Format prompt guidance assertions

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

.gitignore

@@ -17,8 +17,6 @@ target/
 # Python
 __pycache__/
 *.pyc
-*.pyo
-*.pyd
 
 # Benchmark results (local runs, not committed)
 bench-results/
@@ -36,5 +34,8 @@ trace_*.json
 .claude/settings.local.json
 .worktrees/
 
-# JetBrains IDE
-.idea
+# Python cache
+__pycache__/
+*.pyc
+*.pyo
+*.pyd

channels-src/whatsapp/Cargo.lock

@@ -269,7 +269,7 @@ dependencies = [
 
 [[package]]
 name = "whatsapp-channel"
-version = "0.2.0"
+version = "0.1.0"
 dependencies = [
  "serde",
  "serde_json",

src/agent/dispatcher.rs

@@ -47,15 +47,6 @@ impl Agent {
         thread_id: Uuid,
         initial_messages: Vec<ChatMessage>,
     ) -> Result<AgenticLoopResult, Error> {
-        if let Some(ext_mgr) = self.deps.extension_manager.as_ref()
-            && let Err(e) = ext_mgr.ensure_nearai_companion_active_if_ready().await
-        {
-            tracing::debug!(
-                "Failed to auto-activate NEAR AI companion MCP before turn: {}",
-                e
-            );
-        }
-
         // Detect group chat from channel metadata (needed before loading system prompt)
         let is_group_chat = message
             .metadata

src/app.rs

@@ -449,8 +449,6 @@ impl AppBuilder {
 
         let mcp_session_manager = Arc::new(McpSessionManager::new());
         let mcp_process_manager = Arc::new(McpProcessManager::new());
-        let companion_mcp_server =
-            crate::tools::mcp::config::derive_nearai_companion_mcp_server(&self.config);
 
         // Create WASM tool runtime eagerly so extensions installed after startup
         // (e.g. via the web UI) can still be activated. The tools directory is only
@@ -528,7 +526,6 @@ impl AppBuilder {
             let mcp_sm = Arc::clone(&mcp_session_manager);
             let pm = Arc::clone(&mcp_process_manager);
             let owner_id = self.config.owner_id.clone();
-            let companion_mcp_server = companion_mcp_server.clone();
             async move {
                 let servers_result = if let Some(ref d) = db {
                     load_mcp_servers_from_db(d.as_ref(), &owner_id).await
@@ -536,16 +533,7 @@ impl AppBuilder {
                     crate::tools::mcp::config::load_mcp_servers().await
                 };
                 match servers_result {
-                    Ok(mut servers) => {
-                        if let Some(companion) = companion_mcp_server {
-                            let companion_name = companion.name.clone();
-                            if !servers.insert_if_absent(companion) {
-                                tracing::debug!(
-                                    "Skipping derived MCP companion '{}': an existing config with that name is already present",
-                                    companion_name
-                                );
-                            }
-                        }
+                    Ok(servers) => {
                         let enabled: Vec<_> = servers.enabled_servers().cloned().collect();
                         if !enabled.is_empty() {
                             tracing::debug!(
@@ -557,8 +545,6 @@ impl AppBuilder {
                         let mut join_set = tokio::task::JoinSet::new();
                         for server in enabled {
                             let mcp_sm = Arc::clone(&mcp_sm);
-                            let nearai_session = Arc::clone(&self.session);
-                            let nearai_api_key = self.config.llm.nearai.api_key.clone();
                             let secrets = secrets_store.clone();
                             let tools = Arc::clone(&tools);
                             let pm = Arc::clone(&pm);
@@ -570,8 +556,6 @@ impl AppBuilder {
                                 let client = match crate::tools::mcp::create_client_from_config(
                                     server,
                                     &mcp_sm,
-                                    Some(nearai_session),
-                                    nearai_api_key,
                                     &pm,
                                     secrets,
                                     &owner_id,
@@ -728,8 +712,6 @@ impl AppBuilder {
             let manager = Arc::new(ExtensionManager::new(
                 Arc::clone(&mcp_session_manager),
                 Arc::clone(&mcp_process_manager),
-                Some(Arc::clone(&self.session)),
-                self.config.llm.nearai.api_key.clone(),
                 ext_secrets,
                 Arc::clone(tools),
                 Some(Arc::clone(hooks)),
@@ -739,7 +721,6 @@ impl AppBuilder {
                 self.config.tunnel.public_url.clone(),
                 self.config.owner_id.clone(),
                 self.db.clone(),
-                companion_mcp_server,
                 catalog_entries.clone(),
             ));
             tools.register_extension_tools(Arc::clone(&manager));

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| {
-                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"
-        );
+            .map_err(|e| RelayError::Network(e.to_string()))?;
 
         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| {
-                tracing::warn!(
-                    relay_url = %url,
-                    error = %e,
-                    "RelayClient::proxy_provider: network request failed"
-                );
-                RelayError::Network(e.to_string())
-            })?;
+            .map_err(|e| 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| {
-                tracing::warn!(
-                    relay_url = %url,
-                    error = %e,
-                    "RelayClient::get_signing_secret: network request failed"
-                );
-                RelayError::Network(e.to_string())
-            })?;
+            .map_err(|e| 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/handlers/extensions.rs

@@ -70,7 +70,6 @@ pub async fn extensions_list_handler(
                 tools: ext.tools,
                 needs_setup: ext.needs_setup,
                 has_auth: ext.has_auth,
-                derived: ext.derived,
                 activation_status,
                 activation_error: ext.activation_error,
                 version: ext.version,

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!(
-            relay = DEFAULT_RELAY_NAME,
-            owner_id = %state.owner_id,
-            team_id_key = %team_id_key,
-            "relay OAuth callback: storing team_id in settings"
-        );
-        store
+        let _ = store
             .set_setting(&state.owner_id, &team_id_key, &serde_json::json!(team_id))
-            .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}")
-            })?;
+            .await;
 
         // 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
@@ -2092,7 +2072,6 @@ async fn extensions_list_handler(
                 tools: ext.tools,
                 needs_setup: ext.needs_setup,
                 has_auth: ext.has_auth,
-                derived: ext.derived,
                 activation_status,
                 activation_error: ext.activation_error,
                 version: ext.version,
@@ -2202,11 +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(),
@@ -2214,10 +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).
@@ -2236,13 +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())));
             }
@@ -2250,21 +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) => {
-                            tracing::warn!(
-                                extension = %name,
-                                error = %e,
-                                "extensions_activate_handler: retry after auth still failed"
-                            );
-                            Ok(Json(ActionResponse::fail(e.to_string())))
-                        }
+                        Err(e) => Ok(Json(ActionResponse::fail(e.to_string()))),
                     }
                 }
                 Ok(auth_result) => {
@@ -2949,7 +2901,6 @@ mod tests {
             tools: Vec::new(),
             needs_setup: true,
             has_auth: false,
-            derived: false,
             installed: true,
             activation_error: None,
             version: None,
@@ -2987,7 +2938,6 @@ mod tests {
             tools: Vec::new(),
             needs_setup: true,
             has_auth: false,
-            derived: false,
             installed: true,
             activation_error: None,
             version: None,
@@ -3060,160 +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;
@@ -3871,284 +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 {
@@ -4180,8 +3698,6 @@ mod tests {
         let ext_mgr = Arc::new(ExtensionManager::new(
             mcp_sm,
             mcp_pm,
-            None,
-            None,
             secrets,
             tool_registry,
             None,
@@ -4191,7 +3707,6 @@ mod tests {
             None,
             "test".to_string(),
             None,
-            None,
             vec![],
         ));
         (ext_mgr, wasm_tools_dir, wasm_channels_dir)

src/channels/web/static/app.js

@@ -1160,7 +1160,7 @@ function addToolCard(name) {
 
   const toolName = document.createElement('span');
   toolName.className = 'activity-tool-name';
-  toolName.textContent = humanizeToolName(name);
+  toolName.textContent = name;
 
   const duration = document.createElement('span');
   duration.className = 'activity-tool-duration';
@@ -1344,7 +1344,7 @@ function finalizeActivityGroup() {
 
 function humanizeToolName(rawName) {
   if (!rawName) return '';
-  return stripDerivedCompanionToolPrefix(String(rawName))
+  return String(rawName)
     .replace(/[_-]+/g, ' ')
     .replace(/([a-z0-9])([A-Z])/g, '$1 $2')
     .replace(/^tool([a-zA-Z])/, 'tool $1')
@@ -1352,12 +1352,6 @@ function humanizeToolName(rawName) {
     .trim();
 }
 
