fix: clarify test comment and use exact assertions

Address Gemini review feedback:
- Fix misleading comment: \u{00e9} is precomposed e-acute, not combining accent
- Replace weak assertions (ends_with/is_empty) with exact assert_eq!

Co-Authored-By: Claude Opus 4.6 (1M context) <[email protected]>

src/channels/relay/client.rs

@@ -122,18 +122,32 @@ impl RelayClient {
     /// instance_url in chat-api. IronClaw only passes an optional CSRF nonce
     /// for validating the callback — no URLs.
     pub async fn initiate_oauth(&self, state_nonce: Option<&str>) -> Result<String, RelayError> {
+        let url = format!("{}/oauth/slack/auth", self.base_url);
+        tracing::debug!(relay_url = %url, "RelayClient::initiate_oauth: sending request");
         let mut query: Vec<(&str, &str)> = vec![];
         if let Some(nonce) = state_nonce {
             query.push(("state_nonce", nonce));
         }
         let resp = self
             .http
-            .get(format!("{}/oauth/slack/auth", self.base_url))
+            .get(&url)
             .bearer_auth(self.api_key.expose_secret())
             .query(&query)
             .send()
             .await
-            .map_err(|e| RelayError::Network(e.to_string()))?;
+            .map_err(|e| {
+                tracing::warn!(
+                    relay_url = %url,
+                    error = %e,
+                    "RelayClient::initiate_oauth: network request failed"
+                );
+                RelayError::Network(e.to_string())
+            })?;
+        tracing::debug!(
+            relay_url = %url,
+            status = %resp.status(),
+            "RelayClient::initiate_oauth: received response"
+        );
 
         let status = resp.status();
         if status.is_redirection() {
@@ -224,20 +238,39 @@ impl RelayClient {
         method: &str,
         body: serde_json::Value,
     ) -> Result<serde_json::Value, RelayError> {
+        let url = format!("{}/proxy/{}/{}", self.base_url, provider, method);
+        tracing::debug!(
+            relay_url = %url,
+            provider = %provider,
+            method = %method,
+            "RelayClient::proxy_provider: sending request"
+        );
         let query: Vec<(&str, &str)> = vec![("team_id", team_id)];
         let resp = self
             .http
-            .post(format!("{}/proxy/{}/{}", self.base_url, provider, method))
+            .post(&url)
             .bearer_auth(self.api_key.expose_secret())
             .query(&query)
             .json(&body)
             .send()
             .await
-            .map_err(|e| RelayError::Network(e.to_string()))?;
+            .map_err(|e| {
+                tracing::warn!(
+                    relay_url = %url,
+                    error = %e,
+                    "RelayClient::proxy_provider: network request failed"
+                );
+                RelayError::Network(e.to_string())
+            })?;
 
         if !resp.status().is_success() {
             let status = resp.status().as_u16();
             let body = resp.text().await.unwrap_or_default();
+            tracing::warn!(
+                relay_url = %url,
+                status = status,
+                "RelayClient::proxy_provider: channel-relay returned error"
+            );
             return Err(RelayError::Api {
                 status,
                 message: body,
@@ -255,23 +288,45 @@ impl RelayClient {
     /// 32-byte secret. Called once at activation time; the result is cached in the
     /// extension manager so subsequent calls to `relay_signing_secret()` use it.
     pub async fn get_signing_secret(&self, team_id: &str) -> Result<Vec<u8>, RelayError> {
+        let url = format!("{}/relay/signing-secret", self.base_url);
+        tracing::debug!(
+            relay_url = %url,
+            "RelayClient::get_signing_secret: fetching signing secret"
+        );
         let resp = self
             .http
-            .get(format!("{}/relay/signing-secret", self.base_url))
+            .get(&url)
             .bearer_auth(self.api_key.expose_secret())
             .query(&[("team_id", team_id)])
             .send()
             .await
-            .map_err(|e| RelayError::Network(e.to_string()))?;
+            .map_err(|e| {
+                tracing::warn!(
+                    relay_url = %url,
+                    error = %e,
+                    "RelayClient::get_signing_secret: network request failed"
+                );
+                RelayError::Network(e.to_string())
+            })?;
 
         if !resp.status().is_success() {
             let status = resp.status().as_u16();
             let body = resp.text().await.unwrap_or_default();
+            tracing::warn!(
+                relay_url = %url,
+                status = status,
+                body = %body,
+                "RelayClient::get_signing_secret: channel-relay returned error"
+            );
             return Err(RelayError::Api {
                 status,
                 message: body,
             });
         }
+        tracing::debug!(
+            relay_url = %url,
+            "RelayClient::get_signing_secret: received successful response"
+        );
 
         let body: serde_json::Value = resp
             .json()

src/channels/web/server.rs

@@ -1177,11 +1177,31 @@ async fn slack_relay_oauth_callback_handler(
 
         // Store team_id in settings
         let team_id_key = format!("relay:{}:team_id", DEFAULT_RELAY_NAME);
-        let _ = store
+        tracing::info!(
+            relay = DEFAULT_RELAY_NAME,
+            owner_id = %state.owner_id,
+            team_id_key = %team_id_key,
+            "relay OAuth callback: storing team_id in settings"
+        );
+        store
             .set_setting(&state.owner_id, &team_id_key, &serde_json::json!(team_id))
-            .await;
+            .await
+            .map_err(|e| {
+                tracing::error!(
+                    relay = DEFAULT_RELAY_NAME,
+                    owner_id = %state.owner_id,
+                    error = %e,
+                    "relay OAuth callback: failed to persist team_id to settings store"
+                );
+                format!("Failed to persist relay team_id: {e}")
+            })?;
 
         // Activate the relay channel
+        tracing::info!(
+            relay = DEFAULT_RELAY_NAME,
+            owner_id = %state.owner_id,
+            "relay OAuth callback: activating relay channel"
+        );
         ext_mgr
             .activate_stored_relay(DEFAULT_RELAY_NAME, &state.owner_id)
             .await
@@ -2181,6 +2201,11 @@ async fn extensions_activate_handler(
     AuthenticatedUser(user): AuthenticatedUser,
     Path(name): Path<String>,
 ) -> Result<Json<ActionResponse>, (StatusCode, String)> {
+    tracing::debug!(
+        extension = %name,
+        user_id = %user.user_id,
+        "extensions_activate_handler: received activate request"
+    );
     let ext_mgr = state.extension_manager.as_ref().ok_or((
         StatusCode::NOT_IMPLEMENTED,
         "Extension manager not available (secrets store required)".to_string(),
@@ -2188,6 +2213,10 @@ async fn extensions_activate_handler(
 
     match ext_mgr.activate(&name, &user.user_id).await {
         Ok(result) => {
+            tracing::info!(
+                extension = %name,
+                "extensions_activate_handler: activation succeeded"
+            );
             // Activation loaded the WASM module. Check if the tool needs
             // OAuth scope expansion (e.g., adding google-docs when gmail
             // already has a token but missing the documents scope).
@@ -2206,6 +2235,13 @@ async fn extensions_activate_handler(
                 crate::extensions::ExtensionError::AuthRequired
             );
 
