Format prompt guidance assertions

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

CHANGELOG.md

@@ -7,24 +7,6 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ## [Unreleased]
 
-## [0.23.0](https://github.com/nearai/ironclaw/compare/ironclaw-v0.22.0...ironclaw-v0.23.0) - 2026-03-27
-
-### Added
-
-- complete multi-tenant isolation — phases 2–4 ([#1614](https://github.com/nearai/ironclaw/pull/1614))
-
-### Fixed
-
-- *(routines)* recover delete name after failed update fallback ([#1108](https://github.com/nearai/ironclaw/pull/1108))
-- *(mcp)* handle 202 Accepted and wire session manager for Streamable HTTP ([#1437](https://github.com/nearai/ironclaw/pull/1437))
-- *(extensions)* channel-relay auth dead-end, observability, and URL override ([#1681](https://github.com/nearai/ironclaw/pull/1681))
-- *(agent)* discard truncated tool calls when finish_reason == Length ([#1631](https://github.com/nearai/ironclaw/pull/1631)) ([#1632](https://github.com/nearai/ironclaw/pull/1632))
-- *(llm)* filter XML tool-call recovery by context ([#1641](https://github.com/nearai/ironclaw/pull/1641))
-
-### Other
-
-- Support direct hosted OAuth callbacks with proxy auth token ([#1684](https://github.com/nearai/ironclaw/pull/1684))
-
 ## [0.22.0](https://github.com/nearai/ironclaw/compare/ironclaw-v0.21.0...ironclaw-v0.22.0) - 2026-03-25
 
 ### Added

Cargo.lock

@@ -3390,7 +3390,7 @@ dependencies = [
 
 [[package]]
 name = "ironclaw"
-version = "0.23.0"
+version = "0.22.0"
 dependencies = [
  "aes-gcm",
  "aho-corasick",

Cargo.toml

@@ -20,7 +20,7 @@ exclude = [
 
 [package]
 name = "ironclaw"
-version = "0.23.0"
+version = "0.22.0"
 edition = "2024"
 rust-version = "1.92"
 description = "Secure personal AI assistant that protects your data and expands its capabilities on the fly"

src/channels/relay/client.rs

@@ -122,32 +122,18 @@ 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(&url)
+            .get(format!("{}/oauth/slack/auth", self.base_url))
             .bearer_auth(self.api_key.expose_secret())
             .query(&query)
             .send()
             .await
-            .map_err(|e| {
+            .map_err(|e| RelayError::Network(e.to_string()))?;
-                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() {
@@ -238,39 +224,20 @@ 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(&url)
+            .post(format!("{}/proxy/{}/{}", self.base_url, provider, method))
             .bearer_auth(self.api_key.expose_secret())
             .query(&query)
             .json(&body)
             .send()
             .await
-            .map_err(|e| {
+            .map_err(|e| RelayError::Network(e.to_string()))?;
-                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,
@@ -288,45 +255,23 @@ 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(&url)
+            .get(format!("{}/relay/signing-secret", self.base_url))
             .bearer_auth(self.api_key.expose_secret())
             .query(&[("team_id", team_id)])
             .send()
             .await
-            .map_err(|e| {
+            .map_err(|e| RelayError::Network(e.to_string()))?;
-                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

@@ -836,10 +836,10 @@ async fn oauth_callback_handler(
 
     let result: Result<(), String> = async {
         let token_response = if let Some(proxy_url) = &exchange_proxy_url {
-            let oauth_proxy_auth_token = flow.oauth_proxy_auth_token().unwrap_or_default();
+            let gateway_token = flow.gateway_token.as_deref().unwrap_or_default();
             oauth_defaults::exchange_via_proxy(oauth_defaults::ProxyTokenExchangeRequest {
                 proxy_url,
-                gateway_token: oauth_proxy_auth_token,
+                gateway_token,
                 token_url: &flow.token_url,
                 client_id: &flow.client_id,
                 client_secret: flow.client_secret.as_deref(),
@@ -1177,31 +1177,11 @@ async fn slack_relay_oauth_callback_handler(
 
         // Store team_id in settings
         let team_id_key = format!("relay:{}:team_id", DEFAULT_RELAY_NAME);
-        tracing::info!(
+        let _ = store
-            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
@@ -2201,11 +2181,6 @@ async fn extensions_activate_handler(
     AuthenticatedUser(user): AuthenticatedUser,
     Path(name): Path<String>,
 ) -> Result<Json<ActionResponse>, (StatusCode, String)> {
-    tracing::debug!(
-        extension = %name,
-        user_id = %user.user_id,
-        "extensions_activate_handler: received activate request"
-    );
     let ext_mgr = state.extension_manager.as_ref().ok_or((
         StatusCode::NOT_IMPLEMENTED,
         "Extension manager not available (secrets store required)".to_string(),
@@ -2213,10 +2188,6 @@ 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).
@@ -2235,13 +2206,6 @@ 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())));
             }
@@ -2249,21 +2213,10 @@ 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) => {
+                        Err(e) => Ok(Json(ActionResponse::fail(e.to_string()))),
-                            tracing::warn!(
-                                extension = %name,
-                                error = %e,
-                                "extensions_activate_handler: retry after auth still failed"
-                            );
-                            Ok(Json(ActionResponse::fail(e.to_string())))
-                        }
                     }
                 }
                 Ok(auth_result) => {
@@ -3057,160 +3010,6 @@ mod tests {
             .with_state(state)
     }
 