-function stripDerivedCompanionToolPrefix(rawName) {
-  if (!rawName) return '';
-  const prefix = '_nearai_companion_mcp_';
-  return rawName.startsWith(prefix) ? rawName.slice(prefix.length) : rawName;
-}
-
 function shouldShowChannelConnectedMessage(extensionName, success) {
   if (!success || !extensionName) return false;
   return String(extensionName).toLowerCase().includes('telegram');
@@ -1877,7 +1871,7 @@ function createToolCallsSummaryElement(toolCalls) {
     const icon = tc.has_error ? '\u2717' : '\u2713';
     const nameSpan = document.createElement('span');
     nameSpan.className = 'tool-call-name';
-    nameSpan.textContent = icon + ' ' + humanizeToolName(tc.name);
+    nameSpan.textContent = icon + ' ' + tc.name;
     item.appendChild(nameSpan);
 
     if (tc.result_preview) {
@@ -2912,12 +2906,7 @@ function renderExtensionCard(ext) {
   if (ext.tools && ext.tools.length > 0) {
     const tools = document.createElement('div');
     tools.className = 'ext-tools';
-    const toolNames = ext.tools.map((toolName) => (
-      ext.derived && ext.kind === 'mcp_server'
-        ? stripDerivedCompanionToolPrefix(toolName)
-        : toolName
-    ));
-    tools.textContent = 'Tools: ' + toolNames.join(', ');
+    tools.textContent = 'Tools: ' + ext.tools.join(', ');
     card.appendChild(tools);
   }
 
@@ -2978,7 +2967,7 @@ function renderExtensionCard(ext) {
     // Skip when has_auth is true but needs_setup is false and not yet authenticated —
     // this means OAuth credentials resolve automatically (builtin/env) and the user
     // just needs to complete the OAuth flow, not fill in a config form.
-    if (!ext.derived && (ext.needs_setup || (ext.has_auth && ext.authenticated))) {
+    if (ext.needs_setup || (ext.has_auth && ext.authenticated)) {
       const configBtn = document.createElement('button');
       configBtn.className = 'btn-ext configure';
       configBtn.textContent = ext.authenticated ? I18n.t('ext.reconfigure') : I18n.t('ext.configure');
@@ -2987,13 +2976,11 @@ function renderExtensionCard(ext) {
     }
   }
 
-  if (!ext.derived) {
-    const removeBtn = document.createElement('button');
-    removeBtn.className = 'btn-ext remove';
-    removeBtn.textContent = I18n.t('ext.remove');
-    removeBtn.addEventListener('click', () => removeExtension(ext.name));
-    actions.appendChild(removeBtn);
-  }
+  const removeBtn = document.createElement('button');
+  removeBtn.className = 'btn-ext remove';
+  removeBtn.textContent = I18n.t('ext.remove');
+  removeBtn.addEventListener('click', () => removeExtension(ext.name));
+  actions.appendChild(removeBtn);
 
   card.appendChild(actions);
 

src/channels/web/types.rs

@@ -344,9 +344,6 @@ pub struct ExtensionInfo {
     /// Whether this extension has an auth configuration (OAuth or manual token).
     #[serde(default)]
     pub has_auth: bool,
-    /// Whether this extension is derived from runtime/provider state.
-    #[serde(default)]
-    pub derived: bool,
     /// WASM channel activation status.
     #[serde(skip_serializing_if = "Option::is_none")]
     pub activation_status: Option<ExtensionActivationStatus>,

src/cli/mcp.rs

@@ -8,7 +8,7 @@ use std::sync::Arc;
 
 use clap::{Args, Subcommand};
 
-use crate::config::{Config, LlmConfig};
+use crate::config::Config;
 use crate::db::Database;
 use crate::secrets::SecretsStore;
 use crate::tools::mcp::{
@@ -173,13 +173,6 @@ async fn add_server(args: McpAddArgs) -> anyhow::Result<()> {
         description,
     } = args;
 
-    if config::is_nearai_companion_server_name(&name) {
-        anyhow::bail!(
-            "Server name '{}' is reserved for the NEAR AI companion MCP server",
-            name
-        );
-    }
-
     let transport_lower = transport.to_lowercase();
 
     let mut config = match transport_lower.as_str() {
@@ -251,7 +244,7 @@ async fn add_server(args: McpAddArgs) -> anyhow::Result<()> {
 
     // Save (DB if available, else disk)
     let db = connect_db().await;
-    let mut servers = load_persisted_servers(db.as_deref()).await?;
+    let mut servers = load_servers(db.as_deref()).await?;
     servers.upsert(config);
     save_servers(db.as_deref(), &servers).await?;
 
@@ -288,15 +281,8 @@ async fn add_server(args: McpAddArgs) -> anyhow::Result<()> {
 
 /// Remove an MCP server.
 async fn remove_server(name: String) -> anyhow::Result<()> {
-    if config::is_nearai_companion_server_name(&name) {
-        anyhow::bail!(
-            "Server '{}' is derived from the active NEAR AI provider and cannot be removed directly",
-            name
-        );
-    }
-
     let db = connect_db().await;
-    let mut servers = load_persisted_servers(db.as_deref()).await?;
+    let mut servers = load_servers(db.as_deref()).await?;
     if !servers.remove(&name) {
         anyhow::bail!("Server '{}' not found", name);
     }
@@ -312,7 +298,7 @@ async fn remove_server(name: String) -> anyhow::Result<()> {
 /// List configured MCP servers.
 async fn list_servers(verbose: bool) -> anyhow::Result<()> {
     let db = connect_db().await;
-    let servers = load_servers_with_derived(db.as_deref()).await?;
+    let servers = load_servers(db.as_deref()).await?;
 
     if servers.servers.is_empty() {
         println!();
@@ -418,23 +404,12 @@ async fn list_servers(verbose: bool) -> anyhow::Result<()> {
 async fn auth_server(name: String, user_id: String) -> anyhow::Result<()> {
     // Get server config
     let db = connect_db().await;
-    let servers = load_servers_with_derived(db.as_deref()).await?;
+    let servers = load_servers(db.as_deref()).await?;
     let server = servers
         .get(&name)
         .cloned()
         .ok_or_else(|| anyhow::anyhow!("Server '{}' not found", name))?;
 
-    if server.uses_runtime_auth_source() {
-        println!();
-        println!(
-            "  Server '{}' reuses your active NEAR AI authentication and does not support separate MCP OAuth.",
-            name
-        );
-        println!("  Configure NEAR AI auth (API key or session login) instead.");
-        println!();
-        return Ok(());
-    }
-
     // Initialize secrets store
     let secrets = get_secrets_store().await?;
 
@@ -502,7 +477,7 @@ async fn auth_server(name: String, user_id: String) -> anyhow::Result<()> {
 async fn test_server(name: String, user_id: String) -> anyhow::Result<()> {
     // Get server config
     let db = connect_db().await;
-    let servers = load_servers_with_derived(db.as_deref()).await?;
+    let servers = load_servers(db.as_deref()).await?;
     let server = servers
         .get(&name)
         .cloned()
@@ -513,66 +488,35 @@ async fn test_server(name: String, user_id: String) -> anyhow::Result<()> {
 
