,8 +1,14 @@
 import type { ClawdbotConfig, RuntimeEnv } from "clawdbot/plugin-sdk";
 import type { MSTeamsConversationStore } from "./conversation-store.js";
+import {
+  buildFileInfoCard,
+  parseFileConsentInvoke,
+  uploadToConsentUrl,
+} from "./file-consent.js";
 import type { MSTeamsAdapter } from "./messenger.js";
 import { createMSTeamsMessageHandler } from "./monitor-handler/message-handler.js";
 import type { MSTeamsMonitorLogger } from "./monitor-types.js";
+import { getPendingUpload, removePendingUpload } from "./pending-uploads.js";
 import type { MSTeamsPollStore } from "./polls.js";
 import type { MSTeamsTurnContext } from "./sdk-types.js";
 
@@ -17,6 +23,7 @@ export type MSTeamsActivityHandler = {
   onMembersAdded: (
     handler: (context: unknown, next: () => Promise<void>) => Promise<void>,
   ) => MSTeamsActivityHandler;
+  run?: (context: unknown) => Promise<void>;
 };
 
 export type MSTeamsMessageHandlerDeps = {
@@ -32,11 +39,109 @@ export type MSTeamsMessageHandlerDeps = {
   log: MSTeamsMonitorLogger;
 };
 
+/**
+ * Handle fileConsent/invoke activities for large file uploads.
+ */
+async function handleFileConsentInvoke(
+  context: MSTeamsTurnContext,
+  log: MSTeamsMonitorLogger,
+): Promise<boolean> {
+  const activity = context.activity;
+  if (activity.type !== "invoke" || activity.name !== "fileConsent/invoke") {
+    return false;
+  }
+
+  const consentResponse = parseFileConsentInvoke(activity);
+  if (!consentResponse) {
+    log.debug("invalid file consent invoke", { value: activity.value });
+    return false;
+  }
+
+  const uploadId =
+    typeof consentResponse.context?.uploadId === "string"
+      ? consentResponse.context.uploadId
+      : undefined;
+
+  if (consentResponse.action === "accept" && consentResponse.uploadInfo) {
+    const pendingFile = getPendingUpload(uploadId);
+    if (pendingFile) {
+      log.debug("user accepted file consent, uploading", {
+        uploadId,
+        filename: pendingFile.filename,
+        size: pendingFile.buffer.length,
+      });
+
+      try {
+        // Upload file to the provided URL
+        await uploadToConsentUrl({
+          url: consentResponse.uploadInfo.uploadUrl,
+          buffer: pendingFile.buffer,
+          contentType: pendingFile.contentType,
+        });
+
+        // Send confirmation card
+        const fileInfoCard = buildFileInfoCard({
+          filename: consentResponse.uploadInfo.name,
+          contentUrl: consentResponse.uploadInfo.contentUrl,
+          uniqueId: consentResponse.uploadInfo.uniqueId,
+          fileType: consentResponse.uploadInfo.fileType,
+        });
+
+        await context.sendActivity({
+          type: "message",
+          attachments: [fileInfoCard],
+        });
+
+        log.info("file upload complete", {
+          uploadId,
+          filename: consentResponse.uploadInfo.name,
+          uniqueId: consentResponse.uploadInfo.uniqueId,
+        });
+      } catch (err) {
+        log.debug("file upload failed", { uploadId, error: String(err) });
+        await context.sendActivity(`File upload failed: ${String(err)}`);
+      } finally {
+        removePendingUpload(uploadId);
+      }
+    } else {
+      log.debug("pending file not found for consent", { uploadId });
+      await context.sendActivity(
+        "The file upload request has expired. Please try sending the file again.",
+      );
+    }
+  } else {
+    // User declined
+    log.debug("user declined file consent", { uploadId });
+    removePendingUpload(uploadId);
+  }
+
+  return true;
+}
+
 export function registerMSTeamsHandlers<T extends MSTeamsActivityHandler>(
   handler: T,
   deps: MSTeamsMessageHandlerDeps,
 ): T {
   const handleTeamsMessage = createMSTeamsMessageHandler(deps);
+
+  // Wrap the original run method to intercept invokes
+  const originalRun = handler.run;
+  if (originalRun) {
+    handler.run = async (context: unknown) => {
+      const ctx = context as MSTeamsTurnContext;
+      // Handle file consent invokes before passing to normal flow
+      if (ctx.activity?.type === "invoke" && ctx.activity?.name === "fileConsent/invoke") {
+        const handled = await handleFileConsentInvoke(ctx, deps.log);
+        if (handled) {
+          // Send invoke response for file consent
+          await ctx.sendActivity({ type: "invokeResponse", value: { status: 200 } });
+          return;
+        }
+      }
+      return originalRun.call(handler, context);
+    };
+  }
+
   handler.onMessage(async (context, next) => {
     try {
       await handleTeamsMessage(context as MSTeamsTurnContext);

extensions/msteams/src/monitor-handler/inbound-media.ts

@@ -1,7 +1,7 @@
 import {
   buildMSTeamsGraphMessageUrls,
+  downloadMSTeamsAttachments,
   downloadMSTeamsGraphMedia,
-  downloadMSTeamsImageAttachments,
   type MSTeamsAccessTokenProvider,
   type MSTeamsAttachmentLike,
   type MSTeamsHtmlAttachmentSummary,
@@ -24,6 +24,8 @@ export async function resolveMSTeamsInboundMedia(params: {
   conversationMessageId?: string;
   activity: Pick<MSTeamsTurnContext["activity"], "id" | "replyToId" | "channelData">;
   log: MSTeamsLogger;
+  /** When true, embeds original filename in stored path for later extraction. */
+  preserveFilenames?: boolean;
 }): Promise<MSTeamsInboundMedia[]> {
   const {
     attachments,
@@ -36,13 +38,15 @@ export async function resolveMSTeamsInboundMedia(params: {
     conversationMessageId,
     activity,
     log,
+    preserveFilenames,
   } = params;
 
-  let mediaList = await downloadMSTeamsImageAttachments({
+  let mediaList = await downloadMSTeamsAttachments({
     attachments,
     maxBytes,
     tokenProvider,
     allowHosts,
+    preserveFilenames,
   });
 
   if (mediaList.length === 0) {
@@ -81,6 +85,7 @@ export async function resolveMSTeamsInboundMedia(params: {
             tokenProvider,
             maxBytes,
             allowHosts,
+            preserveFilenames,
           });
           attempts.push({
             url: messageUrl,
@@ -104,7 +109,7 @@ export async function resolveMSTeamsInboundMedia(params: {
   }
 
   if (mediaList.length > 0) {
-    log.debug("downloaded image attachments", { count: mediaList.length });
+    log.debug("downloaded attachments", { count: mediaList.length });
   } else if (htmlSummary?.imgTags) {
     log.debug("inline images detected but none downloaded", {
       imgTags: htmlSummary.imgTags,

extensions/msteams/src/monitor-handler/message-handler.ts

@@ -402,7 +402,8 @@ export function createMSTeamsMessageHandler(deps: MSTeamsMessageHandlerDeps) {
         channelData: activity.channelData,
       },
       log,
-	    });
+      preserveFilenames: cfg.media?.preserveFilenames,
+    });
 
 	    const mediaPayload = buildMSTeamsMediaPayload(mediaList);
 	    const envelopeFrom = isDirectMessage ? senderName : conversationType;
@@ -476,6 +477,7 @@ export function createMSTeamsMessageHandler(deps: MSTeamsMessageHandlerDeps) {
 
     logVerboseMessage(`msteams inbound: from=${ctxPayload.From} preview="${preview}"`);
 
+    const sharePointSiteId = msteamsCfg?.sharePointSiteId;
     const { dispatcher, replyOptions, markDispatchIdle } = createMSTeamsReplyDispatcher({
       cfg,
       agentId: route.agentId,
@@ -492,6 +494,8 @@ export function createMSTeamsMessageHandler(deps: MSTeamsMessageHandlerDeps) {
           recordMSTeamsSentMessage(conversationId, id);
         }
       },
+      tokenProvider,
+      sharePointSiteId,
     });
 
     log.info("dispatching to agent", { sessionKey: route.sessionKey });