+            tracing::debug!(
+                extension = %name,
+                error = %activate_err,
+                needs_auth = needs_auth,
+                "extensions_activate_handler: activation failed, attempting auth fallback"
+            );
+
             if !needs_auth {
                 return Ok(Json(ActionResponse::fail(activate_err.to_string())));
             }
@@ -2213,10 +2249,21 @@ async fn extensions_activate_handler(
             // Activation failed due to auth; try authenticating first.
             match ext_mgr.auth(&name, &user.user_id).await {
                 Ok(auth_result) if auth_result.is_authenticated() => {
+                    tracing::debug!(
+                        extension = %name,
+                        "extensions_activate_handler: auth reports authenticated, retrying activate"
+                    );
                     // Auth succeeded, retry activation.
                     match ext_mgr.activate(&name, &user.user_id).await {
                         Ok(result) => Ok(Json(ActionResponse::ok(result.message))),
-                        Err(e) => Ok(Json(ActionResponse::fail(e.to_string()))),
+                        Err(e) => {
+                            tracing::warn!(
+                                extension = %name,
+                                error = %e,
+                                "extensions_activate_handler: retry after auth still failed"
+                            );
+                            Ok(Json(ActionResponse::fail(e.to_string())))
+                        }
                     }
                 }
                 Ok(auth_result) => {

src/cli/config.rs

@@ -127,7 +127,8 @@ async fn list_settings(
         }
 
         let display_value = if value.len() > 60 {
-            format!("{}...", &value[..57])
+            let end = crate::util::floor_char_boundary(&value, 57);
+            format!("{}...", &value[..end])
         } else {
             value
         };

src/cli/memory.rs

@@ -256,7 +256,8 @@ fn truncate_content(s: &str, max_len: usize) -> String {
     if s.len() <= max_len {
         s.to_string()
     } else {
-        format!("{}...", &s[..max_len])
+        let end = crate::util::floor_char_boundary(s, max_len);
+        format!("{}...", &s[..end])
     }
 }
 
@@ -292,4 +293,17 @@ mod tests {
         assert_eq!(truncate_content("hello", 10), "hello");
         assert_eq!(truncate_content("hello world", 5), "hello...");
     }
+
+    #[test]
+    fn test_truncate_content_multibyte_does_not_panic() {
+        // \u{00e9} is precomposed 'é' (2 bytes in UTF-8)
+        let s = "caf\u{00e9} au lait"; // "café au lait", é starts at byte 3
+        let result = truncate_content(s, 4); // byte 4 is inside 2-byte é
+        assert_eq!(result, "caf...");
+
+        // 4-byte emoji: slicing mid-emoji must not panic
+        let emoji = "Hi \u{1F600} there"; // 😀 is 4 bytes, starts at byte 3
+        let result = truncate_content(emoji, 4); // byte 4 is inside 😀
+        assert_eq!(result, "Hi ...");
+    }
 }

src/context/state.rs

@@ -192,6 +192,9 @@ pub struct JobContext {
     /// but subsequent tools (e.g., `json`) may need the full output. This
     /// stash stores the complete, unsanitized output so tools can reference
     /// previous results by ID via `$tool_call_id` parameter syntax.
+    ///
+    /// Also used for cross-tool implicit state (keys prefixed with `__`) such
+    /// as `__routine_last_name` for fallback recovery in routine tool chains.
     #[serde(skip)]
     pub tool_output_stash: Arc<tokio::sync::RwLock<HashMap<String, String>>>,
     /// User's preferred timezone (IANA name, e.g. "America/New_York"). Defaults to "UTC".

src/extensions/manager.rs

@@ -659,6 +659,66 @@ impl ExtensionManager {
         })
     }
 
+    /// Resolve the relay URL override for an extension from settings.
+    ///
+    /// Returns `Some(url)` if a non-empty per-extension `relay_url` override is
+    /// set for the given extension; otherwise returns `None` and callers should
+    /// fall back to the env-level `RelayConfig`.
+    ///
+    /// Uses `self.user_id` (owner scope) for consistency with `configure()`,
+    /// which also writes setting_path fields under the owner scope.
+    ///
+    /// The override is validated: only `http` / `https` schemes are accepted
+    /// and the URL must not contain userinfo (embedded credentials).  This
+    /// prevents a malicious override from exfiltrating the instance-wide relay
+    /// API key to an attacker-controlled host.
+    async fn effective_relay_url(&self, name: &str) -> Option<String> {
+        if let Some(ref store) = self.store {
+            let key = format!("extensions.{name}.relay_url");
+            if let Ok(Some(v)) = store.get_setting(&self.user_id, &key).await {
+                let url = v
+                    .as_str()
+                    .map(|s| s.trim().to_string())
+                    .filter(|s| !s.is_empty());
+                if let Some(ref u) = url {
+                    // Validate the override to prevent API-key exfiltration:
+                    // only allow http(s) with no embedded credentials.
+                    match url::Url::parse(u) {
+                        Ok(parsed)
+                            if (parsed.scheme() == "http" || parsed.scheme() == "https")
+                                && parsed.username().is_empty()
+                                && parsed.password().is_none() =>
+                        {
+                            tracing::debug!(
+                                extension = %name,
+                                relay_url_host = %parsed.host_str().unwrap_or("unknown"),
+                                "effective_relay_url: using per-extension override from settings"
+                            );
+                            return url;
+                        }
+                        Ok(parsed) => {
+                            tracing::warn!(
+                                extension = %name,
+                                scheme = %parsed.scheme(),
+                                has_userinfo = !parsed.username().is_empty() || parsed.password().is_some(),
+                                "effective_relay_url: rejecting override — \
+                                 only http/https without embedded credentials is allowed"
+                            );
+                        }
+                        Err(e) => {
+                            tracing::warn!(
+                                extension = %name,
+                                error = %e,
+                                "effective_relay_url: rejecting override — invalid URL"
+                            );
+                        }
+                    }
+                }
+            }
+        }
+        None
+    }
+
     /// Get the shared relay event sender for the webhook endpoint.
     pub fn relay_event_tx(
         &self,
@@ -892,6 +952,46 @@ impl ExtensionManager {
         false
     }
 