     // Create client
     let session_manager = Arc::new(McpSessionManager::new());
-    let (client, has_tokens) = if server.uses_runtime_auth_source() {
-        let process_manager = Arc::new(McpProcessManager::new());
-        let llm = resolve_llm_for_cli(as_settings_store(db.as_deref())).await?;
-        let nearai_session = crate::llm::create_session_manager(llm.session.clone()).await;
-        (
-            create_client_from_config(
-                server.clone(),
-                &session_manager,
-                Some(nearai_session),
-                llm.nearai.api_key.clone(),
-                &process_manager,
-                None,
-                "default",
-            )
-            .await
-            .map_err(|e| anyhow::anyhow!("{}", e))?,
-            false,
-        )
-    } else {
-        // Only initialize the secrets store for non-runtime-auth servers that
-        // can actually use persisted OAuth/DCR tokens.
-        let secrets = get_secrets_store().await?;
-        let has_tokens = is_authenticated(&server, &secrets, &user_id).await;
 
-        if has_tokens {
-            (
-                McpClient::new_authenticated(
-                    server.clone(),
-                    session_manager.clone(),
-                    secrets,
-                    user_id,
-                ),
-                true,
-            )
-        } else if server.requires_auth() {
-            println!();
-            println!(
-                "  ✗ Not authenticated. Run 'ironclaw mcp auth {}' first.",
-                name
-            );
-            println!();
-            return Ok(());
-        } else {
-            // Use the factory to dispatch on transport type (HTTP, stdio, unix)
-            let process_manager = Arc::new(McpProcessManager::new());
-            (
-                create_client_from_config(
-                    server.clone(),
-                    &session_manager,
-                    None,
-                    None,
-                    &process_manager,
-                    None,
-                    "default",
-                )
-                .await
-                .map_err(|e| anyhow::anyhow!("{}", e))?,
-                false,
-            )
-        }
+    // Always check for stored tokens (from either pre-configured OAuth or DCR)
+    let secrets = get_secrets_store().await?;
+    let has_tokens = is_authenticated(&server, &secrets, &user_id).await;
+
+    let client = if has_tokens {
+        // We have stored tokens, use authenticated client
+        McpClient::new_authenticated(server.clone(), session_manager.clone(), secrets, user_id)
+    } else if server.requires_auth() {
+        // OAuth configured but no tokens - need to authenticate
+        println!();
+        println!(
+            "  ✗ Not authenticated. Run 'ironclaw mcp auth {}' first.",
+            name
+        );
+        println!();
+        return Ok(());
+    } else {
+        // Use the factory to dispatch on transport type (HTTP, stdio, unix)
+        let process_manager = Arc::new(McpProcessManager::new());
+        create_client_from_config(
+            server.clone(),
+            &session_manager,
+            &process_manager,
+            None,
+            "default",
+        )
+        .await
+        .map_err(|e| anyhow::anyhow!("{}", e))?
     };
 
     // Test connection
@@ -637,15 +581,8 @@ async fn test_server(name: String, user_id: String) -> anyhow::Result<()> {
 
 /// Toggle server enabled/disabled state.
 async fn toggle_server(name: String, enable: bool, disable: bool) -> anyhow::Result<()> {
-    if config::is_nearai_companion_server_name(&name) {
-        anyhow::bail!(
-            "Server '{}' is derived from the active NEAR AI provider and cannot be toggled directly",
-            name
-        );
-    }
-
     let db = connect_db().await;
-    let mut servers = load_persisted_servers(db.as_deref()).await?;
+    let mut servers = load_servers(db.as_deref()).await?;
 
     let server = servers
         .get_mut(&name)
@@ -678,30 +615,13 @@ async fn connect_db() -> Option<Arc<dyn Database>> {
     crate::db::connect_from_config(&config.database).await.ok()
 }
 
-/// Load only persisted MCP servers (DB if available, else disk).
-async fn load_persisted_servers(
-    db: Option<&dyn Database>,
-) -> Result<McpServersFile, config::ConfigError> {
-    Ok(if let Some(db) = db {
-        config::load_mcp_servers_from_db(db, DEFAULT_USER_ID).await?
+/// Load MCP servers (DB if available, else disk).
+async fn load_servers(db: Option<&dyn Database>) -> Result<McpServersFile, config::ConfigError> {
+    if let Some(db) = db {
+        config::load_mcp_servers_from_db(db, DEFAULT_USER_ID).await
     } else {
-        config::load_mcp_servers().await?
-    })
-}
-
-/// Load MCP servers plus any derived runtime companions.
-async fn load_servers_with_derived(
-    db: Option<&dyn Database>,
-) -> Result<McpServersFile, config::ConfigError> {
-    let mut servers = load_persisted_servers(db).await?;
-
-    if let Ok(llm) = resolve_llm_for_cli(as_settings_store(db)).await
-        && let Some(companion) = config::derive_nearai_companion_mcp_server_from_llm(&llm)
-    {
-        servers.insert_if_absent(companion);
+        config::load_mcp_servers().await
     }
-
-    Ok(servers)
 }
 
 /// Save MCP servers (DB if available, else disk).
@@ -709,15 +629,10 @@ async fn save_servers(
     db: Option<&dyn Database>,
     servers: &McpServersFile,
 ) -> Result<(), config::ConfigError> {
-    let mut persisted = servers.clone();
-    persisted
-        .servers
-        .retain(|server| !config::is_nearai_companion_server_name(&server.name));
-
     if let Some(db) = db {
-        config::save_mcp_servers_to_db(db, DEFAULT_USER_ID, &persisted).await
+        config::save_mcp_servers_to_db(db, DEFAULT_USER_ID, servers).await
     } else {
-        config::save_mcp_servers(&persisted).await
+        config::save_mcp_servers(servers).await
     }
 }
 
@@ -726,84 +641,10 @@ async fn get_secrets_store() -> anyhow::Result<Arc<dyn SecretsStore + Send + Syn
     crate::cli::init_secrets_store().await
 }
 
-fn as_settings_store(db: Option<&dyn Database>) -> Option<&(dyn crate::db::SettingsStore + Sync)> {
-    db.map(|db| db as &(dyn crate::db::SettingsStore + Sync))
-}
-
-async fn resolve_llm_for_cli(
-    store: Option<&(dyn crate::db::SettingsStore + Sync)>,
-) -> Result<LlmConfig, crate::error::ConfigError> {
-    resolve_llm_for_cli_with_toml(store, None).await
-}
-
-async fn resolve_llm_for_cli_with_toml(
-    store: Option<&(dyn crate::db::SettingsStore + Sync)>,
-    toml_path: Option<&std::path::Path>,
-) -> Result<LlmConfig, crate::error::ConfigError> {
-    if let Some(store) = store {
-        let _ = dotenvy::dotenv();
-        crate::bootstrap::load_ironclaw_env();
-
-        let mut settings = match store.get_all_settings(DEFAULT_USER_ID).await {
-            Ok(map) => crate::settings::Settings::from_db_map(&map),
-            Err(e) => {
-                tracing::warn!(
-                    "Failed to load CLI settings from DB, falling back to defaults before env/TOML resolution: {}",
-                    e
-                );
-                crate::settings::Settings::default()
-            }
-        };
-
-        apply_cli_toml_overlay(&mut settings, toml_path)?;
-        return LlmConfig::resolve(&settings);
-    }
-
-    let settings = crate::config::load_bootstrap_settings(toml_path)?;
-    LlmConfig::resolve(&settings)
-}
-
-fn apply_cli_toml_overlay(
-    settings: &mut crate::settings::Settings,
-    explicit_path: Option<&std::path::Path>,
-) -> Result<(), crate::error::ConfigError> {
-    let path = explicit_path
-        .map(std::path::PathBuf::from)
-        .unwrap_or_else(crate::settings::Settings::default_toml_path);
-
-    match crate::settings::Settings::load_toml(&path) {
-        Ok(Some(toml_settings)) => {
-            settings.merge_from(&toml_settings);
-        }
-        Ok(None) => {
-            if explicit_path.is_some() {
-                return Err(crate::error::ConfigError::ParseError(format!(
-                    "Config file not found: {}",
-                    path.display()
-                )));
-            }
-        }
-        Err(e) => {
-            return Err(crate::error::ConfigError::ParseError(e));
-        }
-    }
-
-    Ok(())
-}
-
 #[cfg(test)]
 mod tests {
     use super::*;
 