extensions/msteams/src/pending-uploads.ts

@@ -0,0 +1,87 @@
+/**
+ * In-memory storage for files awaiting user consent in the FileConsentCard flow.
+ *
+ * When sending large files (>=4MB) in personal chats, Teams requires user consent
+ * before upload. This module stores the file data temporarily until the user
+ * accepts or declines, or until the TTL expires.
+ */
+
+import crypto from "node:crypto";
+
+export interface PendingUpload {
+  id: string;
+  buffer: Buffer;
+  filename: string;
+  contentType?: string;
+  conversationId: string;
+  createdAt: number;
+}
+
+const pendingUploads = new Map<string, PendingUpload>();
+
+/** TTL for pending uploads: 5 minutes */
+const PENDING_UPLOAD_TTL_MS = 5 * 60 * 1000;
+
+/**
+ * Store a file pending user consent.
+ * Returns the upload ID to include in the FileConsentCard context.
+ */
+export function storePendingUpload(
+  upload: Omit<PendingUpload, "id" | "createdAt">,
+): string {
+  const id = crypto.randomUUID();
+  const entry: PendingUpload = {
+    ...upload,
+    id,
+    createdAt: Date.now(),
+  };
+  pendingUploads.set(id, entry);
+
+  // Auto-cleanup after TTL
+  setTimeout(() => {
+    pendingUploads.delete(id);
+  }, PENDING_UPLOAD_TTL_MS);
+
+  return id;
+}
+
+/**
+ * Retrieve a pending upload by ID.
+ * Returns undefined if not found or expired.
+ */
+export function getPendingUpload(id?: string): PendingUpload | undefined {
+  if (!id) return undefined;
+  const entry = pendingUploads.get(id);
+  if (!entry) return undefined;
+
+  // Check if expired (in case timeout hasn't fired yet)
+  if (Date.now() - entry.createdAt > PENDING_UPLOAD_TTL_MS) {
+    pendingUploads.delete(id);
+    return undefined;
+  }
+
+  return entry;
+}
+
+/**
+ * Remove a pending upload (after successful upload or user decline).
+ */
+export function removePendingUpload(id?: string): void {
+  if (id) {
+    pendingUploads.delete(id);
+  }
+}
+
+/**
+ * Get the count of pending uploads (for monitoring/debugging).
+ */
+export function getPendingUploadCount(): number {
+  return pendingUploads.size;
+}
+
+/**
+ * Clear all pending uploads (for testing).
+ */
+export function clearPendingUploads(): void {
+  pendingUploads.clear();
+}

extensions/msteams/src/probe.ts

@@ -76,7 +76,7 @@ export async function probeMSTeams(cfg?: MSTeamsConfig): Promise<ProbeMSTeamsRes
       | undefined;
     try {
       const graphToken = await tokenProvider.getAccessToken(
-        "https://graph.microsoft.com/.default",
+        "https://graph.microsoft.com",
       );
       const accessToken = readAccessToken(graphToken);
       const payload = accessToken ? decodeJwtPayload(accessToken) : null;

extensions/msteams/src/reply-dispatcher.ts

@@ -1,8 +1,10 @@
-import type {
-  ClawdbotConfig,
-  MSTeamsReplyStyle,
-  RuntimeEnv,
+import {
+  resolveChannelMediaMaxBytes,
+  type ClawdbotConfig,
+  type MSTeamsReplyStyle,
+  type RuntimeEnv,
 } from "clawdbot/plugin-sdk";
+import type { MSTeamsAccessTokenProvider } from "./attachments/types.js";
 import type { StoredConversationReference } from "./conversation-store.js";
 import {
   classifyMSTeamsSendError,
@@ -30,6 +32,10 @@ export function createMSTeamsReplyDispatcher(params: {
   replyStyle: MSTeamsReplyStyle;
   textLimit: number;
   onSentMessageIds?: (ids: string[]) => void;
+  /** Token provider for OneDrive/SharePoint uploads in group chats/channels */
+  tokenProvider?: MSTeamsAccessTokenProvider;
+  /** SharePoint site ID for file uploads in group chats/channels */
+  sharePointSiteId?: string;
 }) {
   const core = getMSTeamsRuntime();
   const sendTypingIndicator = async () => {
@@ -52,6 +58,10 @@ export function createMSTeamsReplyDispatcher(params: {
         chunkText: true,
         mediaMode: "split",
       });
+      const mediaMaxBytes = resolveChannelMediaMaxBytes({
+        cfg: params.cfg,
+        resolveChannelLimitMb: ({ cfg }) => cfg.channels?.msteams?.mediaMaxMb,
+      });
       const ids = await sendMSTeamsMessages({
         replyStyle: params.replyStyle,
         adapter: params.adapter,
@@ -67,6 +77,9 @@ export function createMSTeamsReplyDispatcher(params: {
             ...event,
           });
         },
+        tokenProvider: params.tokenProvider,
+        sharePointSiteId: params.sharePointSiteId,
+        mediaMaxBytes,
       });
       if (ids.length > 0) params.onSentMessageIds?.(ids);
     },

extensions/msteams/src/send-context.ts

@@ -1,29 +1,31 @@
-import type { ClawdbotConfig, PluginRuntime } from "clawdbot/plugin-sdk";
+import { resolveChannelMediaMaxBytes, type ClawdbotConfig, type PluginRuntime } from "clawdbot/plugin-sdk";
+import type { MSTeamsAccessTokenProvider } from "./attachments/types.js";
 import type {
   MSTeamsConversationStore,
   StoredConversationReference,
 } from "./conversation-store.js";
 import { createMSTeamsConversationStoreFs } from "./conversation-store-fs.js";
 import type { MSTeamsAdapter } from "./messenger.js";
+import { getMSTeamsRuntime } from "./runtime.js";
 import { createMSTeamsAdapter, loadMSTeamsSdkWithAuth } from "./sdk.js";
 import { resolveMSTeamsCredentials } from "./token.js";
 
-type GetChildLogger = PluginRuntime["logging"]["getChildLogger"];
-
-let _log: ReturnType<GetChildLogger> | undefined;
-const getLog = async (): Promise<ReturnType<GetChildLogger>> => {
-  if (_log) return _log;
-  const { getChildLogger } = await import("../logging.js");
-  _log = getChildLogger({ name: "msteams:send" });
-  return _log;
-};
+export type MSTeamsConversationType = "personal" | "groupChat" | "channel";
 
 export type MSTeamsProactiveContext = {
   appId: string;
   conversationId: string;
   ref: StoredConversationReference;
   adapter: MSTeamsAdapter;
-  log: Awaited<ReturnType<typeof getLog>>;
+  log: ReturnType<PluginRuntime["logging"]["getChildLogger"]>;
+  /** The type of conversation: personal (1:1), groupChat, or channel */
+  conversationType: MSTeamsConversationType;
+  /** Token provider for Graph API / OneDrive operations */
+  tokenProvider: MSTeamsAccessTokenProvider;
+  /** SharePoint site ID for file uploads in group chats/channels */
+  sharePointSiteId?: string;
+  /** Resolved media max bytes from config (default: 100MB) */
+  mediaMaxBytes?: number;
 };
 
 /**
@@ -110,16 +112,45 @@ export async function resolveMSTeamsSendContext(params: {
   }
 
   const { conversationId, ref } = found;
-  const log = await getLog();
+  const core = getMSTeamsRuntime();
+  const log = core.logging.getChildLogger({ name: "msteams:send" });
 
   const { sdk, authConfig } = await loadMSTeamsSdkWithAuth(creds);
   const adapter = createMSTeamsAdapter(authConfig, sdk);
 
+  // Create token provider for Graph API / OneDrive operations
+  const tokenProvider = new sdk.MsalTokenProvider(authConfig) as MSTeamsAccessTokenProvider;
+
+  // Determine conversation type from stored reference
+  const storedConversationType = ref.conversation?.conversationType?.toLowerCase() ?? "";
+  let conversationType: MSTeamsConversationType;
+  if (storedConversationType === "personal") {
+    conversationType = "personal";
+  } else if (storedConversationType === "channel") {
+    conversationType = "channel";
+  } else {
+    // groupChat, or unknown defaults to groupChat behavior
+    conversationType = "groupChat";
+  }
+
+  // Get SharePoint site ID from config (required for file uploads in group chats/channels)
+  const sharePointSiteId = msteamsCfg.sharePointSiteId;
+
+  // Resolve media max bytes from config
+  const mediaMaxBytes = resolveChannelMediaMaxBytes({
+    cfg: params.cfg,
+    resolveChannelLimitMb: ({ cfg }) => cfg.channels?.msteams?.mediaMaxMb,
+  });
+
   return {
     appId: creds.appId,
     conversationId,
     ref,
     adapter: adapter as unknown as MSTeamsAdapter,
     log,
+    conversationType,
+    tokenProvider,
+    sharePointSiteId,
+    mediaMaxBytes,
   };
 }

extensions/msteams/src/send.ts

@@ -1,18 +1,22 @@
+import { loadWebMedia, resolveChannelMediaMaxBytes } from "clawdbot/plugin-sdk";
 import type { ClawdbotConfig } from "clawdbot/plugin-sdk";
-import type { StoredConversationReference } from "./conversation-store.js";
 import { createMSTeamsConversationStoreFs } from "./conversation-store-fs.js";
 import {
   classifyMSTeamsSendError,
   formatMSTeamsSendErrorHint,
   formatUnknownError,
 } from "./errors.js";
+import { prepareFileConsentActivity, requiresFileConsent } from "./file-consent-helpers.js";
+import { buildTeamsFileInfoCard } from "./graph-chat.js";
 import {
-  buildConversationReference,
-  type MSTeamsAdapter,
-  sendMSTeamsMessages,
-} from "./messenger.js";
+  getDriveItemProperties,
+  uploadAndShareOneDrive,
+  uploadAndShareSharePoint,
+} from "./graph-upload.js";
+import { extractFilename, extractMessageId } from "./media-helpers.js";
+import { buildConversationReference, sendMSTeamsMessages } from "./messenger.js";
 import { buildMSTeamsPollCard } from "./polls.js";
-import { resolveMSTeamsSendContext } from "./send-context.js";
+import { resolveMSTeamsSendContext, type MSTeamsProactiveContext } from "./send-context.js";
 
 export type SendMSTeamsMessageParams = {
   /** Full config (for credentials) */
@@ -28,8 +32,19 @@ export type SendMSTeamsMessageParams = {
 export type SendMSTeamsMessageResult = {
   messageId: string;
   conversationId: string;
+  /** If a FileConsentCard was sent instead of the file, this contains the upload ID */
+  pendingUploadId?: string;
 };
 