+    /// Check whether a stored `team_id` setting exists for the given relay extension.
+    ///
+    /// Unlike [`is_relay_channel`], this does **not** consult the in-memory
+    /// `installed_relay_extensions` set — it only looks at the persistent settings
+    /// store.  This distinction matters for `auth_channel_relay`: an extension can
+    /// be *installed* (present in the in-memory set) but not yet *authenticated*
+    /// (no OAuth completed, no team_id stored).
+    async fn has_stored_team_id(&self, name: &str, _user_id: &str) -> bool {
+        if let Some(ref store) = self.store {
+            let key = format!("relay:{}:team_id", name);
+            // Use owner scope (self.user_id) for consistency: the OAuth callback
+            // stores team_id under state.owner_id which maps to self.user_id.
+            match store.get_setting(&self.user_id, &key).await {
+                Ok(Some(v)) => {
+                    let has_id = v.as_str().is_some_and(|s| !s.is_empty());
+                    tracing::debug!(
+                        extension = %name,
+                        has_team_id = has_id,
+                        "has_stored_team_id: checked store"
+                    );
+                    return has_id;
+                }
+                Ok(None) => {
+                    tracing::debug!(
+                        extension = %name,
+                        "has_stored_team_id: no team_id setting found"
+                    );
+                }
+                Err(e) => {
+                    tracing::warn!(
+                        extension = %name,
+                        error = %e,
+                        "has_stored_team_id: failed to read from settings store"
+                    );
+                }
+            }
+        }
+        false
+    }
+
     /// Restore persisted relay channels after startup.
     ///
     /// Loads the persisted active channel list, filters to relay types (those with
@@ -1418,7 +1518,7 @@ impl ExtensionManager {
             let errors = self.activation_errors.read().await;
             for name in installed.iter() {
                 let active = active_names.contains(name);
-                let authenticated = self.is_relay_channel(name, user_id).await;
+                let authenticated = self.has_stored_team_id(name, user_id).await;
                 let activation_error = errors.get(name).cloned();
                 let registry_entry = self
                     .registry
@@ -4191,20 +4291,69 @@ impl ExtensionManager {
         name: &str,
         user_id: &str,
     ) -> Result<AuthResult, ExtensionError> {
-        // Check if already authenticated (team_id setting exists)
-        if self.is_relay_channel(name, user_id).await {
+        tracing::debug!(
+            extension = %name,
+            user_id = %user_id,
+            "auth_channel_relay: starting"
+        );
+
+        // Check if already authenticated by looking for a stored team_id.
+        // We intentionally skip the `installed_relay_extensions` in-memory set
+        // here because that set only tracks *installed* extensions — an extension
+        // can be installed (via registry) but not yet authenticated (no OAuth
+        // completed). Checking just `is_relay_channel()` would short-circuit
+        // to "authenticated" even when no team_id exists, preventing the OAuth
+        // flow from being offered to the user.
+        if self.has_stored_team_id(name, user_id).await {
+            tracing::debug!(
+                extension = %name,
+                "auth_channel_relay: already authenticated (team_id in store)"
+            );
             return Ok(AuthResult::authenticated(name, ExtensionKind::ChannelRelay));
         }
 
+        tracing::debug!(
+            extension = %name,
+            "auth_channel_relay: no stored team_id, initiating OAuth"
+        );
+
         // Use relay config captured at startup
-        let relay_config = self.relay_config()?;
+        let relay_config = self.relay_config().map_err(|e| {
+            tracing::warn!(
+                extension = %name,
+                error = %e,
+                "auth_channel_relay: relay config not available — \
+                 CHANNEL_RELAY_URL and CHANNEL_RELAY_API_KEY must be set"
+            );
+            e
+        })?;
+
+        // Allow per-extension URL override from settings
+        let effective_url = self
+            .effective_relay_url(name)
+            .await
+            .unwrap_or_else(|| relay_config.url.clone());
+
+        tracing::debug!(
+            extension = %name,
+            relay_url = %effective_url,
+            "auth_channel_relay: creating relay client for OAuth"
+        );
 
         let client = crate::channels::relay::RelayClient::new(
-            relay_config.url.clone(),
+            effective_url.clone(),
             relay_config.api_key.clone(),
             relay_config.request_timeout_secs,
         )
-        .map_err(|e| ExtensionError::Config(e.to_string()))?;
+        .map_err(|e| {
+            tracing::warn!(
+                extension = %name,
+                relay_url = %effective_url,
+                error = %e,
+                "auth_channel_relay: failed to create relay HTTP client"
+            );
+            ExtensionError::Config(e.to_string())
+        })?;
 
         // Generate CSRF nonce — IronClaw validates this on the callback to ensure
         // the OAuth completion is legitimate. Channel-relay embeds it in the signed
@@ -4216,18 +4365,44 @@ impl ExtensionManager {
         self.secrets
             .create(user_id, CreateSecretParams::new(&state_key, &state_nonce))
             .await
-            .map_err(|e| ExtensionError::AuthFailed(format!("Failed to store OAuth state: {e}")))?;
+            .map_err(|e| {
+                tracing::warn!(
+                    extension = %name,
+                    error = %e,
+                    "auth_channel_relay: failed to store OAuth state nonce"
+                );
+                ExtensionError::AuthFailed(format!("Failed to store OAuth state: {e}"))
+            })?;
 
         // Channel-relay derives all URLs from trusted instance_url in chat-api.
         // We only pass the nonce for CSRF validation on the callback.
+        tracing::debug!(
+            extension = %name,
+            relay_url = %effective_url,
+            "auth_channel_relay: calling initiate_oauth on channel-relay"
+        );
         match client.initiate_oauth(Some(&state_nonce)).await {
-            Ok(auth_url) => Ok(AuthResult::awaiting_authorization(
-                name,
-                ExtensionKind::ChannelRelay,
-                auth_url,
-                "redirect".to_string(),
-            )),
-            Err(e) => Err(ExtensionError::AuthFailed(e.to_string())),
+            Ok(auth_url) => {
+                tracing::info!(
+                    extension = %name,
+                    "auth_channel_relay: OAuth URL obtained, awaiting user authorization"
+                );
+                Ok(AuthResult::awaiting_authorization(
+                    name,
+                    ExtensionKind::ChannelRelay,
+                    auth_url,
+                    "redirect".to_string(),
+                ))
+            }
+            Err(e) => {
+                tracing::warn!(
+                    extension = %name,
+                    relay_url = %effective_url,
+                    error = %e,
+                    "auth_channel_relay: initiate_oauth call to channel-relay failed"
+                );
+                Err(ExtensionError::AuthFailed(e.to_string()))
+            }
         }
     }
 
@@ -4237,40 +4412,112 @@ impl ExtensionManager {
         name: &str,
         user_id: &str,
     ) -> Result<ActivateResult, ExtensionError> {
+        tracing::debug!(
+            extension = %name,
+            user_id = %user_id,
+            "activate_channel_relay: starting"
+        );
+
         let team_id_key = format!("relay:{}:team_id", name);
 
         // Get team_id from settings (stored by the OAuth callback)
         let team_id = if let Some(ref store) = self.store {
-            store
-                .get_setting(user_id, &team_id_key)
-                .await
-                .ok()
-                .flatten()
-                .and_then(|v| v.as_str().map(|s| s.to_string()))
-                .unwrap_or_default()
+            match store.get_setting(user_id, &team_id_key).await {
+                Ok(Some(v)) => {
+                    let id = v.as_str().map(|s| s.to_string()).unwrap_or_default();
+                    tracing::debug!(
+                        extension = %name,
+                        team_id_empty = id.is_empty(),
+                        "activate_channel_relay: loaded team_id from store"
+                    );
+                    id
+                }
+                Ok(None) => {
+                    tracing::debug!(
+                        extension = %name,
+                        setting_key = %team_id_key,
+                        "activate_channel_relay: no team_id in settings store"
+                    );
+                    String::new()
+                }
+                Err(e) => {
+                    tracing::warn!(
+                        extension = %name,
+                        error = %e,
+                        "activate_channel_relay: failed to read team_id from settings store"
+                    );
+                    String::new()
+                }
+            }
         } else {
+            tracing::debug!(
+                extension = %name,
+                "activate_channel_relay: no settings store available"
+            );
             String::new()
         };
 
         if team_id.is_empty() {
+            tracing::debug!(
+                extension = %name,
+                "activate_channel_relay: team_id is empty, returning AuthRequired"
+            );
             return Err(ExtensionError::AuthRequired);
         }
 