-    use std::collections::HashMap;
-
-    use async_trait::async_trait;
-
-    use crate::error::DatabaseError;
-    use crate::history::SettingRow;
-    #[cfg(feature = "libsql")]
-    use tempfile::NamedTempFile;
-
     #[test]
     fn test_mcp_command_parsing() {
         // Just verify the command structure is valid
@@ -860,129 +701,4 @@ mod tests {
         assert!(result.is_err());
         assert!(result.unwrap_err().contains("invalid env var format"));
     }
-
-    #[cfg(feature = "libsql")]
-    #[allow(clippy::await_holding_lock)]
-    #[tokio::test]
-    async fn test_resolve_llm_for_cli_uses_db_backed_selected_model() {
-        struct MockSettingsStore {
-            settings: HashMap<String, serde_json::Value>,
-        }
-
-        #[async_trait]
-        impl crate::db::SettingsStore for MockSettingsStore {
-            async fn get_setting(
-                &self,
-                _user_id: &str,
-                key: &str,
-            ) -> Result<Option<serde_json::Value>, DatabaseError> {
-                Ok(self.settings.get(key).cloned())
-            }
-
-            async fn get_setting_full(
-                &self,
-                _user_id: &str,
-                _key: &str,
-            ) -> Result<Option<SettingRow>, DatabaseError> {
-                Ok(None)
-            }
-
-            async fn set_setting(
-                &self,
-                _user_id: &str,
-                _key: &str,
-                _value: &serde_json::Value,
-            ) -> Result<(), DatabaseError> {
-                Err(DatabaseError::Query("unused in test".to_string()))
-            }
-
-            async fn delete_setting(
-                &self,
-                _user_id: &str,
-                _key: &str,
-            ) -> Result<bool, DatabaseError> {
-                Err(DatabaseError::Query("unused in test".to_string()))
-            }
-
-            async fn list_settings(
-                &self,
-                _user_id: &str,
-            ) -> Result<Vec<SettingRow>, DatabaseError> {
-                Ok(Vec::new())
-            }
-
-            async fn get_all_settings(
-                &self,
-                _user_id: &str,
-            ) -> Result<HashMap<String, serde_json::Value>, DatabaseError> {
-                Ok(self.settings.clone())
-            }
-
-            async fn set_all_settings(
-                &self,
-                _user_id: &str,
-                _settings: &HashMap<String, serde_json::Value>,
-            ) -> Result<(), DatabaseError> {
-                Err(DatabaseError::Query("unused in test".to_string()))
-            }
-
-            async fn has_settings(&self, _user_id: &str) -> Result<bool, DatabaseError> {
-                Ok(!self.settings.is_empty())
-            }
-        }
-
-        struct EnvGuard(&'static str, Option<String>);
-
-        impl Drop for EnvGuard {
-            fn drop(&mut self) {
-                // SAFETY: Protected by ENV_MUTEX for the duration of the test.
-                unsafe {
-                    match &self.1 {
-                        Some(value) => std::env::set_var(self.0, value),
-                        None => std::env::remove_var(self.0),
-                    }
-                }
-            }
-        }
-
-        let _mutex = crate::config::helpers::ENV_MUTEX.lock().expect("env mutex");
-        let prev_backend = std::env::var("LLM_BACKEND").ok();
-        let prev_base_url = std::env::var("NEARAI_BASE_URL").ok();
-        let prev_auth_url = std::env::var("NEARAI_AUTH_URL").ok();
-        let prev_model = std::env::var("NEARAI_MODEL").ok();
-
-        // SAFETY: Protected by ENV_MUTEX for the duration of the test.
-        unsafe {
-            std::env::set_var("LLM_BACKEND", "");
-            std::env::set_var("NEARAI_BASE_URL", "http://127.0.0.1:11434/v1");
-            std::env::set_var("NEARAI_AUTH_URL", "http://127.0.0.1:11435");
-            std::env::set_var("NEARAI_MODEL", "");
-        }
-
-        let _backend_guard = EnvGuard("LLM_BACKEND", prev_backend);
-        let _base_url_guard = EnvGuard("NEARAI_BASE_URL", prev_base_url);
-        let _auth_url_guard = EnvGuard("NEARAI_AUTH_URL", prev_auth_url);
-        let _model_guard = EnvGuard("NEARAI_MODEL", prev_model);
-
-        let empty_toml = NamedTempFile::new().expect("temp toml");
-        let store = MockSettingsStore {
-            settings: HashMap::from([
-                ("llm_backend".to_string(), serde_json::json!("nearai")),
-                (
-                    "selected_model".to_string(),
-                    serde_json::json!("db-backed-nearai-model"),
-                ),
-            ]),
-        };
-
-        let llm = resolve_llm_for_cli_with_toml(Some(&store), Some(empty_toml.path()))
-            .await
-            .expect("resolve llm");
-        assert_eq!(llm.backend, "nearai");
-        assert_eq!(llm.nearai.model, "db-backed-nearai-model");
-
-        let companion =
-            config::derive_nearai_companion_mcp_server_from_llm(&llm).expect("derived companion");
-        assert_eq!(companion.url, "http://127.0.0.1:11434/mcp");
-    }
 }

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.
-    /// Kept as `gateway_token` for public API compatibility.
+    /// Gateway auth token for authenticating with the platform token exchange proxy.
     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/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
 //!
@@ -506,10 +507,6 @@ pub struct InstalledExtension {
     /// Whether this extension has an auth configuration (OAuth or manual token).
     #[serde(default)]
     pub has_auth: bool,
-    /// Whether this extension is derived from provider/runtime state instead of
-    /// being a user-managed persisted configuration.
-    #[serde(default)]
-    pub derived: bool,
     /// Whether this extension is installed locally (false = available in registry but not installed).
     #[serde(default = "default_true")]
     pub installed: bool,
@@ -940,7 +937,6 @@ mod tests {
         assert!(ext.installed, "installed should default to true");
         assert!(!ext.needs_setup, "needs_setup should default to false");
         assert!(!ext.has_auth);
-        assert!(!ext.derived);
         assert!(ext.tools.is_empty());
         assert!(ext.display_name.is_none());
         assert!(ext.description.is_none());
@@ -961,7 +957,6 @@ mod tests {
             tools: vec!["send_email".to_string(), "read_inbox".to_string()],
             needs_setup: true,
             has_auth: true,
-            derived: true,
             installed: false,
             activation_error: Some("token expired".to_string()),
             version: None,
@@ -971,7 +966,6 @@ mod tests {
         assert_eq!(json["description"], "Read and send emails");
         assert_eq!(json["url"], "https://gmail.example.com");
         assert_eq!(json["needs_setup"], true);
-        assert_eq!(json["derived"], true);
         assert_eq!(json["installed"], false);
         assert_eq!(json["activation_error"], "token expired");
 