+/** Threshold for large files that require FileConsentCard flow in personal chats */
+const FILE_CONSENT_THRESHOLD_BYTES = 4 * 1024 * 1024; // 4MB
+
+/**
+ * MSTeams-specific media size limit (100MB).
+ * Higher than the default because OneDrive upload handles large files well.
+ */
+const MSTEAMS_MAX_MEDIA_BYTES = 100 * 1024 * 1024;
+
 export type SendMSTeamsPollParams = {
   /** Full config (for credentials) */
   cfg: ClawdbotConfig;
@@ -49,32 +64,19 @@ export type SendMSTeamsPollResult = {
   conversationId: string;
 };
 
-function extractMessageId(response: unknown): string | null {
-  if (!response || typeof response !== "object") return null;
-  if (!("id" in response)) return null;
-  const { id } = response as { id?: unknown };
-  if (typeof id !== "string" || !id) return null;
-  return id;
-}
+export type SendMSTeamsCardParams = {
+  /** Full config (for credentials) */
+  cfg: ClawdbotConfig;
+  /** Conversation ID or user ID to send to */
+  to: string;
+  /** Adaptive Card JSON object */
+  card: Record<string, unknown>;
+};
 
-async function sendMSTeamsActivity(params: {
-  adapter: MSTeamsAdapter;
-  appId: string;
-  conversationRef: StoredConversationReference;
-  activity: Record<string, unknown>;
-}): Promise<string> {
-  const baseRef = buildConversationReference(params.conversationRef);
-  const proactiveRef = {
-    ...baseRef,
-    activityId: undefined,
-  };
-  let messageId = "unknown";
-  await params.adapter.continueConversation(params.appId, proactiveRef, async (ctx) => {
-    const response = await ctx.sendActivity(params.activity);
-    messageId = extractMessageId(response) ?? "unknown";
-  });
-  return messageId;
-}
+export type SendMSTeamsCardResult = {
+  messageId: string;
+  conversationId: string;
+};
 
 /**
  * Send a message to a Teams conversation or user.
@@ -82,23 +84,225 @@ async function sendMSTeamsActivity(params: {
  * Uses the stored ConversationReference from previous interactions.
  * The bot must have received at least one message from the conversation
  * before proactive messaging works.
+ *
+ * File handling by conversation type:
+ * - Personal (1:1) chats: small images (<4MB) use base64, large files and non-images use FileConsentCard
+ * - Group chats / channels: files are uploaded to OneDrive and shared via link
  */
 export async function sendMessageMSTeams(
   params: SendMSTeamsMessageParams,
 ): Promise<SendMSTeamsMessageResult> {
   const { cfg, to, text, mediaUrl } = params;
-  const { adapter, appId, conversationId, ref, log } = await resolveMSTeamsSendContext({
-    cfg,
-    to,
-  });
+  const ctx = await resolveMSTeamsSendContext({ cfg, to });
+  const { adapter, appId, conversationId, ref, log, conversationType, tokenProvider, sharePointSiteId } = ctx;
 
   log.debug("sending proactive message", {
     conversationId,
+    conversationType,
     textLength: text.length,
     hasMedia: Boolean(mediaUrl),
   });
 
-  const message = mediaUrl ? (text ? `${text}\n\n${mediaUrl}` : mediaUrl) : text;
+  // Handle media if present
+  if (mediaUrl) {
+    const mediaMaxBytes = resolveChannelMediaMaxBytes({
+      cfg,
+      resolveChannelLimitMb: ({ cfg }) => cfg.channels?.msteams?.mediaMaxMb,
+    }) ?? MSTEAMS_MAX_MEDIA_BYTES;
+    const media = await loadWebMedia(mediaUrl, mediaMaxBytes);
+    const isLargeFile = media.buffer.length >= FILE_CONSENT_THRESHOLD_BYTES;
+    const isImage = media.contentType?.startsWith("image/") ?? false;
+    const fallbackFileName = await extractFilename(mediaUrl);
+    const fileName = media.fileName ?? fallbackFileName;
+
+    log.debug("processing media", {
+      fileName,
+      contentType: media.contentType,
+      size: media.buffer.length,
+      isLargeFile,
+      isImage,
+      conversationType,
+    });
+
+    // Personal chats: base64 only works for images; use FileConsentCard for large files or non-images
+    if (requiresFileConsent({
+      conversationType,
+      contentType: media.contentType,
+      bufferSize: media.buffer.length,
+      thresholdBytes: FILE_CONSENT_THRESHOLD_BYTES,
+    })) {
+      const { activity, uploadId } = prepareFileConsentActivity({
+        media: { buffer: media.buffer, filename: fileName, contentType: media.contentType },
+        conversationId,
+        description: text || undefined,
+      });
+
+      log.debug("sending file consent card", { uploadId, fileName, size: media.buffer.length });
+
+      const baseRef = buildConversationReference(ref);
+      const proactiveRef = { ...baseRef, activityId: undefined };
+
+      let messageId = "unknown";
+      try {
+        await adapter.continueConversation(appId, proactiveRef, async (turnCtx) => {
+          const response = await turnCtx.sendActivity(activity);
+          messageId = extractMessageId(response) ?? "unknown";
+        });
+      } catch (err) {
+        const classification = classifyMSTeamsSendError(err);
+        const hint = formatMSTeamsSendErrorHint(classification);
+        const status = classification.statusCode ? ` (HTTP ${classification.statusCode})` : "";
+        throw new Error(
+          `msteams consent card send failed${status}: ${formatUnknownError(err)}${hint ? ` (${hint})` : ""}`,
+        );
+      }
+
+      log.info("sent file consent card", { conversationId, messageId, uploadId });
+
+      return {
+        messageId,
+        conversationId,
+        pendingUploadId: uploadId,
+      };
+    }
+
+    // Personal chat with small image: use base64 (only works for images)
+    if (conversationType === "personal") {
+      // Small image in personal chat: use base64 (only works for images)
+      const base64 = media.buffer.toString("base64");
+      const finalMediaUrl = `data:${media.contentType};base64,${base64}`;
+
+      return sendTextWithMedia(ctx, text, finalMediaUrl);
+    }
+
+    if (isImage && !sharePointSiteId) {
+      // Group chat/channel without SharePoint: send image inline (avoids OneDrive failures)
+      const base64 = media.buffer.toString("base64");
+      const finalMediaUrl = `data:${media.contentType};base64,${base64}`;
+      return sendTextWithMedia(ctx, text, finalMediaUrl);
+    }
+
+    // Group chat or channel: upload to SharePoint (if siteId configured) or OneDrive
+    try {
+      if (sharePointSiteId) {
+        // Use SharePoint upload + Graph API for native file card
+        log.debug("uploading to SharePoint for native file card", {
+          fileName,
+          conversationType,
+          siteId: sharePointSiteId,
+        });
+
+        const uploaded = await uploadAndShareSharePoint({
+          buffer: media.buffer,
+          filename: fileName,
+          contentType: media.contentType,
+          tokenProvider,
+          siteId: sharePointSiteId,
+          chatId: conversationId,
+          usePerUserSharing: conversationType === "groupChat",
+        });
+
+        log.debug("SharePoint upload complete", {
+          itemId: uploaded.itemId,
+          shareUrl: uploaded.shareUrl,
+        });
+
+        // Get driveItem properties needed for native file card
+        const driveItem = await getDriveItemProperties({
+          siteId: sharePointSiteId,
+          itemId: uploaded.itemId,
+          tokenProvider,
+        });
+
+        log.debug("driveItem properties retrieved", {
+          eTag: driveItem.eTag,
+          webDavUrl: driveItem.webDavUrl,
+        });
+
+        // Build native Teams file card attachment and send via Bot Framework
+        const fileCardAttachment = buildTeamsFileInfoCard(driveItem);
+        const activity = {
+          type: "message",
+          text: text || undefined,
+          attachments: [fileCardAttachment],
+        };
+
+        const baseRef = buildConversationReference(ref);
+        const proactiveRef = { ...baseRef, activityId: undefined };
+
+        let messageId = "unknown";
+        await adapter.continueConversation(appId, proactiveRef, async (turnCtx) => {
+          const response = await turnCtx.sendActivity(activity);
+          messageId = extractMessageId(response) ?? "unknown";
+        });
+
+        log.info("sent native file card", {
+          conversationId,
+          messageId,
+          fileName: driveItem.name,
+        });
+
+        return { messageId, conversationId };
+      }
+
+      // Fallback: no SharePoint site configured, use OneDrive with markdown link
+      log.debug("uploading to OneDrive (no SharePoint site configured)", { fileName, conversationType });
+
+      const uploaded = await uploadAndShareOneDrive({
+        buffer: media.buffer,
+        filename: fileName,
+        contentType: media.contentType,
+        tokenProvider,
+      });
+
+      log.debug("OneDrive upload complete", {
+        itemId: uploaded.itemId,
+        shareUrl: uploaded.shareUrl,
+      });
+
+      // Send message with file link (Bot Framework doesn't support "reference" attachment type for sending)
+      const fileLink = `📎 [${uploaded.name}](${uploaded.shareUrl})`;
+      const activity = {
+        type: "message",
+        text: text ? `${text}\n\n${fileLink}` : fileLink,
+      };
+
+      const baseRef = buildConversationReference(ref);
+      const proactiveRef = { ...baseRef, activityId: undefined };
+
+      let messageId = "unknown";
+      await adapter.continueConversation(appId, proactiveRef, async (turnCtx) => {
+        const response = await turnCtx.sendActivity(activity);
+        messageId = extractMessageId(response) ?? "unknown";
+      });
+
+      log.info("sent message with OneDrive file link", { conversationId, messageId, shareUrl: uploaded.shareUrl });
+
+      return { messageId, conversationId };
+    } catch (err) {
+      const classification = classifyMSTeamsSendError(err);
+      const hint = formatMSTeamsSendErrorHint(classification);
+      const status = classification.statusCode ? ` (HTTP ${classification.statusCode})` : "";
+      throw new Error(
+        `msteams file send failed${status}: ${formatUnknownError(err)}${hint ? ` (${hint})` : ""}`,
+      );
+    }
+  }
+
+  // No media: send text only
+  return sendTextWithMedia(ctx, text, undefined);
+}
+
+/**
+ * Send a text message with optional base64 media URL.
+ */
+async function sendTextWithMedia(
+  ctx: MSTeamsProactiveContext,
+  text: string,
+  mediaUrl: string | undefined,
+): Promise<SendMSTeamsMessageResult> {
+  const { adapter, appId, conversationId, ref, log, tokenProvider, sharePointSiteId, mediaMaxBytes } = ctx;
+
   let messageIds: string[];
   try {
     messageIds = await sendMSTeamsMessages({
@@ -106,12 +310,14 @@ export async function sendMessageMSTeams(
       adapter,
       appId,
       conversationRef: ref,
-      messages: [message],
-      // Enable default retry/backoff for throttling/transient failures.
+      messages: [{ text: text || undefined, mediaUrl }],
       retry: {},
       onRetry: (event) => {
         log.debug("retrying send", { conversationId, ...event });
       },
+      tokenProvider,
+      sharePointSiteId,
+      mediaMaxBytes,
     });
   } catch (err) {
     const classification = classifyMSTeamsSendError(err);
@@ -121,8 +327,8 @@ export async function sendMessageMSTeams(
       `msteams send failed${status}: ${formatUnknownError(err)}${hint ? ` (${hint})` : ""}`,
     );
   }
-  const messageId = messageIds[0] ?? "unknown";
 