         // Use relay config captured at startup
-        let relay_config = self.relay_config()?;
+        let relay_config = self.relay_config().map_err(|e| {
+            tracing::warn!(
+                extension = %name,
+                error = %e,
+                "activate_channel_relay: relay config not available"
+            );
+            e
+        })?;
+
+        // Allow per-extension URL override from settings
+        let effective_url = self
+            .effective_relay_url(name)
+            .await
+            .unwrap_or_else(|| relay_config.url.clone());
+
+        tracing::debug!(
+            extension = %name,
+            relay_url = %effective_url,
+            "activate_channel_relay: relay config loaded"
+        );
 
         let instance_id = self.relay_instance_id(relay_config, user_id);
 
         let client = crate::channels::relay::RelayClient::new(
-            relay_config.url.clone(),
+            effective_url.clone(),
             relay_config.api_key.clone(),
             relay_config.request_timeout_secs,
         )
-        .map_err(|e| ExtensionError::ActivationFailed(e.to_string()))?;
+        .map_err(|e| {
+            tracing::warn!(
+                extension = %name,
+                relay_url = %effective_url,
+                error = %e,
+                "activate_channel_relay: failed to create relay HTTP client"
+            );
+            ExtensionError::ActivationFailed(e.to_string())
+        })?;
 
         // Fetch the per-instance signing secret from channel-relay.
         // This must succeed — there is no fallback.
+        tracing::debug!(
+            extension = %name,
+            relay_url = %effective_url,
+            "activate_channel_relay: fetching signing secret from channel-relay"
+        );
         let signing_secret = client.get_signing_secret(&team_id).await.map_err(|e| {
+            tracing::warn!(
+                extension = %name,
+                relay_url = %effective_url,
+                error = %e,
+                "activate_channel_relay: failed to fetch signing secret from channel-relay"
+            );
             ExtensionError::Config(format!("Failed to fetch relay signing secret: {e}"))
         })?;
 
@@ -4289,16 +4536,29 @@ impl ExtensionManager {
         // Hot-add to channel manager
         let cm_guard = self.relay_channel_manager.read().await;
         let channel_mgr = cm_guard.as_ref().ok_or_else(|| {
+            tracing::warn!(
+                extension = %name,
+                "activate_channel_relay: channel manager not initialized"
+            );
             ExtensionError::ActivationFailed("Channel manager not initialized".to_string())
         })?;
 
-        channel_mgr
-            .hot_add(Box::new(channel))
-            .await
-            .map_err(|e| ExtensionError::ActivationFailed(e.to_string()))?;
+        channel_mgr.hot_add(Box::new(channel)).await.map_err(|e| {
+            tracing::warn!(
+                extension = %name,
+                error = %e,
+                "activate_channel_relay: hot_add to channel manager failed"
+            );
+            ExtensionError::ActivationFailed(e.to_string())
+        })?;
 
         if let Ok(mut cache) = self.relay_signing_secret_cache.lock() {
             *cache = Some(signing_secret);
+        } else {
+            tracing::warn!(
+                extension = %name,
+                "activate_channel_relay: failed to cache signing secret (mutex poisoned)"
+            );
         }
 
         // Store the event sender so the web gateway's relay webhook endpoint can push events
@@ -4316,6 +4576,12 @@ impl ExtensionManager {
         self.broadcast_extension_status(name, "active", Some(&status_msg))
             .await;
 
+        tracing::info!(
+            extension = %name,
+            instance_id = %instance_id,
+            "activate_channel_relay: relay channel activated successfully"
+        );
+
         Ok(ActivateResult {
             name: name.to_string(),
             kind: ExtensionKind::ChannelRelay,
@@ -4595,6 +4861,41 @@ impl ExtensionManager {
                 }
                 Ok(ExtensionSetupSchema { secrets, fields })
             }
+            ExtensionKind::ChannelRelay => {
+                let relay_url_key = format!("extensions.{name}.relay_url");
+                let current_url = if let Some(ref store) = self.store {
+                    match store.get_setting(&self.user_id, &relay_url_key).await {
+                        Ok(value_opt) => value_opt
+                            .and_then(|v| v.as_str().map(|s| s.to_string()))
+                            .filter(|s| !s.is_empty()),
+                        Err(e) => {
+                            tracing::warn!(
+                                extension = %name,
+                                setting_key = %relay_url_key,
+                                error = %e,
+                                "get_setup_schema: failed to read relay_url from settings"
+                            );
+                            None
+                        }
+                    }
+                } else {
+                    None
+                };
+                let env_url = self.relay_config.as_ref().map(|c| c.url.as_str());
+                Ok(ExtensionSetupSchema {
+                    secrets: Vec::new(),
+                    fields: vec![crate::channels::web::types::SetupFieldInfo {
+                        name: "relay_url".to_string(),
+                        prompt: format!(
+                            "Channel-relay service URL (leave empty to use env default{})",
+                            env_url.map(|u| format!(": {u}")).unwrap_or_default()
+                        ),
+                        optional: true,
+                        provided: current_url.is_some(),
+                        input_type: crate::tools::wasm::ToolSetupFieldInputType::Text,
+                    }],
+                })
+            }
             _ => Ok(ExtensionSetupSchema {
                 secrets: Vec::new(),
                 fields: Vec::new(),
@@ -4997,7 +5298,17 @@ impl ExtensionManager {
                 names.insert(server.token_secret_name());
                 (names, Vec::new())
             }
-            ExtensionKind::ChannelRelay => (std::collections::HashSet::new(), Vec::new()),
+            ExtensionKind::ChannelRelay => {
+                let relay_fields = vec![crate::tools::wasm::ToolFieldSetupSchema {
+                    name: "relay_url".to_string(),
+                    prompt: "Channel-relay service URL override".to_string(),
+                    optional: true,
+                    setting_path: Some(format!("extensions.{name}.relay_url")),
+                    input_type: crate::tools::wasm::ToolSetupFieldInputType::Text,
+                    restart_required: false,
+                }];
+                (std::collections::HashSet::new(), relay_fields)
+            }
         };
 
         let allowed_fields: std::collections::HashSet<String> =
@@ -5088,13 +5399,28 @@ impl ExtensionManager {
                 )));
             }
             let trimmed = field_value.trim();
+            let field_def = setup_field_defs.get(field_name);
+
+            // Empty value on an optional field with a setting_path: clear the
+            // stored override so the system reverts to the env/default value.
             if trimmed.is_empty() {
+                if let Some(def) = field_def
+                    && def.optional
+                {
+                    stored_fields.remove(field_name);
+                    if let Some(setting_path) = &def.setting_path {
+                        Self::validate_setup_setting_path(name, setting_path)?;
+                        if let Some(store) = self.store.as_ref() {
+                            let _ = store.delete_setting(&self.user_id, setting_path).await;
+                        }
+                    }
+                }
                 continue;
             }
 
             stored_fields.insert(field_name.clone(), trimmed.to_string());
 