@@ -979,7 +973,6 @@ mod tests {
         assert_eq!(back.name, "gmail");
         assert_eq!(back.tools.len(), 2);
         assert!(back.needs_setup);
-        assert!(back.derived);
         assert!(!back.installed);
         assert_eq!(back.activation_error.as_deref(), Some("token expired"));
     }

src/llm/mod.rs

@@ -21,7 +21,6 @@ pub mod failover;
 pub mod gemini_oauth;
 mod github_copilot;
 pub(crate) mod github_copilot_auth;
-pub mod nearai_auth;
 mod nearai_chat;
 pub mod oauth_helpers;
 pub mod openai_codex_provider;
@@ -54,7 +53,6 @@ pub use config::{
 pub use error::LlmError;
 pub use failover::{CooldownConfig, FailoverProvider};
 pub use gemini_oauth::GeminiOauthProvider;
-pub use nearai_auth::{resolve_nearai_bearer_token, resolve_nearai_bearer_token_if_available};
 pub use nearai_chat::{DEFAULT_MODEL, ModelInfo, NearAiChatProvider, default_models};
 pub use openai_codex_provider::OpenAiCodexProvider;
 pub use openai_codex_session::{OpenAiCodexSession, OpenAiCodexSessionManager};

src/llm/nearai_auth.rs

@@ -1,95 +0,0 @@
-use secrecy::{ExposeSecret, SecretString};
-
-use crate::llm::LlmError;
-use crate::llm::session::SessionManager;
-
-/// Resolve the active NEAR AI bearer token only if already available.
-///
-/// Unlike [`resolve_nearai_bearer_token`], this helper is side-effect free:
-/// it never triggers an interactive login flow.
-pub async fn resolve_nearai_bearer_token_if_available(
-    api_key: Option<&SecretString>,
-    session: &SessionManager,
-) -> Result<Option<String>, LlmError> {
-    if let Some(api_key) = api_key {
-        return Ok(Some(api_key.expose_secret().to_string()));
-    }
-
-    if session.has_token().await {
-        let token = session.get_token().await?;
-        return Ok(Some(token.expose_secret().to_string()));
-    }
-
-    if let Some(key) = crate::config::helpers::env_or_override("NEARAI_API_KEY") {
-        return Ok(Some(key));
-    }
-
-    Ok(None)
-}
-
-/// Resolve the active NEAR AI bearer token.
-///
-/// Priority order:
-/// 1. Explicit API key from resolved config
-/// 2. Existing session token
-/// 3. Interactive session authentication
-/// 4. `NEARAI_API_KEY` from runtime environment
-pub async fn resolve_nearai_bearer_token(
-    api_key: Option<&SecretString>,
-    session: &SessionManager,
-) -> Result<String, LlmError> {
-    if let Some(token) = resolve_nearai_bearer_token_if_available(api_key, session).await? {
-        return Ok(token);
-    }
-
-    session.ensure_authenticated().await?;
-
-    if let Some(token) = resolve_nearai_bearer_token_if_available(api_key, session).await? {
-        return Ok(token);
-    }
-
-    Err(LlmError::AuthFailed {
-        provider: "nearai".to_string(),
-    })
-}
-
-#[cfg(test)]
-mod tests {
-    use super::*;
-    use crate::config::helpers::{ENV_MUTEX, set_runtime_env};
-    use crate::llm::session::SessionConfig;
-
-    struct EnvGuard(&'static str, Option<String>);
-
-    impl Drop for EnvGuard {
-        fn drop(&mut self) {
-            // SAFETY: tests hold ENV_MUTEX while mutating the process environment.
-            unsafe {
-                match &self.1 {
-                    Some(value) => std::env::set_var(self.0, value),
-                    None => std::env::remove_var(self.0),
-                }
-            }
-            set_runtime_env(self.0, "");
-        }
-    }
-
-    #[allow(clippy::await_holding_lock)]
-    #[tokio::test]
-    async fn test_resolve_bearer_token_if_available_uses_runtime_env_override() {
-        let _guard = ENV_MUTEX.lock().expect("env mutex");
-        let prev = std::env::var("NEARAI_API_KEY").ok();
-        // SAFETY: tests hold ENV_MUTEX while mutating the process environment.
-        unsafe { std::env::remove_var("NEARAI_API_KEY") };
-        let _env_guard = EnvGuard("NEARAI_API_KEY", prev);
-
-        set_runtime_env("NEARAI_API_KEY", "runtime-overlay-key");
-        let session = SessionManager::new(SessionConfig::default());
-
-        let token = resolve_nearai_bearer_token_if_available(None, &session)
-            .await
-            .expect("resolve token");
-
-        assert_eq!(token.as_deref(), Some("runtime-overlay-key"));
-    }
-}

src/llm/nearai_chat.rs

@@ -173,7 +173,36 @@ impl NearAiChatProvider {
     /// The env var fallback (#3) only triggers after `ensure_authenticated()`
     /// runs, because `api_key_login()` sets the env var but not a session token.
     async fn resolve_bearer_token(&self) -> Result<String, LlmError> {
-        crate::llm::resolve_nearai_bearer_token(self.config.api_key.as_ref(), &self.session).await
+        // 1. Config-level API key takes priority
+        if let Some(ref api_key) = self.config.api_key {
+            return Ok(api_key.expose_secret().to_string());
+        }
+
+        // 2. Existing session token (OAuth was already completed)
+        if self.session.has_token().await {
+            let token = self.session.get_token().await?;
+            return Ok(token.expose_secret().to_string());
+        }
+
+        // No token yet, trigger interactive login
+        self.session.ensure_authenticated().await?;
+
+        // 3. After login, check if a session token was stored (OAuth path)
+        if self.session.has_token().await {
+            let token = self.session.get_token().await?;
+            return Ok(token.expose_secret().to_string());
+        }
+
+        // 4. api_key_login() sets NEARAI_API_KEY env var but not a session token
+        if let Ok(key) = std::env::var("NEARAI_API_KEY")
+            && !key.is_empty()
+        {
+            return Ok(key);
+        }
+
+        Err(LlmError::AuthFailed {
+            provider: "nearai".to_string(),
+        })
     }
 
     /// Send a single request to the chat completions API.

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. \
-         When users ask about connecting a messaging platform, search for it as a channel.\n\
+         - **Channels** (Telegram, Slack, Discord) — connect messaging platforms so users can \
+         talk to you there. When users ask about connecting a messaging platform, search for it \
+         as a channel. Channels are not separate send-message tools; use normal assistant output \
+         to reply in the current conversation, and use the `message` tool only for proactive, \
+         background, or cross-channel outbound sends.\n\
          - **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\
-- Send file here: {\"content\": \"Here's the file\", \"attachments\": [\"/path/to/file.txt\"]}\n\
+- Proactive follow-up here: {\"content\": \"Hi again!\"}\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/autonomy.rs

@@ -139,8 +139,6 @@ mod tests {
         Arc::new(ExtensionManager::new(
             Arc::new(McpSessionManager::new()),
             Arc::new(McpProcessManager::new()),
-            None,
-            None,
             secrets,
             tools,
             Some(Arc::new(HookRegistry::default())),
@@ -150,7 +148,6 @@ mod tests {
             None,
             owner_id.to_string(),
             None,
-            None,
             Vec::new(),
         ))
     }

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. \
-         Use discover:true to search online if the built-in registry has no results."
+         channels (Telegram, Slack, Discord — connect messaging platforms so IronClaw can \
+         receive and reply there), tools, and MCP servers. Use `tool_install` and \
+         `tool_activate` to install and enable channels; use the `message` tool for proactive \
+         outbound sends. Use discover:true to search online if the built-in registry has no \
+         results."
     }
 
     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;
@@ -800,8 +814,6 @@ mod tests {
         Arc::new(ExtensionManager::new(
             Arc::new(McpSessionManager::new()),
             Arc::new(crate::tools::mcp::process::McpProcessManager::new()),
-            None,
-            None,
             Arc::new(InMemorySecretsStore::new(crypto)),
             Arc::new(ToolRegistry::new()),
             None,
@@ -811,7 +823,6 @@ mod tests {
             None,
             "test".to_string(),
             None,
-            None,
             Vec::new(),
         ))
     }