+  const messageId = messageIds[0] ?? "unknown";
   log.info("sent proactive message", { conversationId, messageId });
 
   return {
@@ -157,7 +363,6 @@ export async function sendPollMSTeams(
 
   const activity = {
     type: "message",
-    text: pollCard.fallbackText,
     attachments: [
       {
         contentType: "application/vnd.microsoft.card.adaptive",
@@ -166,13 +371,18 @@ export async function sendPollMSTeams(
     ],
   };
 
-  let messageId: string;
+  // Send poll via proactive conversation (Adaptive Cards require direct activity send)
+  const baseRef = buildConversationReference(ref);
+  const proactiveRef = {
+    ...baseRef,
+    activityId: undefined,
+  };
+
+  let messageId = "unknown";
   try {
-    messageId = await sendMSTeamsActivity({
-      adapter,
-      appId,
-      conversationRef: ref,
-      activity,
+    await adapter.continueConversation(appId, proactiveRef, async (ctx) => {
+      const response = await ctx.sendActivity(activity);
+      messageId = extractMessageId(response) ?? "unknown";
     });
   } catch (err) {
     const classification = classifyMSTeamsSendError(err);
@@ -192,6 +402,64 @@ export async function sendPollMSTeams(
   };
 }
 
+/**
+ * Send an arbitrary Adaptive Card to a Teams conversation or user.
+ */
+export async function sendAdaptiveCardMSTeams(
+  params: SendMSTeamsCardParams,
+): Promise<SendMSTeamsCardResult> {
+  const { cfg, to, card } = params;
+  const { adapter, appId, conversationId, ref, log } = await resolveMSTeamsSendContext({
+    cfg,
+    to,
+  });
+
+  log.debug("sending adaptive card", {
+    conversationId,
+    cardType: card.type,
+    cardVersion: card.version,
+  });
+
+  const activity = {
+    type: "message",
+    attachments: [
+      {
+        contentType: "application/vnd.microsoft.card.adaptive",
+        content: card,
+      },
+    ],
+  };
+
+  // Send card via proactive conversation
+  const baseRef = buildConversationReference(ref);
+  const proactiveRef = {
+    ...baseRef,
+    activityId: undefined,
+  };
+
+  let messageId = "unknown";
+  try {
+    await adapter.continueConversation(appId, proactiveRef, async (ctx) => {
+      const response = await ctx.sendActivity(activity);
+      messageId = extractMessageId(response) ?? "unknown";
+    });
+  } catch (err) {
+    const classification = classifyMSTeamsSendError(err);
+    const hint = formatMSTeamsSendErrorHint(classification);
+    const status = classification.statusCode ? ` (HTTP ${classification.statusCode})` : "";
+    throw new Error(
+      `msteams card send failed${status}: ${formatUnknownError(err)}${hint ? ` (${hint})` : ""}`,
+    );
+  }
+
+  log.info("sent adaptive card", { conversationId, messageId });
+
+  return {
+    messageId,
+    conversationId,
+  };
+}
+
 /**
  * List all known conversation references (for debugging/CLI).
  */

extensions/nextcloud-talk/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/nextcloud-talk",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot Nextcloud Talk channel plugin",
   "clawdbot": {

extensions/nostr/CHANGELOG.md

@@ -1,6 +1,6 @@
 # Changelog
 
-## 2026.1.20-2
+## 2026.1.21
 
 ### Changes
 - Version alignment with core Clawdbot release numbers.

extensions/nostr/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/nostr",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot Nostr channel plugin for NIP-04 encrypted DMs",
   "clawdbot": {
@@ -25,7 +25,7 @@
   },
   "dependencies": {
     "clawdbot": "workspace:*",
-    "nostr-tools": "^2.10.4",
+    "nostr-tools": "^2.19.4",
     "zod": "^4.3.5"
   }
 }

extensions/signal/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/signal",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot Signal channel plugin",
   "clawdbot": {

extensions/slack/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/slack",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot Slack channel plugin",
   "clawdbot": {

extensions/telegram/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/telegram",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot Telegram channel plugin",
   "clawdbot": {

extensions/voice-call/CHANGELOG.md

@@ -1,6 +1,6 @@
 # Changelog
 
-## 2026.1.20-2
+## 2026.1.21
 
 ### Changes
 - Version alignment with core Clawdbot release numbers.

extensions/voice-call/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/voice-call",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot voice-call plugin",
   "dependencies": {

extensions/whatsapp/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/whatsapp",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot WhatsApp channel plugin",
   "clawdbot": {

extensions/zalo/CHANGELOG.md

@@ -1,6 +1,6 @@
 # Changelog
 
-## 2026.1.20-2
+## 2026.1.21
 
 ### Changes
 - Version alignment with core Clawdbot release numbers.

extensions/zalo/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/zalo",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot Zalo channel plugin",
   "clawdbot": {
@@ -28,6 +28,6 @@
   },
   "dependencies": {
     "clawdbot": "workspace:*",
-    "undici": "7.18.2"
+    "undici": "7.19.0"
   }
 }

extensions/zalouser/CHANGELOG.md

@@ -1,6 +1,6 @@
 # Changelog
 
-## 2026.1.20-2
+## 2026.1.21
 
 ### Changes
 - Version alignment with core Clawdbot release numbers.

extensions/zalouser/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@clawdbot/zalouser",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "type": "module",
   "description": "Clawdbot Zalo Personal Account plugin via zca-cli",
   "dependencies": {