-            if let Some(field_def) = setup_field_defs.get(field_name) {
+            if let Some(field_def) = field_def {
                 if field_def.restart_required {
                     restart_required = true;
                 }
@@ -7058,6 +7384,39 @@ mod tests {
         );
     }
 
+    /// Regression: installed-but-not-authenticated relay must NOT short-circuit
+    /// `auth_channel_relay()` to "authenticated".  Previously, `auth_channel_relay`
+    /// called `is_relay_channel()` which checked the in-memory
+    /// `installed_relay_extensions` set; that returned `true` even when no team_id
+    /// existed in the store, so the OAuth URL was never offered.
+    #[tokio::test]
+    async fn test_auth_channel_relay_installed_without_team_id_is_not_authenticated() {
+        let dir = tempfile::tempdir().expect("temp dir");
+        let mgr = make_test_manager(None, dir.path().to_path_buf());
+
+        // Mark as installed (simulates clicking Install in the UI)
+        mgr.installed_relay_extensions
+            .write()
+            .await
+            .insert("slack-relay".to_string());
+
+        // Without a stored team_id, auth should NOT return authenticated.
+        // It should fail because relay config is missing (no CHANNEL_RELAY_URL),
+        // but the key assertion is that it does NOT return Ok(authenticated).
+        let result = mgr.auth_channel_relay("slack-relay", "test").await;
+        match result {
+            Ok(ref auth_result) if auth_result.is_authenticated() => {
+                panic!(
+                    "auth_channel_relay returned authenticated for installed-but-no-team-id relay; \
+                     expected either an OAuth URL or a config error"
+                );
+            }
+            _ => {
+                // Config error (no relay URL) or awaiting_authorization — both are correct
+            }
+        }
+    }
+
     #[tokio::test]
     async fn test_remove_relay_shuts_down_via_relay_channel_manager() {
         // Regression: remove() only checked channel_runtime for shutdown, missing

src/extensions/mod.rs

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

src/llm/nearai_chat.rs

@@ -451,7 +451,7 @@ impl NearAiChatProvider {
             provider: "nearai_chat".to_string(),
             reason: format!(
                 "No model names found in response: {}",
-                &response_text[..response_text.len().min(300)]
+                &response_text[..crate::util::floor_char_boundary(&response_text, 300)]
             ),
         })
     }

src/llm/reasoning.rs

@@ -1017,11 +1017,8 @@ Example:
 
         "\n\n## Extensions\n\
          You can search, install, and activate extensions to add new capabilities:\n\
-         - **Channels** (Telegram, Slack, Discord) — connect messaging platforms so users can \
-         talk to you there. When users ask about connecting a messaging platform, search for it \
-         as a channel. Channels are not separate send-message tools; use normal assistant output \
-         to reply in the current conversation, and use the `message` tool only for proactive, \
-         background, or cross-channel outbound sends.\n\
+         - **Channels** (Telegram, Slack, Discord) — messaging integrations. \
+         When users ask about connecting a messaging platform, search for it as a channel.\n\
          - **Tools** — sandboxed functions that extend your abilities.\n\
          - **MCP servers** — external API integrations via the Model Context Protocol.\n\n\
          Use `tool_search` to find extensions by name. Refer to them by their kind \
@@ -1062,20 +1059,15 @@ Example:
 
         let message_tool_hint = "\
 \n\n## Proactive Messaging\n\
-For ordinary replies in the current conversation, respond normally without calling `message`.\n\
 Send messages via Signal, Telegram, Slack, or other connected channels:\n\
 - `content` (required): the message text\n\
 - `attachments` (optional): array of file paths to send\n\
 - `channel` (optional): which channel to use (signal, telegram, slack, etc.)\n\
 - `target` (optional): who to send to (phone number, group ID, etc.)\n\
-\nOmit both `channel` and `target` for a proactive follow-up in the current conversation.\n\
-Target formats:\n\
-- Signal: E.164 phone number (`+1234567890`) or group ID\n\
-- Telegram: username or chat ID\n\
-- Slack: channel name (`#general`) or user ID\n\
+\nOmit both `channel` and `target` to send to the current conversation.\n\
 Examples (tool calls use JSON format):\n\
-- Proactive follow-up here: {\"content\": \"Hi again!\"}\n\
-- Send file here proactively: {\"content\": \"Here's the file\", \"attachments\": [\"/path/to/file.txt\"]}\n\
+- Reply here: {\"content\": \"Hi!\"}\n\
+- Send file here: {\"content\": \"Here's the file\", \"attachments\": [\"/path/to/file.txt\"]}\n\
 - Message a different user: {\"channel\": \"signal\", \"target\": \"+1234567890\", \"content\": \"Hi!\"}\n\
 - Message a different group: {\"channel\": \"signal\", \"target\": \"group:abc123\", \"content\": \"Hi!\"}";
 
@@ -1113,9 +1105,7 @@ Examples (tool calls use JSON format):\n\
 
         format!(
             "\n\n## Current Conversation\n\
-             This is who you're talking to in the active conversation. Use normal assistant \
-             output to reply here; only use the `message` tool for proactive, background, or \
-             cross-channel outbound sends:\n{}",
+             This is who you're talking to (omit 'target' to send here):\n{}",
             lines.join("\n")
         )
     }
@@ -2462,54 +2452,6 @@ That's my plan."#;
         );
     }
 
-    #[test]
-    fn test_extensions_section_clarifies_channels_are_not_send_tools() {
-        let reasoning = make_test_reasoning();
-        let tool_defs = vec![ToolDefinition {
-            name: "tool_search".to_string(),
-            description: "Search extensions".to_string(),
-            parameters: serde_json::json!({}),
-        }];
-
-        let section = reasoning.build_extensions_section_for_tools(&tool_defs);
-        assert!(section.contains("connect messaging platforms so users can talk to you there"));
-        assert!(section.contains("Channels are not separate send-message tools"));
-        assert!(
-            section.contains("use normal assistant output to reply in the current conversation")
-        );
-        assert!(section.contains(
-            "`message` tool only for proactive, background, or cross-channel outbound sends"
-        ));
-    }
-
-    #[test]
-    fn test_channel_section_separates_normal_replies_from_message_tool() {
-        let reasoning = make_test_reasoning().with_channel("telegram");
-
-        let section = reasoning.build_channel_section();
-        assert!(section.contains("respond normally without calling `message`"));
-        assert!(section.contains("proactive follow-up in the current conversation"));
-        assert!(section.contains("Target formats:"));
-        assert!(section.contains("Signal: E.164 phone number"));
-        assert!(section.contains("Telegram: username or chat ID"));
-        assert!(section.contains("Slack: channel name"));
-        assert!(section.contains("Proactive follow-up here"));
-    }
-
-    #[test]
-    fn test_current_conversation_section_does_not_imply_message_tool_for_replies() {
-        let reasoning = make_test_reasoning()
-            .with_channel("telegram")
-            .with_conversation_data("User", "telegram-user");
-
-        let section = reasoning.build_conversation_section();
-        assert!(section.contains("Use normal assistant output to reply here"));
-        assert!(section.contains(
-            "only use the `message` tool for proactive, background, or cross-channel outbound sends"
-        ));
-        assert!(!section.contains("omit 'target' to send here"));
-    }
-
     // ---- plan/evaluate bypass clean_response (Bug #564-2) ----
 