-    #[derive(Clone, Debug)]
-    struct RecordedOauthProxyRequest {
-        authorization: Option<String>,
-        form: std::collections::HashMap<String, String>,
-    }
-
-    #[derive(Clone)]
-    struct MockOauthProxyState {
-        requests: Arc<tokio::sync::Mutex<Vec<RecordedOauthProxyRequest>>>,
-    }
-
-    struct MockOauthProxyServer {
-        addr: std::net::SocketAddr,
-        requests: Arc<tokio::sync::Mutex<Vec<RecordedOauthProxyRequest>>>,
-        shutdown_tx: Option<tokio::sync::oneshot::Sender<()>>,
-        server_task: Option<tokio::task::JoinHandle<()>>,
-    }
-
-    impl MockOauthProxyServer {
-        async fn start() -> Self {
-            async fn exchange_handler(
-                State(state): State<MockOauthProxyState>,
-                headers: axum::http::HeaderMap,
-                axum::Form(form): axum::Form<std::collections::HashMap<String, String>>,
-            ) -> Json<serde_json::Value> {
-                state.requests.lock().await.push(RecordedOauthProxyRequest {
-                    authorization: headers
-                        .get(axum::http::header::AUTHORIZATION)
-                        .and_then(|value| value.to_str().ok())
-                        .map(str::to_string),
-                    form,
-                });
-                Json(serde_json::json!({
-                    "access_token": "proxy-access-token",
-                    "refresh_token": "proxy-refresh-token",
-                    "expires_in": 7200
-                }))
-            }
-
-            let requests = Arc::new(tokio::sync::Mutex::new(Vec::new()));
-            let listener = tokio::net::TcpListener::bind("127.0.0.1:0")
-                .await
-                .expect("bind mock oauth proxy");
-            let addr = listener.local_addr().expect("mock oauth proxy addr");
-            let app = Router::new()
-                .route("/oauth/exchange", post(exchange_handler))
-                .with_state(MockOauthProxyState {
-                    requests: Arc::clone(&requests),
-                });
-            let (shutdown_tx, shutdown_rx) = tokio::sync::oneshot::channel::<()>();
-            let server_task = tokio::spawn(async move {
-                let _ = axum::serve(listener, app)
-                    .with_graceful_shutdown(async {
-                        let _ = shutdown_rx.await;
-                    })
-                    .await;
-            });
-
-            Self {
-                addr,
-                requests,
-                shutdown_tx: Some(shutdown_tx),
-                server_task: Some(server_task),
-            }
-        }
-
-        fn base_url(&self) -> String {
-            format!("http://{}", self.addr)
-        }
-
-        async fn requests(&self) -> Vec<RecordedOauthProxyRequest> {
-            self.requests.lock().await.clone()
-        }
-
-        async fn shutdown(mut self) {
-            if let Some(tx) = self.shutdown_tx.take() {
-                let _ = tx.send(());
-            }
-            if let Some(task) = self.server_task.take() {
-                let _ = task.await;
-            }
-        }
-    }
-
-    impl Drop for MockOauthProxyServer {
-        fn drop(&mut self) {
-            if let Some(tx) = self.shutdown_tx.take() {
-                let _ = tx.send(());
-            }
-            if let Some(task) = self.server_task.take() {
-                task.abort();
-            }
-        }
-    }
-
-    struct EnvVarGuard {
-        key: &'static str,
-        original: Option<String>,
-    }
-
-    impl Drop for EnvVarGuard {
-        fn drop(&mut self) {
-            // SAFETY: Tests use lock_env() to serialize environment access.
-            unsafe {
-                if let Some(ref value) = self.original {
-                    std::env::set_var(self.key, value);
-                } else {
-                    std::env::remove_var(self.key);
-                }
-            }
-        }
-    }
-
-    fn set_env_var(key: &'static str, value: Option<&str>) -> EnvVarGuard {
-        let original = std::env::var(key).ok();
-        // SAFETY: Tests use lock_env() to serialize environment access.
-        unsafe {
-            if let Some(value) = value {
-                std::env::set_var(key, value);
-            } else {
-                std::env::remove_var(key);
-            }
-        }
-        EnvVarGuard { key, original }
-    }
-
-    fn fresh_pending_oauth_flow(
-        secrets: Arc<dyn crate::secrets::SecretsStore + Send + Sync>,
-        sse_manager: Option<Arc<SseManager>>,
-        oauth_proxy_auth_token: Option<String>,
-    ) -> crate::cli::oauth_defaults::PendingOAuthFlow {
-        crate::cli::oauth_defaults::PendingOAuthFlow {
-            extension_name: "test_tool".to_string(),
-            display_name: "Test Tool".to_string(),
-            token_url: "https://example.com/token".to_string(),
-            client_id: "client123".to_string(),
-            client_secret: None,
-            redirect_uri: "https://example.com/oauth/callback".to_string(),
-            code_verifier: Some("test-code-verifier".to_string()),
-            access_token_field: "access_token".to_string(),
-            secret_name: "test_token".to_string(),
-            provider: Some("google".to_string()),
-            validation_endpoint: None,
-            scopes: vec!["email".to_string()],
-            user_id: "test".to_string(),
-            secrets,
-            sse_manager,
-            gateway_token: oauth_proxy_auth_token,
-            token_exchange_extra_params: std::collections::HashMap::new(),
-            client_id_secret_name: None,
-            created_at: std::time::Instant::now(),
-        }
-    }
-
     #[tokio::test]
     async fn test_extensions_setup_submit_returns_failure_when_not_activated() {
         use axum::body::Body;
@@ -3868,284 +3667,6 @@ mod tests {
         );
     }
 