package.json

@@ -1,6 +1,6 @@
 {
   "name": "clawdbot",
-  "version": "2026.1.20-2",
+  "version": "2026.1.21",
   "description": "WhatsApp gateway CLI (Baileys web) with Pi RPC agent",
   "type": "module",
   "main": "dist/index.js",
@@ -153,10 +153,10 @@
     "@grammyjs/transformer-throttler": "^1.2.1",
     "@homebridge/ciao": "^1.3.4",
     "@lydell/node-pty": "1.2.0-beta.3",
-    "@mariozechner/pi-agent-core": "0.49.2",
-    "@mariozechner/pi-ai": "0.49.2",
-    "@mariozechner/pi-coding-agent": "0.49.2",
-    "@mariozechner/pi-tui": "0.49.2",
+    "@mariozechner/pi-agent-core": "0.49.3",
+    "@mariozechner/pi-ai": "0.49.3",
+    "@mariozechner/pi-coding-agent": "0.49.3",
+    "@mariozechner/pi-tui": "0.49.3",
     "@mozilla/readability": "^0.6.0",
     "@sinclair/typebox": "0.34.47",
     "@slack/bolt": "^4.6.0",
@@ -166,7 +166,7 @@
     "body-parser": "^2.2.2",
     "chalk": "^5.6.2",
     "chokidar": "^5.0.0",
-    "chromium-bidi": "13.0.0",
+    "chromium-bidi": "13.0.1",
     "cli-highlight": "^2.1.11",
     "commander": "^14.0.2",
     "croner": "^9.1.0",
@@ -192,7 +192,7 @@
     "sqlite-vec": "0.1.7-alpha.2",
     "tar": "7.5.4",
     "tslog": "^4.10.2",
-    "undici": "^7.18.2",
+    "undici": "^7.19.0",
     "ws": "^8.19.0",
     "yaml": "^2.8.2",
     "zod": "^4.3.5"
@@ -209,7 +209,7 @@
     "@types/body-parser": "^1.19.6",
     "@types/express": "^5.0.6",
     "@types/markdown-it": "^14.1.2",
-    "@types/node": "^25.0.9",
+    "@types/node": "^25.0.10",
     "@types/proper-lockfile": "^4.1.4",
     "@types/qrcode-terminal": "^0.12.2",
     "@types/ws": "^8.18.1",

scripts/package-mac-app.sh

@@ -227,15 +227,29 @@ fi
 
 echo "📦 Copying Textual resources"
 TEXTUAL_BUNDLE_DIR="$(build_path_for_arch "$PRIMARY_ARCH")/$BUILD_CONFIG"
-TEXTUAL_BUNDLE="$TEXTUAL_BUNDLE_DIR/textual_Textual.bundle"
-if [ ! -d "$TEXTUAL_BUNDLE" ]; then
-  TEXTUAL_BUNDLE="$TEXTUAL_BUNDLE_DIR/Textual_Textual.bundle"
+TEXTUAL_BUNDLE=""
+for candidate in \
+  "$TEXTUAL_BUNDLE_DIR/textual_Textual.bundle" \
+  "$TEXTUAL_BUNDLE_DIR/Textual_Textual.bundle"
+do
+  if [ -d "$candidate" ]; then
+    TEXTUAL_BUNDLE="$candidate"
+    break
+  fi
+done
+if [ -z "$TEXTUAL_BUNDLE" ]; then
+  TEXTUAL_BUNDLE="$(find "$BUILD_ROOT" -type d \( -name "textual_Textual.bundle" -o -name "Textual_Textual.bundle" \) -print -quit)"
 fi
-if [ -d "$TEXTUAL_BUNDLE" ]; then
+if [ -n "$TEXTUAL_BUNDLE" ] && [ -d "$TEXTUAL_BUNDLE" ]; then
   rm -rf "$APP_ROOT/Contents/Resources/$(basename "$TEXTUAL_BUNDLE")"
   cp -R "$TEXTUAL_BUNDLE" "$APP_ROOT/Contents/Resources/"
 else
-  echo "WARN: Textual resource bundle not found in $TEXTUAL_BUNDLE_DIR (continuing)" >&2
+  if [[ "${ALLOW_MISSING_TEXTUAL_BUNDLE:-0}" == "1" ]]; then
+    echo "WARN: Textual resource bundle not found (continuing due to ALLOW_MISSING_TEXTUAL_BUNDLE=1)" >&2
+  else
+    echo "ERROR: Textual resource bundle not found. Set ALLOW_MISSING_TEXTUAL_BUNDLE=1 to bypass." >&2
+    exit 1
+  fi
 fi
 
 echo "⏹  Stopping any running Clawdbot"

skills/gog/SKILL.md

@@ -16,6 +16,7 @@ Setup (once)
 
 Common commands
 - Gmail search: `gog gmail search 'newer_than:7d' --max 10`
+- Gmail messages search (per email, ignores threading): `gog gmail messages search "in:inbox from:ryanair.com" --max 20 --account you@example.com`
 - Gmail send (plain): `gog gmail send --to a@b.com --subject "Hi" --body "Hello"`
 - Gmail send (multi-line): `gog gmail send --to a@b.com --subject "Hi" --body-file ./message.txt`
 - Gmail send (stdin): `gog gmail send --to a@b.com --subject "Hi" --body-file -`
@@ -88,3 +89,4 @@ Notes
 - Sheets values can be passed via `--values-json` (recommended) or as inline rows.
 - Docs supports export/cat/copy. In-place edits require a Docs API client (not in gog).
 - Confirm before sending mail or creating events.
+- `gog gmail search` returns one row per thread; use `gog gmail messages search` when you need every individual email returned separately.

src/agents/bash-tools.exec.ts

@@ -54,6 +54,7 @@ import { callGatewayTool } from "./tools/gateway.js";
 import { listNodes, resolveNodeIdFromList } from "./tools/nodes-utils.js";
 import { getShellConfig, sanitizeBinaryOutput } from "./shell-utils.js";
 import { buildCursorPositionResponse, stripDsrRequests } from "./pty-dsr.js";
+import { parseAgentSessionKey, resolveAgentIdFromSessionKey } from "../routing/session-key.js";
 
 const DEFAULT_MAX_OUTPUT = clampNumber(
   readEnvInt("PI_BASH_MAX_OUTPUT_CHARS"),
@@ -659,6 +660,11 @@ export function createExecTool(
   const notifyOnExit = defaults?.notifyOnExit !== false;
   const notifySessionKey = defaults?.sessionKey?.trim() || undefined;
   const approvalRunningNoticeMs = resolveApprovalRunningNoticeMs(defaults?.approvalRunningNoticeMs);
+  // Derive agentId only when sessionKey is an agent session key.
+  const parsedAgentSession = parseAgentSessionKey(defaults?.sessionKey);
+  const agentId =
+    defaults?.agentId ??
+    (parsedAgentSession ? resolveAgentIdFromSessionKey(defaults?.sessionKey) : undefined);
 
   return {
     name: "exec",
@@ -799,7 +805,7 @@ export function createExecTool(
 
       if (host === "node") {
         const approvals = resolveExecApprovals(
-          defaults?.agentId,
+          agentId,
           host === "node" ? { security: "allowlist" } : undefined,
         );
         const hostSecurity = minSecurity(security, approvals.agent.security);
@@ -865,7 +871,7 @@ export function createExecTool(
               cwd: workdir,
               env: nodeEnv,
               timeoutMs: typeof params.timeout === "number" ? params.timeout * 1000 : undefined,
-              agentId: defaults?.agentId,
+              agentId,
               sessionKey: defaults?.sessionKey,
               approved: approvedByAsk,
               approvalDecision: approvalDecision ?? undefined,
@@ -895,7 +901,7 @@ export function createExecTool(
                   host: "node",
                   security: hostSecurity,
                   ask: hostAsk,
-                  agentId: defaults?.agentId,
+                  agentId,
                   resolvedPath: null,
                   sessionKey: defaults?.sessionKey ?? null,
                   timeoutMs: DEFAULT_APPROVAL_TIMEOUT_MS,
@@ -1026,7 +1032,7 @@ export function createExecTool(
       }
 
       if (host === "gateway") {
-        const approvals = resolveExecApprovals(defaults?.agentId, { security: "allowlist" });
+        const approvals = resolveExecApprovals(agentId, { security: "allowlist" });
         const hostSecurity = minSecurity(security, approvals.agent.security);
         const hostAsk = maxAsk(ask, approvals.agent.ask);
         const askFallback = approvals.agent.askFallback;
@@ -1080,7 +1086,7 @@ export function createExecTool(
                   host: "gateway",
                   security: hostSecurity,
                   ask: hostAsk,
-                  agentId: defaults?.agentId,
+                  agentId,
                   resolvedPath,
                   sessionKey: defaults?.sessionKey ?? null,
                   timeoutMs: DEFAULT_APPROVAL_TIMEOUT_MS,
@@ -1123,7 +1129,7 @@ export function createExecTool(
                 for (const segment of analysis.segments) {
                   const pattern = segment.resolution?.resolvedPath ?? "";
                   if (pattern) {
-                    addAllowlistEntry(approvals.file, defaults?.agentId, pattern);
+                    addAllowlistEntry(approvals.file, agentId, pattern);
                   }
                 }
               }
@@ -1152,7 +1158,7 @@ export function createExecTool(
                 seen.add(match.pattern);
                 recordAllowlistUse(
                   approvals.file,
-                  defaults?.agentId,
+                  agentId,
                   match,
                   commandText,
                   resolvedPath ?? undefined,
@@ -1242,7 +1248,7 @@ export function createExecTool(
             seen.add(match.pattern);
             recordAllowlistUse(
               approvals.file,
-              defaults?.agentId,
+              agentId,
               match,
               params.command,
               analysis.segments[0]?.resolution?.resolvedPath,

src/agents/channel-tools.ts

@@ -1,4 +1,6 @@
+import { getChannelDock } from "../channels/dock.js";
 import { getChannelPlugin, listChannelPlugins } from "../channels/plugins/index.js";
+import { normalizeAnyChannelId } from "../channels/registry.js";
 import type { ChannelAgentTool, ChannelMessageActionName } from "../channels/plugins/types.js";
 import type { ClawdbotConfig } from "../config/config.js";
 