     #[test]

src/tools/builtin/extension_tools.rs

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

src/tools/builtin/message.rs

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

src/tools/builtin/routine.rs

@@ -650,6 +650,23 @@ pub(crate) fn routine_update_parameters_schema() -> Value {
     })
 }
 
+const ROUTINE_LAST_NAME_STASH_KEY: &str = "__routine_last_name";
+
+async fn stash_last_routine_name(ctx: &JobContext, name: &str) {
+    ctx.tool_output_stash
+        .write()
+        .await
+        .insert(ROUTINE_LAST_NAME_STASH_KEY.to_string(), name.to_string());
+}
+
+async fn restore_last_routine_name(ctx: &JobContext) -> Option<String> {
+    ctx.tool_output_stash
+        .read()
+        .await
+        .get(ROUTINE_LAST_NAME_STASH_KEY)
+        .cloned()
+}
+
 fn nested_object<'a>(params: &'a Value, field: &str) -> Option<&'a Map<String, Value>> {
     params.get(field).and_then(Value::as_object)
 }
@@ -1093,6 +1110,7 @@ impl Tool for RoutineCreateTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
         let normalized = parse_routine_create_request(&params)?;
+        stash_last_routine_name(ctx, &normalized.name).await;
         let trigger = build_routine_trigger(&normalized.trigger);
         let action =
             build_routine_action(&normalized.name, &normalized.prompt, &normalized.execution);
@@ -1274,6 +1292,7 @@ impl Tool for RoutineUpdateTool {
         let start = std::time::Instant::now();
 
         let name = require_str(&params, "name")?;
+        stash_last_routine_name(ctx, name).await;
 
         let mut routine = self
             .store
@@ -1411,11 +1430,24 @@ impl Tool for RoutineDeleteTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let name = require_str(&params, "name")?;
+        let name = if let Some(name) = params.get("name").and_then(|v| v.as_str()) {
+            if name.trim().is_empty() {
+                return Err(ToolError::InvalidParameters(
+                    "'name' parameter cannot be empty".to_string(),
+                ));
+            }
+            name.to_string()
+        } else {
+            restore_last_routine_name(ctx).await.ok_or_else(|| {
+                ToolError::InvalidParameters(
+                    "missing 'name' parameter and no previous routine target to infer".to_string(),
+                )
+            })?
+        };
 
         let routine = self
             .store
-            .get_routine_by_name(&ctx.user_id, name)
+            .get_routine_by_name(&ctx.user_id, &name)
             .await
             .map_err(|e| ToolError::ExecutionFailed(format!("DB error: {e}")))?
             .ok_or_else(|| ToolError::ExecutionFailed(format!("routine '{}' not found", name)))?;
@@ -1430,7 +1462,7 @@ impl Tool for RoutineDeleteTool {
         self.engine.refresh_event_cache().await;
 
         let result = serde_json::json!({
-            "name": name,
+            "name": &name,
             "deleted": deleted,
         });
 

src/tools/mcp/client.rs

@@ -117,6 +117,11 @@ impl McpClient {
     /// The config must use HTTP transport (the default); for stdio/UDS use `new_with_transport`.
     ///
     /// Returns an error if the config uses a non-HTTP transport.
+    ///
+    /// **Note:** The session manager is NOT wired into the transport. For
+    /// production use, prefer `create_client_from_config()` which constructs
+    /// the transport with session tracking.
+    #[cfg(test)]
     pub fn new_with_config(config: McpServerConfig) -> Result<Self, ToolError> {
         if !matches!(
             config.effective_transport(),
@@ -214,7 +219,14 @@ impl McpClient {
         }
     }
 
-    /// Attach a session manager for Streamable HTTP session tracking.
+    /// Attach a session manager to the **client** only.
+    ///
+    /// **Warning:** This does NOT wire the session manager into the underlying
+    /// `HttpMcpTransport`, so the transport will not capture `Mcp-Session-Id`
+    /// from responses. For production use, construct the transport with
+    /// `HttpMcpTransport::with_session_manager()` and pass it to
+    /// `new_with_transport()` instead. See `create_client_from_config()`.
+    #[cfg(test)]
     pub fn with_session_manager(mut self, session_manager: Arc<McpSessionManager>) -> Self {
         self.session_manager = Some(session_manager);
         self
@@ -235,6 +247,12 @@ impl McpClient {
         self.session_manager.is_some()
     }
 
+    /// Get the underlying transport (test-only).
+    #[cfg(test)]
+    pub(crate) fn transport(&self) -> &Arc<dyn McpTransport> {
+        &self.transport
+    }
+
     /// Get the next request ID.
     fn next_request_id(&self) -> u64 {
         self.next_id.fetch_add(1, Ordering::SeqCst)

src/tools/mcp/factory.rs

@@ -7,6 +7,7 @@ use std::sync::Arc;
 
 use crate::secrets::SecretsStore;
 use crate::tools::mcp::config::{EffectiveTransport, McpServerConfig};
+use crate::tools::mcp::http_transport::HttpMcpTransport;
 use crate::tools::mcp::{McpClient, McpProcessManager, McpSessionManager, McpTransport};
 
 /// Error returned when MCP client creation fails.
@@ -78,33 +79,37 @@ pub async fn create_client_from_config(
             Err(McpFactoryError::UnixNotSupported { name: server_name })
         }
         EffectiveTransport::Http => {
+            // Authenticated (OAuth) path: tokens exist or server requires auth.
             if let Some(ref secrets) = secrets {
                 let has_tokens =
                     crate::tools::mcp::is_authenticated(&server, secrets, user_id).await;
 