-    #[tokio::test]
-    async fn test_oauth_callback_accepts_versioned_hosted_state_without_instance_name() {
-        use axum::body::Body;
-        use tower::ServiceExt;
-
-        let secrets: Arc<dyn crate::secrets::SecretsStore + Send + Sync> =
-            Arc::new(crate::secrets::InMemorySecretsStore::new(Arc::new(
-                crate::secrets::SecretsCrypto::new(secrecy::SecretString::from(
-                    TEST_GATEWAY_CRYPTO_KEY.to_string(),
-                ))
-                .expect("crypto"),
-            )));
-        let (ext_mgr, _wasm_tools_dir, _wasm_channels_dir) = test_ext_mgr(secrets.clone());
-
-        let Some(created_at) = expired_flow_created_at() else {
-            eprintln!(
-                "Skipping versioned OAuth state without instance test: monotonic uptime below expiry window"
-            );
-            return;
-        };
-        let flow = crate::cli::oauth_defaults::PendingOAuthFlow {
-            extension_name: "test_tool".to_string(),
-            display_name: "Test Tool".to_string(),
-            token_url: "https://example.com/token".to_string(),
-            client_id: "client123".to_string(),
-            client_secret: None,
-            redirect_uri: "https://example.com/oauth/callback".to_string(),
-            code_verifier: None,
-            access_token_field: "access_token".to_string(),
-            secret_name: "test_token".to_string(),
-            provider: None,
-            validation_endpoint: None,
-            scopes: vec![],
-            user_id: "test".to_string(),
-            secrets,
-            sse_manager: None,
-            gateway_token: None,
-            token_exchange_extra_params: std::collections::HashMap::new(),
-            client_id_secret_name: None,
-            created_at,
-        };
-
-        ext_mgr
-            .pending_oauth_flows()
-            .write()
-            .await
-            .insert("test_nonce".to_string(), flow);
-
-        let state = test_gateway_state(Some(ext_mgr.clone()));
-        let app = test_oauth_router(state);
-        let versioned_state =
-            crate::cli::oauth_defaults::encode_hosted_oauth_state("test_nonce", None);
-
-        let req = axum::http::Request::builder()
-            .uri(format!(
-                "/oauth/callback?code=fake_code&state={}",
-                urlencoding::encode(&versioned_state)
-            ))
-            .body(Body::empty())
-            .expect("request");
-
-        let resp = ServiceExt::<axum::http::Request<Body>>::oneshot(app, req)
-            .await
-            .expect("response");
-        assert_eq!(resp.status(), StatusCode::OK);
-
-        let body = axum::body::to_bytes(resp.into_body(), 1024 * 64)
-            .await
-            .expect("body");
-        let html = String::from_utf8_lossy(&body);
-        assert!(html.contains("Authorization Failed"));
-        assert!(
-            ext_mgr
-                .pending_oauth_flows()
-                .read()
-                .await
-                .get("test_nonce")
-                .is_none()
-        );
-    }
-
-    #[allow(clippy::await_holding_lock)]
-    #[tokio::test]
-    async fn test_oauth_callback_happy_path_with_gateway_token_fallback() {
-        use axum::body::Body;
-        use tower::ServiceExt;
-
-        let proxy = MockOauthProxyServer::start().await;
-        // Keep the process-wide env locked for the full callback so the handler
-        // sees a stable proxy URL/token configuration throughout the test.
-        let _env_guard = crate::config::helpers::lock_env();
-        let _exchange_url_guard =
-            set_env_var("IRONCLAW_OAUTH_EXCHANGE_URL", Some(&proxy.base_url()));
-        let _proxy_auth_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", None);
-        let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-test-token"));
-
-        let secrets = test_secrets_store();
-        let (ext_mgr, _wasm_tools_dir, _wasm_channels_dir) = test_ext_mgr(Arc::clone(&secrets));
-        let sse_mgr = Arc::new(SseManager::new());
-        let mut receiver = sse_mgr.sender().subscribe();
-        let flow = fresh_pending_oauth_flow(
-            Arc::clone(&secrets),
-            Some(Arc::clone(&sse_mgr)),
-            crate::cli::oauth_defaults::oauth_proxy_auth_token(),
-        );
-
-        ext_mgr
-            .pending_oauth_flows()
-            .write()
-            .await
-            .insert("test_nonce".to_string(), flow);
-
-        let state = test_gateway_state(Some(ext_mgr.clone()));
-        let app = test_oauth_router(state);
-        let versioned_state =
-            crate::cli::oauth_defaults::encode_hosted_oauth_state("test_nonce", Some("myinstance"));
-
-        let req = axum::http::Request::builder()
-            .uri(format!(
-                "/oauth/callback?code=fake_code&state={}",
-                urlencoding::encode(&versioned_state)
-            ))
-            .body(Body::empty())
-            .expect("request");
-
-        let resp = ServiceExt::<axum::http::Request<Body>>::oneshot(app, req)
-            .await
-            .expect("response");
-        assert_eq!(resp.status(), StatusCode::OK);
-
-        let body = axum::body::to_bytes(resp.into_body(), 1024 * 64)
-            .await
-            .expect("body");
-        let html = String::from_utf8_lossy(&body);
-        assert!(html.contains("Test Tool Connected"));
-
-        let requests = proxy.requests().await;
-        assert_eq!(requests.len(), 1);
-        assert_eq!(
-            requests[0].authorization.as_deref(),
-            Some("Bearer gateway-test-token")
-        );
-        assert_eq!(
-            requests[0].form.get("code").map(String::as_str),
-            Some("fake_code")
-        );
-        assert_eq!(
-            requests[0].form.get("code_verifier").map(String::as_str),
-            Some("test-code-verifier")
-        );
-
-        let access_token = secrets
-            .get_decrypted("test", "test_token")
-            .await
-            .expect("access token stored");
-        assert_eq!(access_token.expose(), "proxy-access-token");
-
-        let refresh_token = secrets
-            .get_decrypted("test", "test_token_refresh_token")
-            .await
-            .expect("refresh token stored");
-        assert_eq!(refresh_token.expose(), "proxy-refresh-token");
-
-        match receiver.recv().await.expect("auth_completed event").event {
-            crate::channels::web::types::AppEvent::AuthCompleted {
-                extension_name,
-                success,
-                ..
-            } => {
-                assert_eq!(extension_name, "test_tool");
-                assert!(success, "OAuth callback should broadcast success");
-            }
-            event => panic!("expected AuthCompleted event, got {event:?}"),
-        }
-
-        proxy.shutdown().await;
-    }
-
-    #[allow(clippy::await_holding_lock)]
-    #[tokio::test]
-    async fn test_oauth_callback_happy_path_with_dedicated_proxy_auth_token() {
-        use axum::body::Body;
-        use tower::ServiceExt;
-
-        let proxy = MockOauthProxyServer::start().await;
-        // Keep the process-wide env locked for the full callback so the handler
-        // sees a stable proxy URL/token configuration throughout the test.
-        let _env_guard = crate::config::helpers::lock_env();
-        let _exchange_url_guard =
-            set_env_var("IRONCLAW_OAUTH_EXCHANGE_URL", Some(&proxy.base_url()));
-        let _proxy_auth_guard = set_env_var(
-            "IRONCLAW_OAUTH_PROXY_AUTH_TOKEN",
-            Some("shared-oauth-proxy-secret"),
-        );
-        let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", None);
-
-        let secrets = test_secrets_store();
-        let (ext_mgr, _wasm_tools_dir, _wasm_channels_dir) = test_ext_mgr(Arc::clone(&secrets));
-        let sse_mgr = Arc::new(SseManager::new());
-        let mut receiver = sse_mgr.sender().subscribe();
-        let flow = fresh_pending_oauth_flow(
-            Arc::clone(&secrets),
-            Some(Arc::clone(&sse_mgr)),
-            crate::cli::oauth_defaults::oauth_proxy_auth_token(),
-        );
-
-        ext_mgr
-            .pending_oauth_flows()
-            .write()
-            .await
-            .insert("test_nonce".to_string(), flow);
-
-        let state = test_gateway_state(Some(ext_mgr.clone()));
-        let app = test_oauth_router(state);
-        let versioned_state =
-            crate::cli::oauth_defaults::encode_hosted_oauth_state("test_nonce", None);
-
-        let req = axum::http::Request::builder()
-            .uri(format!(
-                "/oauth/callback?code=fake_code&state={}",
-                urlencoding::encode(&versioned_state)
-            ))
-            .body(Body::empty())
-            .expect("request");
-
-        let resp = ServiceExt::<axum::http::Request<Body>>::oneshot(app, req)
-            .await
-            .expect("response");
-        assert_eq!(resp.status(), StatusCode::OK);
-
-        let body = axum::body::to_bytes(resp.into_body(), 1024 * 64)
-            .await
-            .expect("body");
-        let html = String::from_utf8_lossy(&body);
-        assert!(html.contains("Test Tool Connected"));
-
-        let requests = proxy.requests().await;
-        assert_eq!(requests.len(), 1);
-        assert_eq!(
-            requests[0].authorization.as_deref(),
-            Some("Bearer shared-oauth-proxy-secret")
-        );
-        assert_eq!(
-            requests[0].form.get("code").map(String::as_str),
-            Some("fake_code")
-        );
-        assert_eq!(
-            requests[0].form.get("code_verifier").map(String::as_str),
-            Some("test-code-verifier")
-        );
-
-        let access_token = secrets
-            .get_decrypted("test", "test_token")
-            .await
-            .expect("access token stored");
-        assert_eq!(access_token.expose(), "proxy-access-token");
-
-        let refresh_token = secrets
-            .get_decrypted("test", "test_token_refresh_token")
-            .await
-            .expect("refresh token stored");
-        assert_eq!(refresh_token.expose(), "proxy-refresh-token");
-
-        match receiver.recv().await.expect("auth_completed event").event {
-            crate::channels::web::types::AppEvent::AuthCompleted {
-                extension_name,
-                success,
-                ..
-            } => {
-                assert_eq!(extension_name, "test_tool");
-                assert!(success, "OAuth callback should broadcast success");
-            }
-            event => panic!("expected AuthCompleted event, got {event:?}"),
-        }
-
-        proxy.shutdown().await;
-    }
-
     // --- Slack relay OAuth CSRF tests ---
 