@@ -46,3 +48,19 @@ export function listChannelAgentTools(params: { cfg?: ClawdbotConfig }): Channel
   }
   return tools;
 }
+
+export function resolveChannelMessageToolHints(params: {
+  cfg?: ClawdbotConfig;
+  channel?: string | null;
+  accountId?: string | null;
+}): string[] {
+  const channelId = normalizeAnyChannelId(params.channel);
+  if (!channelId) return [];
+  const dock = getChannelDock(channelId);
+  const resolve = dock?.agentPrompt?.messageToolHints;
+  if (!resolve) return [];
+  const cfg = params.cfg ?? ({} as ClawdbotConfig);
+  return (resolve({ cfg, accountId: params.accountId }) ?? [])
+    .map((entry) => entry.trim())
+    .filter(Boolean);
+}

src/agents/pi-embedded-runner/compact.ts

@@ -5,7 +5,7 @@ import { createAgentSession, SessionManager, SettingsManager } from "@mariozechn
 
 import { resolveHeartbeatPrompt } from "../../auto-reply/heartbeat.js";
 import type { ReasoningLevel, ThinkLevel } from "../../auto-reply/thinking.js";
-import { listChannelSupportedActions } from "../channel-tools.js";
+import { listChannelSupportedActions, resolveChannelMessageToolHints } from "../channel-tools.js";
 import { resolveChannelCapabilities } from "../../config/channel-capabilities.js";
 import type { ClawdbotConfig } from "../../config/config.js";
 import { getMachineDisplayName } from "../../infra/machine-name.js";
@@ -245,6 +245,13 @@ export async function compactEmbeddedPiSession(params: {
               channel: runtimeChannel,
             })
           : undefined;
+        const messageToolHints = runtimeChannel
+          ? resolveChannelMessageToolHints({
+              cfg: params.config,
+              channel: runtimeChannel,
+              accountId: params.agentAccountId,
+            })
+          : undefined;
 
         const runtimeInfo = {
           host: machineName,
@@ -287,6 +294,7 @@ export async function compactEmbeddedPiSession(params: {
           docsPath: docsPath ?? undefined,
           promptMode,
           runtimeInfo,
+          messageToolHints,
           sandboxInfo,
           tools,
           modelAliasLines: buildModelAliasLines(params.config),

src/agents/pi-embedded-runner/run/attempt.ts

@@ -7,7 +7,10 @@ import { streamSimple } from "@mariozechner/pi-ai";
 import { createAgentSession, SessionManager, SettingsManager } from "@mariozechner/pi-coding-agent";
 
 import { resolveHeartbeatPrompt } from "../../../auto-reply/heartbeat.js";
-import { listChannelSupportedActions } from "../../channel-tools.js";
+import {
+  listChannelSupportedActions,
+  resolveChannelMessageToolHints,
+} from "../../channel-tools.js";
 import { resolveChannelCapabilities } from "../../../config/channel-capabilities.js";
 import { getMachineDisplayName } from "../../../infra/machine-name.js";
 import { resolveTelegramInlineButtonsScope } from "../../../telegram/inline-buttons.js";
@@ -260,6 +263,13 @@ export async function runEmbeddedAttempt(
           channel: runtimeChannel,
         })
       : undefined;
+    const messageToolHints = runtimeChannel
+      ? resolveChannelMessageToolHints({
+          cfg: params.config,
+          channel: runtimeChannel,
+          accountId: params.agentAccountId,
+        })
+      : undefined;
 
     const defaultModelRef = resolveDefaultModelForAgent({
       cfg: params.config ?? {},
@@ -305,6 +315,7 @@ export async function runEmbeddedAttempt(
       reactionGuidance,
       promptMode,
       runtimeInfo,
+      messageToolHints,
       sandboxInfo,
       tools,
       modelAliasLines: buildModelAliasLines(params.config),

src/agents/pi-embedded-runner/system-prompt.ts

@@ -35,6 +35,7 @@ export function buildEmbeddedSystemPrompt(params: {
     /** Supported message actions for the current channel (e.g., react, edit, unsend) */
     channelActions?: string[];
   };
+  messageToolHints?: string[];
   sandboxInfo?: EmbeddedSandboxInfo;
   tools: AgentTool[];
   modelAliasLines: string[];
@@ -56,6 +57,7 @@ export function buildEmbeddedSystemPrompt(params: {
     reactionGuidance: params.reactionGuidance,
     promptMode: params.promptMode,
     runtimeInfo: params.runtimeInfo,
+    messageToolHints: params.messageToolHints,
     sandboxInfo: params.sandboxInfo,
     toolNames: params.tools.map((tool) => tool.name),
     toolSummaries: buildToolSummaryMap(params.tools),

src/agents/system-prompt.ts

@@ -85,6 +85,7 @@ function buildMessagingSection(params: {
   messageChannelOptions: string;
   inlineButtonsEnabled: boolean;
   runtimeChannel?: string;
+  messageToolHints?: string[];
 }) {
   if (params.isMinimal) return [];
   return [
@@ -105,6 +106,7 @@ function buildMessagingSection(params: {
             : params.runtimeChannel
               ? `- Inline buttons not enabled for ${params.runtimeChannel}. If you need them, ask to set ${params.runtimeChannel}.capabilities.inlineButtons ("dm"|"group"|"all"|"allowlist").`
               : "",
+          ...(params.messageToolHints ?? []),
         ]
           .filter(Boolean)
           .join("\n")
@@ -159,6 +161,7 @@ export function buildAgentSystemPrompt(params: {
     channel?: string;
     capabilities?: string[];
   };
+  messageToolHints?: string[];
   sandboxInfo?: {
     enabled: boolean;
     workspaceDir?: string;
@@ -468,6 +471,7 @@ export function buildAgentSystemPrompt(params: {
       messageChannelOptions,
       inlineButtonsEnabled,
       runtimeChannel,
+      messageToolHints: params.messageToolHints,
     }),
   ];
 

src/agents/tools/cron-tool.test.ts

@@ -85,7 +85,7 @@ describe("cron tool", () => {
     });
   });
 
-  it("adds recent context for systemEvent reminders when session key is available", async () => {
+  it("adds recent context for systemEvent reminders when contextMessages > 0", async () => {
     callGatewayMock
       .mockResolvedValueOnce({
         messages: [
@@ -102,6 +102,7 @@ describe("cron tool", () => {
     const tool = createCronTool({ agentSessionKey: "main" });
     await tool.execute("call3", {
       action: "add",
+      contextMessages: 3,
       job: {
         name: "reminder",
         schedule: { atMs: 123 },
@@ -127,4 +128,64 @@ describe("cron tool", () => {
     expect(text).toContain("Assistant: We agreed to review on Tuesday.");
     expect(text).toContain("User: Remind me about the thing at 2pm");
   });
+
+  it("caps contextMessages at 10", async () => {
+    const messages = Array.from({ length: 12 }, (_, idx) => ({
+      role: "user",
+      content: [{ type: "text", text: `Message ${idx + 1}` }],
+    }));
+    callGatewayMock.mockResolvedValueOnce({ messages }).mockResolvedValueOnce({ ok: true });
+
+    const tool = createCronTool({ agentSessionKey: "main" });
+    await tool.execute("call5", {
+      action: "add",
+      contextMessages: 20,
+      job: {
+        name: "reminder",
+        schedule: { atMs: 123 },
+        payload: { kind: "systemEvent", text: "Reminder: the thing." },
+      },
+    });
+
+    expect(callGatewayMock).toHaveBeenCalledTimes(2);
+    const historyCall = callGatewayMock.mock.calls[0]?.[0] as {
+      method?: string;
+      params?: { limit?: number };
+    };
+    expect(historyCall.method).toBe("chat.history");
+    expect(historyCall.params?.limit).toBe(10);
+
+    const cronCall = callGatewayMock.mock.calls[1]?.[0] as {
+      params?: { payload?: { text?: string } };
+    };
+    const text = cronCall.params?.payload?.text ?? "";
+    expect(text).not.toMatch(/Message 1\\b/);
+    expect(text).not.toMatch(/Message 2\\b/);
+    expect(text).toContain("Message 3");
+    expect(text).toContain("Message 12");
+  });
+
+  it("does not add context when contextMessages is 0 (default)", async () => {
+    callGatewayMock.mockResolvedValueOnce({ ok: true });
+
+    const tool = createCronTool({ agentSessionKey: "main" });
+    await tool.execute("call4", {
+      action: "add",
+      job: {
+        name: "reminder",
+        schedule: { atMs: 123 },
+        payload: { text: "Reminder: the thing." },
+      },
+    });
+
+    // Should only call cron.add, not chat.history
+    expect(callGatewayMock).toHaveBeenCalledTimes(1);
+    const cronCall = callGatewayMock.mock.calls[0]?.[0] as {
+      method?: string;
+      params?: { payload?: { text?: string } };
+    };
+    expect(cronCall.method).toBe("cron.add");
+    const text = cronCall.params?.payload?.text ?? "";
+    expect(text).not.toContain("Recent context:");
+  });
 });

src/agents/tools/cron-tool.ts

@@ -16,7 +16,7 @@ const CRON_ACTIONS = ["status", "list", "add", "update", "remove", "run", "runs"
 
 const CRON_WAKE_MODES = ["now", "next-heartbeat"] as const;
 