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 \
-         channel and sender/group. Use to proactively message users on any connected channel. \
+        "Send a proactive message to a channel. Use normal assistant output to reply in the \
+         active conversation; use this tool for proactive notifications, routine/background \
+         follow-ups, attachments, or sending to a different channel/recipient. If channel/target \
+         are omitted, reuses the current conversation's channel and sender/group when available. \
+         If you provide `target` without `channel` and no scoped channel can be resolved, the \
+         message may be broadcast across connected channels instead of sent to just one. \
          Supports file attachments: first download the file with the http tool using save_to \
-         (e.g., http GET https://picsum.photos/800/600 save_to=/tmp/photo.jpg), then pass \
-         the file path in the attachments array. Images are sent as photos on Telegram. \
+         (e.g., http GET https://picsum.photos/800/600 save_to=/tmp/photo.jpg), then pass the \
+         file path in the attachments array. Images are sent as photos on Telegram. \
          - Signal: target accepts E.164 (+1234567890) or group ID \
          - Telegram: target accepts username or chat ID \
          - Slack: target accepts channel (#general) or user ID"
@@ -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()) {
-            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 name = require_str(&params, "name")?;
 
         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

@@ -8,13 +8,12 @@ use std::sync::Arc;
 use std::sync::atomic::{AtomicU64, Ordering};
 
 use async_trait::async_trait;
-use secrecy::SecretString;
 use tokio::sync::RwLock;
 
 use crate::context::JobContext;
 use crate::secrets::SecretsStore;
 use crate::tools::mcp::auth::refresh_access_token;
-use crate::tools::mcp::config::{McpAuthSource, McpServerConfig};
+use crate::tools::mcp::config::McpServerConfig;
 use crate::tools::mcp::http_transport::HttpMcpTransport;
 use crate::tools::mcp::protocol::{
     CallToolResult, InitializeResult, ListToolsResult, McpRequest, McpResponse, McpTool,
@@ -47,13 +46,6 @@ pub struct McpClient {
     /// Session manager (shared across clients).
     session_manager: Option<Arc<McpSessionManager>>,
 
-    /// NEAR AI auth/session manager for companion MCP servers that reuse the
-    /// active provider bearer token.
-    nearai_session_manager: Option<Arc<crate::llm::SessionManager>>,
-
-    /// Resolved NEAR AI API key for companion MCP servers.
-    nearai_api_key: Option<SecretString>,
-
     /// Secrets store for retrieving access tokens.
     secrets: Option<Arc<dyn SecretsStore + Send + Sync>>,
 
@@ -88,8 +80,6 @@ impl McpClient {
             next_id: AtomicU64::new(1),
             tools_cache: RwLock::new(None),
             session_manager: None,
-            nearai_session_manager: None,
-            nearai_api_key: None,
             secrets: None,
             user_id: "default".to_string(),
             server_config: None,
@@ -113,8 +103,6 @@ impl McpClient {
             next_id: AtomicU64::new(1),
             tools_cache: RwLock::new(None),
             session_manager: None,
-            nearai_session_manager: None,
-            nearai_api_key: None,
             secrets: None,
             user_id: "default".to_string(),
             server_config: None,
@@ -129,15 +117,7 @@ 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> {
-        config
-            .validate()
-            .map_err(|e| ToolError::InvalidParameters(e.to_string()))?;
         if !matches!(
             config.effective_transport(),
             crate::tools::mcp::config::EffectiveTransport::Http
@@ -159,8 +139,6 @@ impl McpClient {
             next_id: AtomicU64::new(1),
             tools_cache: RwLock::new(None),
             session_manager: None,
-            nearai_session_manager: None,
-            nearai_api_key: None,
             secrets: None,
             user_id: "default".to_string(),
             custom_headers: config.headers.clone(),
@@ -192,8 +170,6 @@ impl McpClient {
             next_id: AtomicU64::new(1),
             tools_cache: RwLock::new(None),
             session_manager: Some(session_manager),
-            nearai_session_manager: None,
-            nearai_api_key: None,
             secrets: Some(secrets),
             user_id: user_id.into(),
             server_config: Some(config),
@@ -230,8 +206,6 @@ impl McpClient {
             next_id: AtomicU64::new(1),
             tools_cache: RwLock::new(None),
             session_manager,
-            nearai_session_manager: None,
-            nearai_api_key: None,
             secrets,
             user_id: user_id.into(),
             server_config,
@@ -240,34 +214,12 @@ impl McpClient {
         }
     }
 
-    /// Attach a session manager to the **client** only.
-    ///
-    /// **Warning:** This does NOT wire the session manager into the underlying
-    /// `HttpMcpTransport`, so the transport will not capture `Mcp-Session-Id`
-    /// from responses. For production use, construct the transport with
-    /// `HttpMcpTransport::with_session_manager()` and pass it to
-    /// `new_with_transport()` instead. See `create_client_from_config()`.
-    #[cfg(test)]
+    /// Attach a session manager for Streamable HTTP session tracking.
     pub fn with_session_manager(mut self, session_manager: Arc<McpSessionManager>) -> Self {
         self.session_manager = Some(session_manager);
         self
     }
 
-    /// Attach the NEAR AI session manager for companion MCP auth reuse.
-    pub fn with_nearai_session_manager(
-        mut self,
-        nearai_session_manager: Arc<crate::llm::SessionManager>,
-    ) -> Self {
-        self.nearai_session_manager = Some(nearai_session_manager);
-        self
-    }
-
-    /// Attach the resolved NEAR AI API key for companion MCP auth reuse.
-    pub fn with_nearai_api_key(mut self, nearai_api_key: Option<SecretString>) -> Self {
-        self.nearai_api_key = nearai_api_key;
-        self
-    }
-
     /// Get the server name.
     pub fn server_name(&self) -> &str {
         &self.server_name
@@ -283,12 +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)
@@ -302,9 +248,6 @@ impl McpClient {
         let Some(ref config) = self.server_config else {
             return Ok(None);
         };
-        if config.uses_runtime_auth_source() {
-            return Ok(None);
-        }
         match secrets
             .get_decrypted(&self.user_id, &config.token_secret_name())
             .await
@@ -318,36 +261,6 @@ impl McpClient {
         }
     }
 
-    /// Resolve a runtime-provided auth token for companion MCP servers.
-    async fn get_runtime_auth_token(&self) -> Result<Option<String>, ToolError> {
-        let Some(ref config) = self.server_config else {
-            return Ok(None);
-        };
-
-        match config.auth_source {
-            Some(McpAuthSource::NearAi) => {
-                let Some(ref session_manager) = self.nearai_session_manager else {
-                    return Err(ToolError::ExternalService(
-                        "Missing NEAR AI session manager for companion MCP server".to_string(),
-                    ));
-                };
-
-                crate::llm::resolve_nearai_bearer_token_if_available(
-                    self.nearai_api_key.as_ref(),
-                    session_manager,
-                )
-                .await
-                .map_err(|e| {
-                    ToolError::ExternalService(format!(
-                        "Failed to resolve NEAR AI token for MCP server '{}': {}",
-                        self.server_name, e
-                    ))
-                })
-            }
-            None => Ok(None),
-        }
-    }
-
     /// Build the headers map for a request (auth, session-id, custom headers).
     ///
     /// Custom headers are applied first. OAuth token injection is skipped if the
@@ -361,9 +274,6 @@ impl McpClient {
             .custom_headers
             .keys()
             .any(|k| k.eq_ignore_ascii_case("authorization"));
-        if !has_custom_auth && let Some(token) = self.get_runtime_auth_token().await? {
-            headers.insert("Authorization".to_string(), format!("Bearer {}", token));
-        }
         if !has_custom_auth && let Some(token) = self.get_access_token().await? {
             let trimmed = token.trim();
             if !trimmed.is_empty() {
@@ -584,12 +494,13 @@ impl McpClient {
             )));
         }
 
-        let raw_result = response
+        response
             .result
-            .ok_or_else(|| ToolError::ExternalService("No result in MCP response".to_string()))?;
-
-        serde_json::from_value(raw_result)
-            .map_err(|e| ToolError::ExternalService(format!("Invalid tool result: {}", e)))
+            .ok_or_else(|| ToolError::ExternalService("No result in MCP response".to_string()))
+            .and_then(|r| {
+                serde_json::from_value(r)
+                    .map_err(|e| ToolError::ExternalService(format!("Invalid tool result: {}", e)))
+            })
     }
 