     fn test_relay_oauth_router(state: Arc<GatewayState>) -> Router {

src/cli/oauth_defaults.rs

@@ -473,8 +473,7 @@ pub struct PendingOAuthFlow {
     pub secrets: Arc<dyn SecretsStore + Send + Sync>,
     /// SSE broadcast manager for notifying the web UI.
     pub sse_manager: Option<Arc<crate::channels::web::sse::SseManager>>,
-    /// OAuth proxy auth token for authenticating with the hosted token exchange proxy.
+    /// Gateway auth token for authenticating with the platform token exchange proxy.
-    /// Kept as `gateway_token` for public API compatibility.
     pub gateway_token: Option<String>,
     /// Additional form params for the token exchange request.
     /// Used for provider-specific requirements such as RFC 8707 `resource`.
@@ -497,12 +496,6 @@ impl std::fmt::Debug for PendingOAuthFlow {
     }
 }
 
-impl PendingOAuthFlow {
-    pub fn oauth_proxy_auth_token(&self) -> Option<&str> {
-        self.gateway_token.as_deref()
-    }
-}
-
 /// Thread-safe registry of pending OAuth flows, keyed by CSRF `state` parameter.
 pub type PendingOAuthRegistry = Arc<RwLock<HashMap<String, PendingOAuthFlow>>>;
 
@@ -536,22 +529,6 @@ pub fn exchange_proxy_url() -> Option<String> {
         .filter(|url| !url.is_empty())
 }
 
-/// Returns the configured OAuth proxy auth token, if any.
-///
-/// New hosted infra can inject a dedicated shared proxy secret via
-/// `IRONCLAW_OAUTH_PROXY_AUTH_TOKEN`. Existing hosted instances continue to
-/// work by falling back to `GATEWAY_AUTH_TOKEN`.
-pub fn oauth_proxy_auth_token() -> Option<String> {
-    fn normalized_env_value(key: &str) -> Option<String> {
-        crate::config::helpers::env_or_override(key)
-            .map(|value| value.trim().to_string())
-            .filter(|value| !value.is_empty())
-    }
-
-    normalized_env_value("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN")
-        .or_else(|| normalized_env_value("GATEWAY_AUTH_TOKEN"))
-}
-
 /// Maximum age for pending OAuth flows (5 minutes, matching TCP listener timeout).
 pub const OAUTH_FLOW_EXPIRY: Duration = Duration::from_secs(300);
 