-const REMINDER_CONTEXT_MESSAGES = 3;
+const REMINDER_CONTEXT_MESSAGES_MAX = 10;
 const REMINDER_CONTEXT_PER_MESSAGE_MAX = 220;
 const REMINDER_CONTEXT_TOTAL_MAX = 700;
 const REMINDER_CONTEXT_MARKER = "\n\nRecent context:\n";
@@ -34,6 +34,9 @@ const CronToolSchema = Type.Object({
   patch: Type.Optional(Type.Object({}, { additionalProperties: true })),
   text: Type.Optional(Type.String()),
   mode: optionalStringEnum(CRON_WAKE_MODES),
+  contextMessages: Type.Optional(
+    Type.Number({ minimum: 0, maximum: REMINDER_CONTEXT_MESSAGES_MAX }),
+  ),
 });
 
 type CronToolOptions = {
@@ -86,7 +89,13 @@ function extractMessageText(message: ChatMessage): { role: string; text: string
 async function buildReminderContextLines(params: {
   agentSessionKey?: string;
   gatewayOpts: GatewayCallOptions;
+  contextMessages: number;
 }) {
+  const maxMessages = Math.min(
+    REMINDER_CONTEXT_MESSAGES_MAX,
+    Math.max(0, Math.floor(params.contextMessages)),
+  );
+  if (maxMessages <= 0) return [];
   const sessionKey = params.agentSessionKey?.trim();
   if (!sessionKey) return [];
   const cfg = loadConfig();
@@ -95,13 +104,13 @@ async function buildReminderContextLines(params: {
   try {
     const res = (await callGatewayTool("chat.history", params.gatewayOpts, {
       sessionKey: resolvedKey,
-      limit: 12,
+      limit: maxMessages,
     })) as { messages?: unknown[] };
     const messages = Array.isArray(res?.messages) ? res.messages : [];
     const parsed = messages
       .map((msg) => extractMessageText(msg as ChatMessage))
       .filter((msg): msg is { role: string; text: string } => Boolean(msg));
-    const recent = parsed.slice(-REMINDER_CONTEXT_MESSAGES);
+    const recent = parsed.slice(-maxMessages);
     if (recent.length === 0) return [];
     const lines: string[] = [];
     let total = 0;
@@ -124,7 +133,7 @@ export function createCronTool(opts?: CronToolOptions): AnyAgentTool {
     label: "Cron",
     name: "cron",
     description:
-      "Manage Gateway cron jobs (status/list/add/update/remove/run/runs) and send wake events. Use `jobId` as the canonical identifier; `id` is accepted for compatibility.",
+      "Manage Gateway cron jobs (status/list/add/update/remove/run/runs) and send wake events. Use `jobId` as the canonical identifier; `id` is accepted for compatibility. Use `contextMessages` (0-10) to add previous messages as context to the job text.",
     parameters: CronToolSchema,
     execute: async (_toolCallId, args) => {
       const params = args as Record<string, unknown>;
@@ -149,6 +158,10 @@ export function createCronTool(opts?: CronToolOptions): AnyAgentTool {
             throw new Error("job required");
           }
           const job = normalizeCronJobCreate(params.job) ?? params.job;
+          const contextMessages =
+            typeof params.contextMessages === "number" && Number.isFinite(params.contextMessages)
+              ? params.contextMessages
+              : 0;
           if (
             job &&
             typeof job === "object" &&
@@ -160,6 +173,7 @@ export function createCronTool(opts?: CronToolOptions): AnyAgentTool {
               const contextLines = await buildReminderContextLines({
                 agentSessionKey: opts?.agentSessionKey,
                 gatewayOpts,
+                contextMessages,
               });
               if (contextLines.length > 0) {
                 const baseText = stripExistingContext(payload.text);

src/agents/tools/message-tool.ts

@@ -2,6 +2,7 @@ import { Type } from "@sinclair/typebox";
 import {
   listChannelMessageActions,
   supportsChannelMessageButtons,
+  supportsChannelMessageCards,
 } from "../../channels/plugins/message-actions.js";
 import {
   CHANNEL_MESSAGE_ACTION_NAMES,
@@ -36,7 +37,7 @@ function buildRoutingSchema() {
   };
 }
 
-function buildSendSchema(options: { includeButtons: boolean }) {
+function buildSendSchema(options: { includeButtons: boolean; includeCards: boolean }) {
   const props: Record<string, unknown> = {
     message: Type.Optional(Type.String()),
     effectId: Type.Optional(
@@ -77,8 +78,18 @@ function buildSendSchema(options: { includeButtons: boolean }) {
         },
       ),
     ),
+    card: Type.Optional(
+      Type.Object(
+        {},
+        {
+          additionalProperties: true,
+          description: "Adaptive Card JSON object (when supported by the channel)",
+        },
+      ),
+    ),
   };
   if (!options.includeButtons) delete props.buttons;
+  if (!options.includeCards) delete props.card;
   return props;
 }
 
@@ -192,7 +203,7 @@ function buildChannelManagementSchema() {
   };
 }
 
-function buildMessageToolSchemaProps(options: { includeButtons: boolean }) {
+function buildMessageToolSchemaProps(options: { includeButtons: boolean; includeCards: boolean }) {
   return {
     ...buildRoutingSchema(),
     ...buildSendSchema(options),
@@ -211,7 +222,7 @@ function buildMessageToolSchemaProps(options: { includeButtons: boolean }) {
 
 function buildMessageToolSchemaFromActions(
   actions: readonly string[],
-  options: { includeButtons: boolean },
+  options: { includeButtons: boolean; includeCards: boolean },
 ) {
   const props = buildMessageToolSchemaProps(options);
   return Type.Object({
@@ -222,6 +233,7 @@ function buildMessageToolSchemaFromActions(
 
 const MessageToolSchema = buildMessageToolSchemaFromActions(AllMessageActions, {
   includeButtons: true,
+  includeCards: true,
 });
 
 type MessageToolOptions = {
@@ -238,8 +250,10 @@ type MessageToolOptions = {
 function buildMessageToolSchema(cfg: ClawdbotConfig) {
   const actions = listChannelMessageActions(cfg);
   const includeButtons = supportsChannelMessageButtons(cfg);
+  const includeCards = supportsChannelMessageCards(cfg);
   return buildMessageToolSchemaFromActions(actions.length > 0 ? actions : ["send"], {
     includeButtons,
+    includeCards,
   });
 }
 

src/auto-reply/reply/agent-runner-utils.ts

@@ -1,7 +1,7 @@
 import type { NormalizedUsage } from "../../agents/usage.js";
 import { getChannelDock } from "../../channels/dock.js";
 import type { ChannelId, ChannelThreadingToolContext } from "../../channels/plugins/types.js";
-import { normalizeChannelId } from "../../channels/registry.js";
+import { normalizeAnyChannelId, normalizeChannelId } from "../../channels/registry.js";
 import type { ClawdbotConfig } from "../../config/config.js";
 import { isReasoningTagProvider } from "../../utils/provider-utils.js";
 import { estimateUsageCost, formatTokenCount, formatUsd } from "../../utils/usage-format.js";
@@ -23,7 +23,7 @@ export function buildThreadingToolContext(params: {
   if (!config) return {};
   const rawProvider = sessionCtx.Provider?.trim().toLowerCase();
   if (!rawProvider) return {};
-  const provider = normalizeChannelId(rawProvider);
+  const provider = normalizeChannelId(rawProvider) ?? normalizeAnyChannelId(rawProvider);
   // Fallback for unrecognized/plugin channels (e.g., BlueBubbles before plugin registry init)
   const dock = provider ? getChannelDock(provider) : undefined;
   if (!dock?.threading?.buildToolContext) {

src/channels/dock.ts

@@ -22,6 +22,7 @@ import type {
   ChannelElevatedAdapter,
   ChannelGroupAdapter,
   ChannelId,
+  ChannelAgentPromptAdapter,
   ChannelMentionAdapter,
   ChannelPlugin,
   ChannelThreadingAdapter,
@@ -51,6 +52,7 @@ export type ChannelDock = {
   groups?: ChannelGroupAdapter;
   mentions?: ChannelMentionAdapter;
   threading?: ChannelThreadingAdapter;
+  agentPrompt?: ChannelAgentPromptAdapter;
 };
 
 type ChannelDockStreaming = {
@@ -319,6 +321,7 @@ function buildDockFromPlugin(plugin: ChannelPlugin): ChannelDock {
     groups: plugin.groups,
     mentions: plugin.mentions,
     threading: plugin.threading,
+    agentPrompt: plugin.agentPrompt,
   };
 }
 

src/channels/plugins/message-actions.ts

@@ -21,6 +21,13 @@ export function supportsChannelMessageButtons(cfg: ClawdbotConfig): boolean {
   return false;
 }
 