     /// Clear the tools cache.
@@ -636,8 +547,6 @@ impl Clone for McpClient {
             next_id: AtomicU64::new(self.next_id.load(Ordering::SeqCst)),
             tools_cache: RwLock::new(None),
             session_manager: self.session_manager.clone(),
-            nearai_session_manager: self.nearai_session_manager.clone(),
-            nearai_api_key: self.nearai_api_key.clone(),
             secrets: self.secrets.clone(),
             user_id: self.user_id.clone(),
             server_config: self.server_config.clone(),
@@ -685,7 +594,7 @@ impl Tool for McpToolWrapper {
         // Strip top-level null values before forwarding — LLMs often emit
         // `"field": null` for optional params, but many MCP servers reject
         // explicit nulls for fields that should simply be absent.
-        let params = normalize_mcp_tool_arguments(&self.tool.name, strip_top_level_nulls(params));
+        let params = strip_top_level_nulls(params);
 
         let result = self.client.call_tool(&self.tool.name, params).await?;
         let content: String = result
@@ -729,31 +638,6 @@ fn strip_top_level_nulls(value: serde_json::Value) -> serde_json::Value {
     }
 }
 
-fn normalize_mcp_tool_arguments(tool_name: &str, value: serde_json::Value) -> serde_json::Value {
-    if tool_name != "web_search" {
-        return value;
-    }
-
-    let serde_json::Value::Object(mut map) = value else {
-        return value;
-    };
-
-    // Keep this intentionally narrow: only strip optional fields that the
-    // model frequently emits as empty strings. Provider-specific validation
-    // should remain server-side, and tighter constraints should come from the
-    // tool schema rather than client-side normalization.
-    map.retain(|key, value| match key.as_str() {
-        // Only strip known optional string fields. Never remove required
-        // fields like `query`, even when the model emits an empty string.
-        "country" | "freshness" | "goggles" | "result_filter" | "search_lang" | "ui_lang" => {
-            !value.as_str().is_some_and(|s| s.trim().is_empty())
-        }
-        _ => true,
-    });
-
-    serde_json::Value::Object(map)
-}
-
 #[cfg(test)]
 mod tests {
     use super::*;
@@ -921,138 +805,6 @@ mod tests {
         assert!(client.has_session_manager());
     }
 
-    #[tokio::test]
-    async fn test_build_request_headers_with_nearai_runtime_auth() {
-        use crate::llm::{
-            SessionConfig as NearAiSessionConfig, SessionManager as NearAiSessionManager,
-        };
-        use secrecy::SecretString;
-
-        let config = McpServerConfig::new(
-            crate::tools::mcp::config::NEARAI_COMPANION_MCP_NAME,
-            "http://localhost:3000/mcp",
-        )
-        .with_auth_source(crate::tools::mcp::config::McpAuthSource::NearAi);
-        let nearai_session = Arc::new(NearAiSessionManager::new(NearAiSessionConfig::default()));
-        nearai_session
-            .set_token(SecretString::from("sess_test_token"))
-            .await;
-
-        let client = McpClient::new_with_config(config)
-            .expect("valid MCP config")
-            .with_nearai_session_manager(nearai_session);
-        let headers = client.build_request_headers().await.expect("headers");
-
-        assert_eq!(
-            headers.get("Authorization").map(String::as_str),
-            Some("Bearer sess_test_token")
-        );
-    }
-
-    #[tokio::test]
-    async fn test_build_request_headers_without_nearai_auth_does_not_trigger_login() {
-        use crate::llm::{
-            SessionConfig as NearAiSessionConfig, SessionManager as NearAiSessionManager,
-        };
-
-        let config = McpServerConfig::new(
-            crate::tools::mcp::config::NEARAI_COMPANION_MCP_NAME,
-            "http://localhost:3000/mcp",
-        )
-        .with_auth_source(crate::tools::mcp::config::McpAuthSource::NearAi);
-        let nearai_session = Arc::new(NearAiSessionManager::new(NearAiSessionConfig::default()));
-
-        let client = McpClient::new_with_config(config)
-            .expect("valid MCP config")
-            .with_nearai_session_manager(nearai_session);
-        let headers = client.build_request_headers().await.expect("headers");
-
-        assert!(
-            !headers.contains_key("Authorization"),
-            "runtime auth should stay absent when no token is available"
-        );
-    }
-
-    #[tokio::test]
-    async fn test_build_request_headers_runtime_auth_ignores_persisted_mcp_token() {
-        use crate::llm::{
-            SessionConfig as NearAiSessionConfig, SessionManager as NearAiSessionManager,
-        };
-        use crate::secrets::{CreateSecretParams, DecryptedSecret, Secret, SecretError, SecretRef};
-        use secrecy::SecretString;
-        use uuid::Uuid;
-
-        struct PersistedTokenStore;
-
-        #[async_trait]
-        impl crate::secrets::SecretsStore for PersistedTokenStore {
-            async fn create(
-                &self,
-                _user_id: &str,
-                _params: CreateSecretParams,
-            ) -> Result<Secret, SecretError> {
-                unimplemented!()
-            }
-            async fn get(&self, _user_id: &str, _name: &str) -> Result<Secret, SecretError> {
-                unimplemented!()
-            }
-            async fn get_decrypted(
-                &self,
-                _user_id: &str,
-                _name: &str,
-            ) -> Result<DecryptedSecret, SecretError> {
-                DecryptedSecret::from_bytes(b"persisted-mcp-token".to_vec())
-            }
-            async fn exists(&self, _user_id: &str, _name: &str) -> Result<bool, SecretError> {
-                Ok(true)
-            }
-            async fn delete(&self, _user_id: &str, _name: &str) -> Result<bool, SecretError> {
-                Ok(true)
-            }
-            async fn list(&self, _user_id: &str) -> Result<Vec<SecretRef>, SecretError> {
-                Ok(Vec::new())
-            }
-            async fn record_usage(&self, _secret_id: Uuid) -> Result<(), SecretError> {
-                Ok(())
-            }
-            async fn is_accessible(
-                &self,
-                _user_id: &str,
-                _secret_name: &str,
-                _allowed_secrets: &[String],
-            ) -> Result<bool, SecretError> {
-                Ok(true)
-            }
-        }
-
-        let config = McpServerConfig::new(
-            crate::tools::mcp::config::NEARAI_COMPANION_MCP_NAME,
-            "http://localhost:3000/mcp",
-        )
-        .with_auth_source(crate::tools::mcp::config::McpAuthSource::NearAi);
-        let nearai_session = Arc::new(NearAiSessionManager::new(NearAiSessionConfig::default()));
-        nearai_session
-            .set_token(SecretString::from("sess_runtime_token"))
-            .await;
-
-        let secrets: Arc<dyn crate::secrets::SecretsStore + Send + Sync> =
-            Arc::new(PersistedTokenStore);
-        let client = McpClient::new_authenticated(
-            config,
-            Arc::new(McpSessionManager::new()),
-            secrets,
-            "test-user",
-        )
-        .with_nearai_session_manager(nearai_session);
-        let headers = client.build_request_headers().await.expect("headers");
-
-        assert_eq!(
-            headers.get("Authorization").map(String::as_str),
-            Some("Bearer sess_runtime_token"),
-            "runtime auth must win even if a persisted MCP token exists"
-        );
-    }
-
     #[test]
     fn test_next_request_id_monotonically_increasing() {
         let client = McpClient::new("http://localhost:1234");
@@ -1434,20 +1186,6 @@ mod tests {
         );
     }
 