@@ -697,8 +674,6 @@ pub fn strip_instance_prefix(state: &str) -> &str {
 
 pub struct ProxyTokenExchangeRequest<'a> {
     pub proxy_url: &'a str,
-    /// OAuth proxy auth token.
-    /// Kept as `gateway_token` for public API compatibility.
     pub gateway_token: &'a str,
     pub token_url: &'a str,
     pub client_id: &'a str,
@@ -712,8 +687,6 @@ pub struct ProxyTokenExchangeRequest<'a> {
 
 pub struct ProxyRefreshTokenRequest<'a> {
     pub proxy_url: &'a str,
-    /// OAuth proxy auth token.
-    /// Kept as `gateway_token` for public API compatibility.
     pub gateway_token: &'a str,
     pub token_url: &'a str,
     pub client_id: &'a str,
@@ -756,7 +729,7 @@ fn oauth_token_response_from_json(
 
 /// Exchange an OAuth authorization code via the platform's token exchange proxy.
 ///
-/// Authenticated via an OAuth proxy auth token (Bearer header). The caller may
+/// Authenticated via the gateway auth token (Bearer header). The caller may
 /// either rely on proxy-side secret lookup or forward a `client_secret` when
 /// the provider requires it.
 ///
@@ -768,7 +741,7 @@ pub async fn exchange_via_proxy(
 ) -> Result<OAuthTokenResponse, OAuthCallbackError> {
     if request.gateway_token.is_empty() {
         return Err(OAuthCallbackError::Io(
-            "OAuth proxy auth token is required for proxy token exchange".to_string(),
+            "Gateway auth token is required for proxy token exchange".to_string(),
         ));
     }
     let exchange_url = format!("{}/oauth/exchange", request.proxy_url.trim_end_matches('/'));
@@ -823,7 +796,7 @@ pub async fn exchange_via_proxy(
 
 /// Refresh an OAuth access token via the platform's token refresh proxy.
 ///
-/// Authenticated via an OAuth proxy auth token (Bearer header). The caller may
+/// Authenticated via the gateway auth token (Bearer header). The caller may
 /// either rely on proxy-side secret lookup or forward a `client_secret` when
 /// the provider requires it.
 pub async fn refresh_token_via_proxy(
@@ -831,7 +804,7 @@ pub async fn refresh_token_via_proxy(
 ) -> Result<OAuthTokenResponse, OAuthCallbackError> {
     if request.gateway_token.is_empty() {
         return Err(OAuthCallbackError::Io(
-            "OAuth proxy auth token is required for proxy token refresh".to_string(),
+            "Gateway auth token is required for proxy token refresh".to_string(),
         ));
     }
 
@@ -1037,37 +1010,6 @@ mod tests {
         }
     }
 
-    struct EnvVarGuard {
-        key: &'static str,
-        original: Option<String>,
-    }
-
-    impl Drop for EnvVarGuard {
-        fn drop(&mut self) {
-            // SAFETY: Under ENV_MUTEX, no concurrent env access.
-            unsafe {
-                if let Some(ref value) = self.original {
-                    std::env::set_var(self.key, value);
-                } else {
-                    std::env::remove_var(self.key);
-                }
-            }
-        }
-    }
-
-    fn set_env_var(key: &'static str, value: Option<&str>) -> EnvVarGuard {
-        let original = std::env::var(key).ok();
-        // SAFETY: Under ENV_MUTEX, no concurrent env access.
-        unsafe {
-            if let Some(value) = value {
-                std::env::set_var(key, value);
-            } else {
-                std::env::remove_var(key);
-            }
-        }
-        EnvVarGuard { key, original }
-    }
-
     #[test]
     fn test_hosted_proxy_client_secret_suppresses_builtin_secret() {
         let builtin = builtin_credentials("google_oauth_token").expect("google builtin creds");
@@ -1088,79 +1030,6 @@ mod tests {
         assert_eq!(result, client_secret);
     }
 
-    #[tokio::test]
-    async fn test_exchange_via_proxy_sends_auth_and_form() {
-        let server = MockProxyServer::start().await;
-        let mut extra_token_params = HashMap::new();
-        extra_token_params.insert("resource".to_string(), "https://mcp.notion.com".to_string());
-
-        let response = super::exchange_via_proxy(super::ProxyTokenExchangeRequest {
-            proxy_url: &server.base_url(),
-            gateway_token: "shared-oauth-proxy-secret",
-            code: "auth-code-123",
-            redirect_uri: "https://oauth.example.com/oauth/callback",
-            token_url: "https://oauth2.googleapis.com/token",
-            client_id: TEST_OAUTH_CLIENT_ID,
-            client_secret: Some(TEST_OAUTH_CLIENT_SECRET),
-            access_token_field: "access_token",
-            code_verifier: Some("code-verifier-123"),
-            extra_token_params: &extra_token_params,
-        })
-        .await
-        .expect("proxy exchange succeeds");
-
-        assert_eq!(response.access_token, "proxy-access-token");
-        assert_eq!(
-            response.refresh_token.as_deref(),
-            Some("proxy-refresh-token")
-        );
-        assert_eq!(response.expires_in, Some(7200));
-
-        let requests = server.requests().await;
-        assert_eq!(requests.len(), 1);
-        assert_eq!(
-            requests[0].authorization.as_deref(),
-            Some("Bearer shared-oauth-proxy-secret")
-        );
-        assert_eq!(
-            requests[0].form.get("code").map(String::as_str),
-            Some("auth-code-123")
-        );
-        assert_eq!(
-            requests[0].form.get("redirect_uri").map(String::as_str),
-            Some("https://oauth.example.com/oauth/callback")
-        );
-        assert_eq!(
-            requests[0].form.get("token_url").map(String::as_str),
-            Some("https://oauth2.googleapis.com/token")
-        );
-        assert_eq!(
-            requests[0].form.get("client_id").map(String::as_str),
-            Some(TEST_OAUTH_CLIENT_ID)
-        );
-        assert_eq!(
-            requests[0].form.get("client_secret").map(String::as_str),
-            Some(TEST_OAUTH_CLIENT_SECRET)
-        );
-        assert_eq!(
-            requests[0]
-                .form
-                .get("access_token_field")
-                .map(String::as_str),
-            Some("access_token")
-        );
-        assert_eq!(
-            requests[0].form.get("code_verifier").map(String::as_str),
-            Some("code-verifier-123")
-        );
-        assert_eq!(
-            requests[0].form.get("resource").map(String::as_str),
-            Some("https://mcp.notion.com")
-        );
-
-        server.shutdown().await;
-    }
-
     #[tokio::test]
     async fn test_refresh_token_via_proxy_sends_auth_and_form() {
         let server = MockProxyServer::start().await;
@@ -1666,54 +1535,6 @@ mod tests {
         }
     }
 