+export function supportsChannelMessageCards(cfg: ClawdbotConfig): boolean {
+  for (const plugin of listChannelPlugins()) {
+    if (plugin.actions?.supportsCards?.({ cfg })) return true;
+  }
+  return false;
+}
+
 export async function dispatchChannelMessageAction(
   ctx: ChannelMessageActionContext,
 ): Promise<AgentToolResult<unknown> | null> {

src/channels/plugins/types.core.ts

@@ -240,6 +240,10 @@ export type ChannelMessagingAdapter = {
   }) => string;
 };
 
+export type ChannelAgentPromptAdapter = {
+  messageToolHints?: (params: { cfg: ClawdbotConfig; accountId?: string | null }) => string[];
+};
+
 export type ChannelDirectoryEntryKind = "user" | "group" | "channel";
 
 export type ChannelDirectoryEntry = {
@@ -281,6 +285,7 @@ export type ChannelMessageActionAdapter = {
   listActions?: (params: { cfg: ClawdbotConfig }) => ChannelMessageActionName[];
   supportsAction?: (params: { action: ChannelMessageActionName }) => boolean;
   supportsButtons?: (params: { cfg: ClawdbotConfig }) => boolean;
+  supportsCards?: (params: { cfg: ClawdbotConfig }) => boolean;
   extractToolSend?: (params: { args: Record<string, unknown> }) => ChannelToolSend | null;
   handleAction?: (ctx: ChannelMessageActionContext) => Promise<AgentToolResult<unknown>>;
 };

src/channels/plugins/types.plugin.ts

@@ -20,6 +20,7 @@ import type {
   ChannelAgentToolFactory,
   ChannelCapabilities,
   ChannelId,
+  ChannelAgentPromptAdapter,
   ChannelMentionAdapter,
   ChannelMessageActionAdapter,
   ChannelMessagingAdapter,
@@ -73,6 +74,7 @@ export type ChannelPlugin<ResolvedAccount = any> = {
   streaming?: ChannelStreamingAdapter;
   threading?: ChannelThreadingAdapter;
   messaging?: ChannelMessagingAdapter;
+  agentPrompt?: ChannelAgentPromptAdapter;
   directory?: ChannelDirectoryAdapter;
   resolver?: ChannelResolverAdapter;
   actions?: ChannelMessageActionAdapter;

src/channels/plugins/types.ts

@@ -31,6 +31,7 @@ export type {
 export type {
   ChannelAccountSnapshot,
   ChannelAccountState,
+  ChannelAgentPromptAdapter,
   ChannelAgentTool,
   ChannelAgentToolFactory,
   ChannelCapabilities,

src/cli/memory-cli.ts

@@ -323,9 +323,11 @@ export async function runMemoryStatus(opts: MemoryCommandOptions) {
     }
     if (status.vector) {
       const vectorState = status.vector.enabled
-        ? status.vector.available
-          ? "ready"
-          : "unavailable"
+        ? status.vector.available === undefined
+          ? "unknown"
+          : status.vector.available
+            ? "ready"
+            : "unavailable"
         : "disabled";
       const vectorColor =
         vectorState === "ready"

src/cli/nodes-cli/register.invoke.ts

@@ -267,8 +267,8 @@ export function registerNodesInvokeCommands(nodes: Command) {
               security: hostSecurity,
               ask: hostAsk,
               agentId,
-              resolvedPath: null,
-              sessionKey: null,
+              resolvedPath: undefined,
+              sessionKey: undefined,
               timeoutMs: 120_000,
             })) as { decision?: string } | null;
             const decision =

src/cli/program/message/helpers.ts

@@ -5,6 +5,7 @@ import { CHANNEL_TARGET_DESCRIPTION } from "../../../infra/outbound/channel-targ
 import { defaultRuntime } from "../../../runtime.js";
 import { createDefaultDeps } from "../../deps.js";
 import { runCommandWithRuntime } from "../../cli-utils.js";
+import { ensurePluginRegistryLoaded } from "../../plugin-registry.js";
 
 export type MessageCliHelpers = {
   withMessageBase: (command: Command) => Command;
@@ -32,6 +33,7 @@ export function createMessageCliHelpers(
 
   const runMessageAction = async (action: string, opts: Record<string, unknown>) => {
     setVerbose(Boolean(opts.verbose));
+    ensurePluginRegistryLoaded();
     const deps = createDefaultDeps();
     await runCommandWithRuntime(
       defaultRuntime,

src/cli/program/message/register.send.ts

@@ -19,6 +19,7 @@ export function registerMessageSendCommand(message: Command, helpers: MessageCli
           "--buttons <json>",
           "Telegram inline keyboard buttons as JSON (array of button rows)",
         )
+        .option("--card <json>", "Adaptive Card JSON object (when supported by the channel)")
         .option("--reply-to <id>", "Reply-to message id")
         .option("--thread-id <id>", "Thread id (Telegram forum thread)")
         .option("--gif-playback", "Treat video media as GIF playback (WhatsApp only).", false),

src/cli/update-cli.test.ts

@@ -236,7 +236,7 @@ describe("update-cli", () => {
         durationMs: 100,
       });
 
-      await updateCommand({});
+      await updateCommand({ yes: true });
 
       const call = vi.mocked(runGatewayUpdate).mock.calls[0]?.[0];
       expect(call?.channel).toBe("stable");
@@ -273,7 +273,7 @@ describe("update-cli", () => {
     try {
       await fs.writeFile(
         path.join(tempDir, "package.json"),
-        JSON.stringify({ name: "clawdbot", version: "2026.1.18-1" }),
+        JSON.stringify({ name: "clawdbot", version: "1.0.0" }),
         "utf-8",
       );
 
@@ -302,7 +302,7 @@ describe("update-cli", () => {
       });
       vi.mocked(resolveNpmChannelTag).mockResolvedValue({
         tag: "latest",
-        version: "2026.1.20-1",
+        version: "1.2.3-1",
       });
       vi.mocked(runGatewayUpdate).mockResolvedValue({
         status: "ok",

src/cli/update-cli.ts

@@ -589,16 +589,20 @@ export async function updateCommand(opts: UpdateCommandOptions): Promise<void> {
   let tag = explicitTag ?? channelToNpmTag(channel);
   if (updateInstallKind !== "git") {
     const currentVersion = switchToPackage ? null : await readPackageVersion(root);
+    let fallbackToLatest = false;
     const targetVersion = explicitTag
       ? await resolveTargetVersion(tag, timeoutMs)
       : await resolveNpmChannelTag({ channel, timeoutMs }).then((resolved) => {
           tag = resolved.tag;
+          fallbackToLatest = channel === "beta" && resolved.tag === "latest";
           return resolved.version;
         });
     const cmp =
       currentVersion && targetVersion ? compareSemverStrings(currentVersion, targetVersion) : null;
     const needsConfirm =
-      currentVersion != null && (targetVersion == null || (cmp != null && cmp > 0));
+      !fallbackToLatest &&
+      currentVersion != null &&
+      (targetVersion == null || (cmp != null && cmp > 0));
 
     if (needsConfirm && !opts.yes) {
       if (!process.stdin.isTTY || opts.json) {

src/config/io.ts

@@ -247,7 +247,7 @@ export function createConfigIO(overrides: ConfigIoDeps = {}) {
           .join("\n");
         if (!loggedInvalidConfigs.has(configPath)) {
           loggedInvalidConfigs.add(configPath);
-          deps.logger.error(`Invalid config:\\n${details}`);
+          deps.logger.error(`Invalid config at ${configPath}:\\n${details}`);
         }
         const error = new Error("Invalid config");
         (error as { code?: string; details?: string }).code = "INVALID_CONFIG";
@@ -299,6 +299,10 @@ export function createConfigIO(overrides: ConfigIoDeps = {}) {
         deps.logger.error(err.message);
         throw err;
       }
+      const error = err as { code?: string };
+      if (error?.code === "INVALID_CONFIG") {
+        return {};
+      }
       deps.logger.error(`Failed to read config at ${configPath}`, err);
       return {};
     }

src/config/types.msteams.ts

@@ -78,4 +78,8 @@ export type MSTeamsConfig = {
   replyStyle?: MSTeamsReplyStyle;
   /** Per-team config. Key is team ID (from the /team/ URL path segment). */
   teams?: Record<string, MSTeamsTeamConfig>;
+  /** Max media size in MB (default: 100MB for OneDrive upload support). */
+  mediaMaxMb?: number;
+  /** SharePoint site ID for file uploads in group chats/channels (e.g., "contoso.sharepoint.com,guid1,guid2"). */
+  sharePointSiteId?: string;
 };

src/config/zod-schema.providers-core.ts

@@ -599,6 +599,10 @@ export const MSTeamsConfigSchema = z
     dms: z.record(z.string(), DmConfigSchema.optional()).optional(),
     replyStyle: MSTeamsReplyStyleSchema.optional(),
     teams: z.record(z.string(), MSTeamsTeamSchema.optional()).optional(),
+    /** Max media size in MB (default: 100MB for OneDrive upload support). */
+    mediaMaxMb: z.number().positive().optional(),
+    /** SharePoint site ID for file uploads in group chats/channels (e.g., "contoso.sharepoint.com,guid1,guid2") */
+    sharePointSiteId: z.string().optional(),
   })
   .strict()
   .superRefine((value, ctx) => {