                 if has_tokens || server.requires_auth() {
-                    Ok(McpClient::new_authenticated(
+                    return Ok(McpClient::new_authenticated(
                         server,
                         Arc::clone(session_manager),
                         Arc::clone(secrets),
                         user_id,
-                    ))
-                } else {
-                    Ok(McpClient::new_with_config(server)
-                        .map_err(|e| McpFactoryError::InvalidConfig {
-                            name: server_name.clone(),
-                            reason: e.to_string(),
-                        })?
-                        .with_session_manager(Arc::clone(session_manager)))
+                    ));
                 }
-            } else {
-                Ok(McpClient::new_with_config(server)
-                    .map_err(|e| McpFactoryError::InvalidConfig {
-                        name: server_name,
-                        reason: e.to_string(),
-                    })?
-                    .with_session_manager(Arc::clone(session_manager)))
             }
+
+            // Non-OAuth HTTP: wire the session manager into the *transport* so
+            // it captures `Mcp-Session-Id` from responses. Passing it only to
+            // the client (via `with_session_manager`) is not enough — the
+            // transport must know about it to read/write the header.
+            let transport = Arc::new(
+                HttpMcpTransport::new(server.url.clone(), server.name.clone())
+                    .with_session_manager(Arc::clone(session_manager)),
+            );
+            Ok(McpClient::new_with_transport(
+                server.name.clone(),
+                transport,
+                Some(Arc::clone(session_manager)),
+                secrets,
+                user_id,
+                Some(server),
+            ))
         }
     }
 }
@@ -134,4 +139,84 @@ mod tests {
             "non-OAuth HTTP clients must carry a session manager"
         );
     }
+
+    /// Regression test: the factory must wire the session manager into the
+    /// *transport*, not just the client. Otherwise the transport never
+    /// captures `Mcp-Session-Id` from responses and subsequent requests
+    /// lack the header, causing the server to reject them.
+    #[tokio::test]
+    async fn test_factory_non_oauth_http_transport_captures_session_id() {
+        use axum::http::header::HeaderName;
+        use axum::{Router, http::StatusCode, response::IntoResponse, routing::post};
+        use tokio::net::TcpListener;
+
+        const SESSION_ID: &str = "test-session-abc123";
+
+        async fn session_echo() -> impl IntoResponse {
+            let body = serde_json::json!({
+                "jsonrpc": "2.0",
+                "id": 1,
+                "result": {}
+            })
+            .to_string();
+            (
+                StatusCode::OK,
+                [(
+                    HeaderName::from_static("mcp-session-id"),
+                    SESSION_ID.to_string(),
+                )],
+                body,
+            )
+        }
+
+        let app = Router::new().route("/", post(session_echo));
+        let listener = TcpListener::bind("127.0.0.1:0").await.unwrap();
+        let addr = listener.local_addr().unwrap();
+        let url = format!("http://127.0.0.1:{}", addr.port());
+
+        tokio::spawn(async move {
+            axum::serve(listener, app).await.unwrap();
+        });
+
+        let server = McpServerConfig::new("session-test", &url);
+        let session_manager = Arc::new(McpSessionManager::new());
+        let process_manager = Arc::new(McpProcessManager::new());
+
+        let client = create_client_from_config(
+            server,
+            &session_manager,
+            &process_manager,
+            None,
+            "test-user",
+        )
+        .await
+        .expect("factory should succeed for HTTP config");
+
+        // Pre-create a session entry so that update_session_id has something to update.
+        // In production, the MCP initialize handshake calls get_or_create before responses arrive.
+        session_manager.get_or_create("session-test", &url).await;
+
+        // Send a request through the client's transport to trigger session capture.
+        use crate::tools::mcp::protocol::McpRequest;
+        let request = McpRequest {
+            jsonrpc: "2.0".to_string(),
+            id: Some(1),
+            method: "test".to_string(),
+            params: Some(serde_json::json!({})),
+        };
+        let headers = std::collections::HashMap::new();
+        client
+            .transport()
+            .send(&request, &headers)
+            .await
+            .expect("request should succeed");
+
+        // Verify the session manager captured the session ID from the response.
+        let captured = session_manager.get_session_id("session-test").await;
+        assert_eq!(
+            captured.as_deref(),
+            Some(SESSION_ID),
+            "transport must capture Mcp-Session-Id into session manager"
+        );
+    }
 }

src/tools/mcp/http_transport.rs

@@ -494,6 +494,34 @@ mod tests {
         assert_eq!(echoed["authorization"], "Bearer oauth-token");
     }
 
+    /// Regression test for #1436: 202 Accepted responses for notifications
+    /// were parsed as JSON, causing "Failed to parse MCP response" errors
+    /// that broke the MCP session handshake.
+    #[tokio::test]
+    async fn test_wire_202_accepted_for_notification() {
+        use axum::{Router, http::StatusCode, routing::post};
+        use tokio::net::TcpListener;
+
+        async fn accept_notification() -> StatusCode {
+            StatusCode::ACCEPTED
+        }
+
+        let app = Router::new().route("/", post(accept_notification));
+        let listener = TcpListener::bind("127.0.0.1:0").await.unwrap();
+        let addr = listener.local_addr().unwrap();
+        let url = format!("http://127.0.0.1:{}", addr.port());
+
+        tokio::spawn(async move {
+            axum::serve(listener, app).await.unwrap();
+        });
+
+        let transport = HttpMcpTransport::new(&url, "test-202");
+        let request = McpRequest::initialized_notification();
+        let response = transport.send(&request, &HashMap::new()).await.unwrap();
+        assert!(response.result.is_none());
+        assert!(response.error.is_none());
+    }
+
     #[tokio::test]
     async fn test_wire_custom_auth_preserved_when_no_per_request_auth() {
         let (url, _handle) = spawn_echo_server().await;

tests/e2e_builtin_tool_coverage.rs

@@ -13,7 +13,7 @@ mod tests {
     use ironclaw::agent::routine::{RoutineAction, Trigger};
 
     use crate::support::test_rig::TestRigBuilder;
-    use crate::support::trace_llm::{LlmTrace, TraceResponse, TraceStep, TraceToolCall, TraceTurn};
+    use crate::support::trace_llm::LlmTrace;
 
     // -----------------------------------------------------------------------
     // Test 1: time_parse_and_diff
@@ -205,7 +205,44 @@ mod tests {
     }
 
     // -----------------------------------------------------------------------
-    // Test 5: routine_manual_create_defaults_to_tools_enabled
+    // Test 5: routine_update_fail_delete_fallback
+    // -----------------------------------------------------------------------
+
+    #[tokio::test]
+    async fn routine_update_fail_delete_fallback() {
+        let trace = LlmTrace::from_file(concat!(
+            env!("CARGO_MANIFEST_DIR"),
+            "/tests/fixtures/llm_traces/tools/routine_update_fail_delete_fallback.json"
+        ))
+        .expect("failed to load routine_update_fail_delete_fallback.json");
+
+        let rig = TestRigBuilder::new()
+            .with_trace(trace.clone())
+            .with_auto_approve_tools(true)
+            .build()
+            .await;
+
+        rig.send_message("Try converting a routine trigger, then recover by deleting it")
+            .await;
+        let responses = rig.wait_for_responses(1, Duration::from_secs(15)).await;
+
+        rig.verify_trace_expects(&trace, &responses);
+
+        let completed = rig.tool_calls_completed();
+        assert!(
+            completed.iter().any(|(n, ok)| n == "routine_update" && !ok),
+            "routine_update should fail in this regression path: {completed:?}"
+        );
+        assert!(
+            completed.iter().any(|(n, ok)| n == "routine_delete" && *ok),
+            "routine_delete should recover successfully via preserved routine identity: {completed:?}"
+        );
+
+        rig.shutdown();
+    }
+
+    // -----------------------------------------------------------------------
+    // Test 6: routine_manual_create_defaults_to_tools_enabled
     // -----------------------------------------------------------------------
 
     #[tokio::test]
@@ -246,7 +283,7 @@ mod tests {
     }
 
     // -----------------------------------------------------------------------
-    // Test 6: routine_manual_create_explicit_no_tools
+    // Test 7: routine_manual_create_explicit_no_tools
     // -----------------------------------------------------------------------
 
     #[tokio::test]
@@ -287,7 +324,7 @@ mod tests {
     }
 
     // -----------------------------------------------------------------------
-    // Test 7: routine_history
+    // Test 8: routine_history
     // -----------------------------------------------------------------------
 