-    #[test]
-    fn test_oauth_proxy_auth_token_prefers_dedicated_env() {
-        let _guard = lock_env();
-        let _proxy_guard = set_env_var(
-            "IRONCLAW_OAUTH_PROXY_AUTH_TOKEN",
-            Some("shared-proxy-secret"),
-        );
-        let _gateway_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-token"));
-
-        assert_eq!(
-            crate::cli::oauth_defaults::oauth_proxy_auth_token().as_deref(),
-            Some("shared-proxy-secret")
-        );
-    }
-
-    #[test]
-    fn test_oauth_proxy_auth_token_falls_back_to_gateway_token() {
-        let _guard = lock_env();
-        let _proxy_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", None);
-        let _gateway_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-token"));
-
-        assert_eq!(
-            crate::cli::oauth_defaults::oauth_proxy_auth_token().as_deref(),
-            Some("gateway-token")
-        );
-    }
-
-    #[test]
-    fn test_oauth_proxy_auth_token_whitespace_dedicated_env_falls_back_to_gateway_token() {
-        let _guard = lock_env();
-        let _proxy_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", Some("   "));
-        let _gateway_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-token"));
-
-        assert_eq!(
-            crate::cli::oauth_defaults::oauth_proxy_auth_token().as_deref(),
-            Some("gateway-token")
-        );
-    }
-
-    #[test]
-    fn test_oauth_proxy_auth_token_returns_none_when_unset() {
-        let _guard = lock_env();
-        let _proxy_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", None);
-        let _gateway_guard = set_env_var("GATEWAY_AUTH_TOKEN", None);
-
-        assert_eq!(crate::cli::oauth_defaults::oauth_proxy_auth_token(), None);
-    }
-
     #[test]
     fn test_strip_instance_prefix_with_colon() {
         use crate::cli::oauth_defaults::strip_instance_prefix;

src/context/state.rs

@@ -192,9 +192,6 @@ 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

@@ -403,10 +403,9 @@ pub struct ExtensionManager {
     /// when running in gateway mode, consumed by the web gateway's
     /// `/oauth/callback` handler.
     pending_oauth_flows: crate::cli::oauth_defaults::PendingOAuthRegistry,
-    /// OAuth proxy auth token for authenticating with the hosted token exchange proxy.
+    /// Gateway auth token for authenticating with the platform token exchange proxy.
-    /// Resolved once at construction from `IRONCLAW_OAUTH_PROXY_AUTH_TOKEN`,
+    /// Read once at construction from `GATEWAY_AUTH_TOKEN` env var.
-    /// then `GATEWAY_AUTH_TOKEN` as a backward-compatible fallback.
+    gateway_token: Option<String>,
-    oauth_proxy_auth_token: Option<String>,
     /// Relay config captured at startup. Used by `auth_channel_relay` and
     /// `activate_channel_relay` instead of re-reading env vars.
     relay_config: Option<crate::config::RelayConfig>,
@@ -536,7 +535,7 @@ impl ExtensionManager {
             activation_errors: RwLock::new(HashMap::new()),
             sse_manager: RwLock::new(None),
             pending_oauth_flows: crate::cli::oauth_defaults::new_pending_oauth_registry(),
-            oauth_proxy_auth_token: crate::cli::oauth_defaults::oauth_proxy_auth_token(),
+            gateway_token: std::env::var("GATEWAY_AUTH_TOKEN").ok(),
             relay_config: crate::config::RelayConfig::from_env(),
             relay_event_tx: Arc::new(tokio::sync::Mutex::new(None)),
             relay_signing_secret_cache: Arc::new(std::sync::Mutex::new(None)),
@@ -660,66 +659,6 @@ 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,
@@ -953,46 +892,6 @@ 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
@@ -1519,7 +1418,7 @@ impl ExtensionManager {
             let errors = self.activation_errors.read().await;
             for name in installed.iter() {
                 let active = active_names.contains(name);
-                let authenticated = self.has_stored_team_id(name, user_id).await;
+                let authenticated = self.is_relay_channel(name, user_id).await;
                 let activation_error = errors.get(name).cloned();
                 let registry_entry = self
                     .registry
@@ -2789,7 +2688,7 @@ impl ExtensionManager {
                 user_id: user_id.to_string(),
                 secrets: Arc::clone(&self.secrets),
                 sse_manager: self.sse_manager.read().await.clone(),
-                gateway_token: self.oauth_proxy_auth_token.clone(),
+                gateway_token: self.gateway_token.clone(),
                 token_exchange_extra_params,
                 client_id_secret_name: if server.oauth.is_none() {
                     Some(server.client_id_secret_name())
@@ -3306,7 +3205,7 @@ impl ExtensionManager {
                 user_id: user_id.to_string(),
                 secrets: Arc::clone(&self.secrets),
                 sse_manager: self.sse_manager.read().await.clone(),
-                gateway_token: self.oauth_proxy_auth_token.clone(),
+                gateway_token: self.gateway_token.clone(),
                 token_exchange_extra_params: std::collections::HashMap::new(),
                 client_id_secret_name: None,
                 created_at: std::time::Instant::now(),
@@ -4292,69 +4191,20 @@ impl ExtensionManager {
         name: &str,
         user_id: &str,
     ) -> Result<AuthResult, ExtensionError> {
-        tracing::debug!(
+        // Check if already authenticated (team_id setting exists)
-            extension = %name,
+        if self.is_relay_channel(name, user_id).await {
-            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().map_err(|e| {
+        let relay_config = self.relay_config()?;
-            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(
-            effective_url.clone(),
+            relay_config.url.clone(),
             relay_config.api_key.clone(),
             relay_config.request_timeout_secs,
         )
-        .map_err(|e| {
+        .map_err(|e| ExtensionError::Config(e.to_string()))?;
-            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
@@ -4366,44 +4216,18 @@ impl ExtensionManager {
         self.secrets
             .create(user_id, CreateSecretParams::new(&state_key, &state_nonce))
             .await
-            .map_err(|e| {
+            .map_err(|e| ExtensionError::AuthFailed(format!("Failed to store OAuth state: {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(auth_url) => Ok(AuthResult::awaiting_authorization(
-                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) => Err(ExtensionError::AuthFailed(e.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()))
-            }
         }
     }
 
@@ -4413,112 +4237,40 @@ 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 {
-            match store.get_setting(user_id, &team_id_key).await {
+            store
-                Ok(Some(v)) => {
+                .get_setting(user_id, &team_id_key)
-                    let id = v.as_str().map(|s| s.to_string()).unwrap_or_default();
+                .await
-                    tracing::debug!(
+                .ok()
-                        extension = %name,
+                .flatten()
-                        team_id_empty = id.is_empty(),
+                .and_then(|v| v.as_str().map(|s| s.to_string()))
-                        "activate_channel_relay: loaded team_id from store"
+                .unwrap_or_default()
-                    );
-                    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().map_err(|e| {
+        let relay_config = self.relay_config()?;
-            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(
-            effective_url.clone(),
+            relay_config.url.clone(),
             relay_config.api_key.clone(),
             relay_config.request_timeout_secs,
         )
-        .map_err(|e| {
+        .map_err(|e| ExtensionError::ActivationFailed(e.to_string()))?;
-            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}"))
         })?;
 
@@ -4537,29 +4289,16 @@ 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| {
+        channel_mgr
-            tracing::warn!(
+            .hot_add(Box::new(channel))
-                extension = %name,
+            .await
-                error = %e,
+            .map_err(|e| ExtensionError::ActivationFailed(e.to_string()))?;
-                "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
@@ -4577,12 +4316,6 @@ 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,
@@ -4862,41 +4595,6 @@ 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(),
@@ -5299,17 +4997,7 @@ impl ExtensionManager {
                 names.insert(server.token_secret_name());
                 (names, Vec::new())
             }
-            ExtensionKind::ChannelRelay => {
+            ExtensionKind::ChannelRelay => (std::collections::HashSet::new(), Vec::new()),
-                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> =
@@ -5400,28 +5088,13 @@ 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) = field_def {
+            if let Some(field_def) = setup_field_defs.get(field_name) {
                 if field_def.restart_required {
                     restart_required = true;
                 }
@@ -7385,39 +7058,6 @@ 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

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

src/llm/reasoning.rs

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

src/tools/builtin/extension_tools.rs

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

src/tools/builtin/message.rs

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

src/tools/builtin/routine.rs

@@ -650,23 +650,6 @@ 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)
 }
@@ -1110,7 +1093,6 @@ 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);
@@ -1292,7 +1274,6 @@ 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
@@ -1430,24 +1411,11 @@ impl Tool for RoutineDeleteTool {
     ) -> Result<ToolOutput, ToolError> {
         let start = std::time::Instant::now();
 
-        let name = if let Some(name) = params.get("name").and_then(|v| v.as_str()) {
+        let name = require_str(&params, "name")?;
-            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)))?;
@@ -1462,7 +1430,7 @@ 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

@@ -117,11 +117,6 @@ 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(),
@@ -219,14 +214,7 @@ impl McpClient {
         }
     }
 
-    /// Attach a session manager to the **client** only.
+    /// Attach a session manager for Streamable HTTP session tracking.
-    ///
-    /// **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
@@ -247,12 +235,6 @@ 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

@@ -7,7 +7,6 @@ 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.
@@ -79,37 +78,33 @@ 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() {
-                    return Ok(McpClient::new_authenticated(
+                    Ok(McpClient::new_authenticated(
                         server,
                         Arc::clone(session_manager),
                         Arc::clone(secrets),
                         user_id,
-                    ));
-                }
-            }
-
-            // 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),
                     ))
+                } 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)))
+            }
         }
     }
 }
@@ -139,84 +134,4 @@ 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

@@ -494,34 +494,6 @@ 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;

src/tools/wasm/loader.rs

@@ -446,14 +446,16 @@ fn resolve_oauth_refresh_config(cap_file: &CapabilitiesFile) -> Option<OAuthRefr
         builtin.as_ref(),
         exchange_proxy_url.is_some(),
     );
-    let oauth_proxy_auth_token = crate::cli::oauth_defaults::oauth_proxy_auth_token();
+    let gateway_token = crate::config::helpers::env_or_override("GATEWAY_AUTH_TOKEN")
+        .map(|token| token.trim().to_string())
+        .filter(|token| !token.is_empty());
 
     Some(OAuthRefreshConfig {
         token_url: oauth.token_url.clone(),
         client_id,
         client_secret,
         exchange_proxy_url,
-        gateway_token: oauth_proxy_auth_token,
+        gateway_token,
         secret_name: auth.secret_name.clone(),
         provider: auth.provider.clone(),
     })
@@ -889,11 +891,6 @@ mod tests {
             AuthCapabilitySchema, CapabilitiesFile, OAuthConfigSchema,
         };
 
-        let _guard = lock_env();
-        let _proxy_guard = set_env_var("IRONCLAW_OAUTH_EXCHANGE_URL", None);
-        let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", None);
-        let _oauth_proxy_token_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", None);
-
         let caps = CapabilitiesFile {
             auth: Some(AuthCapabilitySchema {
                 secret_name: "google_oauth_token".to_string(),
@@ -985,7 +982,6 @@ mod tests {
         let _guard = lock_env();
         let _proxy_guard = set_env_var("IRONCLAW_OAUTH_EXCHANGE_URL", None);
         let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", None);
-        let _oauth_proxy_token_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", None);
 