     #[tokio::test]
@@ -838,112 +875,4 @@ mod tests {
 
         rig.shutdown();
     }
-
-    #[tokio::test]
-    async fn tool_info_clarifies_message_and_channel_setup_roles() {
-        let trace = LlmTrace::new(
-            "test-tool-info-channel-message-clarity",
-            vec![TraceTurn {
-                user_input: "How do message and channels differ?".to_string(),
-                steps: vec![
-                    TraceStep {
-                        request_hint: None,
-                        response: TraceResponse::ToolCalls {
-                            tool_calls: vec![TraceToolCall {
-                                id: "call_tool_info_message".to_string(),
-                                name: "tool_info".to_string(),
-                                arguments: serde_json::json!({"name": "message"}),
-                            }],
-                            input_tokens: 100,
-                            output_tokens: 20,
-                        },
-                        expected_tool_results: Vec::new(),
-                    },
-                    TraceStep {
-                        request_hint: None,
-                        response: TraceResponse::ToolCalls {
-                            tool_calls: vec![TraceToolCall {
-                                id: "call_tool_info_tool_search".to_string(),
-                                name: "tool_info".to_string(),
-                                arguments: serde_json::json!({"name": "tool_search"}),
-                            }],
-                            input_tokens: 140,
-                            output_tokens: 20,
-                        },
-                        expected_tool_results: Vec::new(),
-                    },
-                    TraceStep {
-                        request_hint: None,
-                        response: TraceResponse::Text {
-                            content: "I checked both tool descriptions.".to_string(),
-                            input_tokens: 220,
-                            output_tokens: 30,
-                        },
-                        expected_tool_results: Vec::new(),
-                    },
-                ],
-                expects: Default::default(),
-            }],
-        );
-
-        let rig = TestRigBuilder::new()
-            .with_trace(trace.clone())
-            .with_auto_approve_tools(true)
-            .build()
-            .await;
-
-        rig.send_message("How do message and channels differ?")
-            .await;
-        let responses = rig.wait_for_responses(1, Duration::from_secs(15)).await;
-
-        rig.verify_trace_expects(&trace, &responses);
-
-        let results = rig.tool_results();
-        let info_results: Vec<_> = results.iter().filter(|(n, _)| n == "tool_info").collect();
-        assert_eq!(info_results.len(), 2, "Expected two tool_info results");
-
-        let info_json: Vec<serde_json::Value> = info_results
-            .iter()
-            .map(|(_, preview)| {
-                serde_json::from_str(preview)
-                    .expect("tool_info result preview should be valid JSON")
-            })
-            .collect();
-
-        let message_json = info_json
-            .iter()
-            .find(|info| info["name"] == "message")
-            .expect("tool_info result should contain 'message'");
-        let message_description = message_json["description"]
-            .as_str()
-            .expect("message description should be a string");
-        assert!(
-            message_description.contains("Use normal assistant output to reply"),
-            "message description should distinguish normal replies: {message_description}"
-        );
-        assert!(
-            message_description.contains("proactive notifications"),
-            "message description should describe proactive sends: {message_description}"
-        );
-
-        let tool_search_json = info_json
-            .iter()
-            .find(|info| info["name"] == "tool_search")
-            .expect("tool_info result should contain 'tool_search'");
-        let tool_search_description = tool_search_json["description"]
-            .as_str()
-            .expect("tool_search description should be a string");
-        assert!(
-            tool_search_description.contains("`tool_install`")
-                && tool_search_description.contains("`tool_activate`"),
-            "tool_search description should describe setup/activation via tool_install and \
-             tool_activate: {tool_search_description}"
-        );
-        assert!(
-            tool_search_description.contains("use the `message` tool for proactive outbound sends"),
-            "tool_search description should point outbound sends to message: {tool_search_description}"
-        );
-
-        rig.shutdown();
-    }
 }

tests/fixtures/llm_traces/tools/routine_update_fail_delete_fallback.json

@@ -0,0 +1,70 @@
+{
+  "model_name": "test-routine-update-fail-delete-fallback",
+  "expects": {
+    "tools_used": ["routine_create", "routine_update", "routine_delete"],
+    "tool_results_contain": {
+      "routine_update": "Cannot update schedule or timezone on a non-cron routine.",
+      "routine_delete": "temp-routine"
+    },
+    "min_responses": 1
+  },
+  "steps": [
+    {
+      "response": {
+        "type": "tool_calls",
+        "tool_calls": [
+          {
+            "id": "call_rc_fallback",
+            "name": "routine_create",
+            "arguments": {
+              "name": "temp-routine",
+              "trigger_type": "manual",
+              "prompt": "Temporary routine for fallback test."
+            }
+          }
+        ],
+        "input_tokens": 120,
+        "output_tokens": 40
+      }
+    },
+    {
+      "response": {
+        "type": "tool_calls",
+        "tool_calls": [
+          {
+            "id": "call_ru_fallback",
+            "name": "routine_update",
+            "arguments": {
+              "name": "temp-routine",
+              "schedule": "0 */10 * * * *"
+            }
+          }
+        ],
+        "input_tokens": 200,
+        "output_tokens": 30
+      }
+    },
+    {
+      "response": {
+        "type": "tool_calls",
+        "tool_calls": [
+          {
+            "id": "call_rd_fallback",
+            "name": "routine_delete",
+            "arguments": {}
+          }
+        ],
+        "input_tokens": 300,
+        "output_tokens": 20
+      }
+    },
+    {
+      "response": {
+        "type": "text",
+        "content": "I recovered from the failed update and cleaned up the original routine.",
+        "input_tokens": 380,
+        "output_tokens": 25
+      }
+    }
+  ]
+}

tests/multi_tenant_system_prompt.rs

@@ -237,47 +237,4 @@ mod tests {
 
         rig.shutdown();
     }
-
-    #[tokio::test]
-    async fn telegram_system_prompt_clarifies_reply_vs_proactive_message_tool() {
-        let trace = simple_trace(1);
-        let rig = TestRigBuilder::new().with_trace(trace).build().await;
-
-        let msg = IncomingMessage::new("telegram", "telegram-user", "Hello there");
-        rig.send_incoming(msg).await;
-        let _responses = rig.wait_for_responses(1, TIMEOUT).await;
-
-        let requests = rig.captured_llm_requests();
-        let system_prompt =
-            extract_system_prompt(&requests).expect("Expected a system prompt in the LLM request");
-
-        assert!(
-            system_prompt.contains("Channels are not separate send-message tools"),
-            "System prompt should describe channels as setup/integration surfaces.\n\
-             Actual system prompt:\n{system_prompt}"
-        );
-        assert!(
-            system_prompt
-                .contains("use normal assistant output to reply in the current conversation"),
-            "System prompt should route ordinary replies through normal assistant output.\n\
-             Actual system prompt:\n{system_prompt}"
-        );
-        assert!(
-            system_prompt.contains("respond normally without calling `message`"),
-            "System prompt should say normal replies do not use the message tool.\n\
-             Actual system prompt:\n{system_prompt}"
-        );
-        assert!(
-            system_prompt.contains("proactive follow-up in the current conversation"),
-            "System prompt should reserve omitted channel/target for proactive follow-ups.\n\
-             Actual system prompt:\n{system_prompt}"
-        );
-        assert!(
-            !system_prompt.contains("omit 'target' to send here"),
-            "System prompt should not imply the message tool is the default way to reply \
-             in-thread.\nActual system prompt:\n{system_prompt}"
-        );
-
-        rig.shutdown();
-    }
 }