         // google_oauth_token should fall back to built-in credentials
         let caps = CapabilitiesFile {
@@ -1025,7 +1021,6 @@ mod tests {
             Some("https://compose-api.example.com"),
         );
         let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-test-token"));
-        let _oauth_proxy_token_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", None);
         let _client_id_guard =
             set_env_var("GOOGLE_OAUTH_CLIENT_ID", Some("hosted-google-client-id"));
 
@@ -1066,7 +1061,6 @@ mod tests {
             Some("https://compose-api.example.com"),
         );
         let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-test-token"));
-        let _oauth_proxy_token_guard = set_env_var("IRONCLAW_OAUTH_PROXY_AUTH_TOKEN", None);
         let _client_id_guard =
             set_env_var("GOOGLE_OAUTH_CLIENT_ID", Some("hosted-google-client-id"));
         let _client_secret_guard =
@@ -1101,47 +1095,6 @@ mod tests {
         assert_eq!(config.gateway_token.as_deref(), Some("gateway-test-token"));
     }
 
-    #[test]
-    fn test_resolve_oauth_refresh_config_hosted_proxy_prefers_dedicated_proxy_auth_token() {
-        use crate::tools::wasm::capabilities_schema::{
-            AuthCapabilitySchema, CapabilitiesFile, OAuthConfigSchema,
-        };
-
-        let _guard = lock_env();
-        let _proxy_guard = set_env_var(
-            "IRONCLAW_OAUTH_EXCHANGE_URL",
-            Some("https://compose-api.example.com"),
-        );
-        let _gateway_token_guard = set_env_var("GATEWAY_AUTH_TOKEN", Some("gateway-test-token"));
-        let _oauth_proxy_token_guard = set_env_var(
-            "IRONCLAW_OAUTH_PROXY_AUTH_TOKEN",
-            Some("shared-oauth-proxy-secret"),
-        );
-        let _client_id_guard =
-            set_env_var("GOOGLE_OAUTH_CLIENT_ID", Some("hosted-google-client-id"));
-
-        let caps = CapabilitiesFile {
-            auth: Some(AuthCapabilitySchema {
-                secret_name: "google_oauth_token".to_string(),
-                provider: Some("google".to_string()),
-                oauth: Some(OAuthConfigSchema {
-                    authorization_url: "https://accounts.google.com/o/oauth2/v2/auth".to_string(),
-                    token_url: "https://oauth2.googleapis.com/token".to_string(),
-                    client_id_env: Some("GOOGLE_OAUTH_CLIENT_ID".to_string()),
-                    ..Default::default()
-                }),
-                ..Default::default()
-            }),
-            ..Default::default()
-        };
-
-        let config = super::resolve_oauth_refresh_config(&caps).expect("hosted oauth config");
-        assert_eq!(
-            config.gateway_token.as_deref(),
-            Some("shared-oauth-proxy-secret")
-        );
-    }
-
     // ---------------------------------------------------------------
     // Security regression tests
     // ---------------------------------------------------------------

src/tools/wasm/wrapper.rs

@@ -62,8 +62,7 @@ pub struct OAuthRefreshConfig {
     pub client_secret: Option<String>,
     /// Hosted OAuth proxy base URL (e.g., "http://host.docker.internal:8080").
     pub exchange_proxy_url: Option<String>,
-    /// OAuth proxy auth token for authenticating with the hosted OAuth proxy.
+    /// Gateway auth token for authenticating with the hosted OAuth proxy.
-    /// Kept as `gateway_token` for public API compatibility.
     pub gateway_token: Option<String>,
     /// Secret name of the access token (e.g., "google_oauth_token").
     /// The refresh token lives at `{secret_name}_refresh_token`.
@@ -72,12 +71,6 @@ pub struct OAuthRefreshConfig {
     pub provider: Option<String>,
 }
 
-impl OAuthRefreshConfig {
-    fn oauth_proxy_auth_token(&self) -> Option<&str> {
-        self.gateway_token.as_deref()
-    }
-}
-
 /// Pre-resolved credential for host-based injection.
 ///
 /// Built before each WASM execution by decrypting secrets from the store.
@@ -1225,9 +1218,9 @@ async fn refresh_oauth_token(
     let refresh_name = format!("{}_refresh_token", config.secret_name);
 
     if let Some(proxy_url) = config.exchange_proxy_url.as_deref() {
-        let Some(oauth_proxy_auth_token) = config.oauth_proxy_auth_token() else {
+        let Some(gateway_token) = config.gateway_token.as_deref() else {
             tracing::warn!(
-                "OAuth refresh proxy is configured, but no OAuth proxy auth token is available"
+                "OAuth refresh proxy is configured, but no gateway auth token is available"
             );
             return false;
         };
@@ -1242,7 +1235,7 @@ async fn refresh_oauth_token(
         let token_response = match oauth_defaults::refresh_token_via_proxy(
             oauth_defaults::ProxyRefreshTokenRequest {
                 proxy_url,
-                gateway_token: oauth_proxy_auth_token,
+                gateway_token,
                 token_url: &config.token_url,
                 client_id: &config.client_id,
                 client_secret: config.client_secret.as_deref(),
@@ -2711,8 +2704,7 @@ mod tests {
     }
 
     #[tokio::test]
-    async fn test_resolve_host_credentials_skips_refresh_token_lookup_without_oauth_proxy_auth_token()
+    async fn test_resolve_host_credentials_skips_refresh_token_lookup_without_gateway_token() {
-     {
         use crate::secrets::{
             CreateSecretParams, CredentialLocation, CredentialMapping, SecretsStore,
         };

tests/e2e_builtin_tool_coverage.rs

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

tests/fixtures/llm_traces/tools/routine_update_fail_delete_fallback.json

@@ -1,70 +0,0 @@
-{
-  "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

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