-    #[test]
-    fn test_new_with_config_rejects_invalid_runtime_auth_name() {
-        let config = McpServerConfig::new("chat_api", "http://localhost:3000/mcp")
-            .with_auth_source(crate::tools::mcp::config::McpAuthSource::NearAi);
-        let err = match McpClient::new_with_config(config) {
-            Ok(_) => panic!("invalid runtime-auth config must be rejected"),
-            Err(err) => err.to_string(),
-        };
-        assert!(
-            err.contains(crate::tools::mcp::config::NEARAI_COMPANION_MCP_NAME),
-            "error should mention reserved companion requirement: {err}"
-        );
-    }
-
     // --- Issue 13: McpToolWrapper unit tests ---
 
     fn make_test_mcp_tool(destructive: bool) -> McpTool {
@@ -1678,63 +1416,4 @@ mod tests {
             "Token must be trimmed before use in Authorization header"
         );
     }
-
-    #[test]
-    fn test_normalize_web_search_arguments_removes_empty_optional_fields() {
-        let input = serde_json::json!({
-            "query": "Rust MCP server example",
-            "goggles": "",
-            "result_filter": "   ",
-            "ui_lang": "en-US"
-        });
-
-        let result = normalize_mcp_tool_arguments("web_search", input);
-        let obj = result.as_object().unwrap();
-        assert_eq!(obj["query"], "Rust MCP server example");
-        assert_eq!(obj["ui_lang"], "en-US");
-        assert!(!obj.contains_key("goggles"));
-        assert!(!obj.contains_key("result_filter"));
-    }
-
-    #[test]
-    fn test_normalize_web_search_arguments_strips_whitelisted_empty_optional_fields() {
-        let input = serde_json::json!({
-            "query": "Rust MCP server example",
-            "goggles": "",
-            "freshness": "   ",
-            "country": "US"
-        });
-
-        let result = normalize_mcp_tool_arguments("web_search", input);
-        let obj = result.as_object().unwrap();
-        assert_eq!(obj["country"], "US");
-        assert!(!obj.contains_key("freshness"));
-        assert!(!obj.contains_key("goggles"));
-    }
-
-    #[test]
-    fn test_normalize_web_search_arguments_preserves_empty_required_query() {
-        let input = serde_json::json!({
-            "query": "   ",
-            "goggles": "",
-            "country": "US"
-        });
-
-        let result = normalize_mcp_tool_arguments("web_search", input);
-        let obj = result.as_object().unwrap();
-        assert_eq!(obj["query"], "   ");
-        assert_eq!(obj["country"], "US");
-        assert!(!obj.contains_key("goggles"));
-    }
-
-    #[test]
-    fn test_normalize_mcp_tool_arguments_leaves_other_tools_unchanged() {
-        let input = serde_json::json!({
-            "goggles": "",
-            "country": "us"
-        });
-
-        let result = normalize_mcp_tool_arguments("other_tool", input.clone());
-        assert_eq!(result, input);
-    }
 }

src/tools/mcp/config.rs

@@ -51,16 +51,6 @@ pub struct McpServerConfig {
     #[serde(skip_serializing_if = "Option::is_none")]
     pub oauth: Option<OAuthConfig>,
 
-    /// Built-in auth source provided by IronClaw at runtime.
-    ///
-    /// This is used for companion MCP servers that should reuse an existing
-    /// provider identity instead of running their own MCP OAuth flow.
-    ///
-    /// Security: this field is runtime-only. Persisted user config must not be
-    /// able to opt a server into reusing the active provider bearer token.
-    #[serde(default, skip_serializing, skip_deserializing)]
-    pub auth_source: Option<McpAuthSource>,
-
     /// Whether this server is enabled.
     #[serde(default = "default_true")]
     pub enabled: bool,
@@ -70,14 +60,6 @@ pub struct McpServerConfig {
     pub description: Option<String>,
 }
 
-/// Runtime-provided auth sources for MCP companion servers.
-#[derive(Debug, Clone, Serialize, Deserialize, PartialEq, Eq)]
-#[serde(rename_all = "snake_case")]
-pub enum McpAuthSource {
-    /// Reuse the active NEAR AI bearer token (session token or API key).
-    NearAi,
-}
-
 fn default_true() -> bool {
     true
 }
@@ -91,7 +73,6 @@ impl McpServerConfig {
             transport: None,
             headers: HashMap::new(),
             oauth: None,
-            auth_source: None,
             enabled: true,
             description: None,
         }
@@ -114,7 +95,6 @@ impl McpServerConfig {
             }),
             headers: HashMap::new(),
             oauth: None,
-            auth_source: None,
             enabled: true,
             description: None,
         }
@@ -130,7 +110,6 @@ impl McpServerConfig {
             }),
             headers: HashMap::new(),
             oauth: None,
-            auth_source: None,
             enabled: true,
             description: None,
         }
@@ -142,12 +121,6 @@ impl McpServerConfig {
         self
     }
 
-    /// Set a runtime-provided auth source.
-    pub fn with_auth_source(mut self, auth_source: McpAuthSource) -> Self {
-        self.auth_source = Some(auth_source);
-        self
-    }
-
     /// Set description.
     pub fn with_description(mut self, description: impl Into<String>) -> Self {
         self.description = Some(description.into());
@@ -181,15 +154,6 @@ impl McpServerConfig {
             });
         }
 
-        if self.uses_runtime_auth_source() && !is_nearai_companion_server_name(&self.name) {
-            return Err(ConfigError::InvalidConfig {
-                reason: format!(
-                    "Runtime auth source is only allowed for reserved server '{}'",
-                    NEARAI_COMPANION_MCP_NAME
-                ),
-            });
-        }
-
         match self.effective_transport() {
             EffectiveTransport::Http => {
                 if self.url.is_empty() {
@@ -258,11 +222,6 @@ impl McpServerConfig {
             .any(|k| k.eq_ignore_ascii_case("authorization"))
     }
 
-    /// Check if this server uses a built-in runtime auth bridge.
-    pub fn uses_runtime_auth_source(&self) -> bool {
-        self.auth_source.is_some()
-    }
-
     /// Check if this server requires authentication.
     ///
     /// Returns true if OAuth is pre-configured OR if this is a remote HTTPS server
@@ -275,7 +234,7 @@ impl McpServerConfig {
             return false;
         }
 
-        if self.oauth.is_some() || self.uses_runtime_auth_source() {
+        if self.oauth.is_some() {
             return true;
         }
         // Remote HTTPS servers need auth handling (DCR, token refresh, 401 detection).
@@ -301,66 +260,6 @@ impl McpServerConfig {
     }
 }
 
-/// Reserved name used for the companion MCP server derived from active NEAR AI config.
-pub const NEARAI_COMPANION_MCP_NAME: &str = "_nearai_companion_mcp";
-
-pub fn is_nearai_companion_server_name(name: &str) -> bool {
-    name == NEARAI_COMPANION_MCP_NAME
-}
-
-fn strip_reserved_nearai_companion_servers(config: &mut McpServersFile, source: &str) -> usize {
-    let len_before = config.servers.len();
-    config
-        .servers
-        .retain(|server| !is_nearai_companion_server_name(&server.name));
-    let removed = len_before.saturating_sub(config.servers.len());
-
-    if removed > 0 {
-        tracing::warn!(
-            count = removed,
-            source,
-            "Ignoring persisted reserved MCP companion config(s); this name is system-managed"
-        );
-    }
-
-    removed
-}
-
-/// Build the companion MCP server from the active NEAR AI config.
-///
-/// The MCP endpoint is treated as a sibling to the versioned REST API:
-/// `https://host/v1` becomes `https://host/mcp`.
-pub fn derive_nearai_companion_mcp_server(
-    config: &crate::config::Config,
-) -> Option<McpServerConfig> {
-    derive_nearai_companion_mcp_server_from_llm(&config.llm)
-}
-
-/// Build the companion MCP server from an LLM config.
-///
-/// This lighter-weight helper is used by CLI code paths that should not need
-/// to resolve the full application config (and therefore should not require
-/// database configuration) just to discover the derived companion MCP server.
-pub fn derive_nearai_companion_mcp_server_from_llm(
-    llm: &crate::config::LlmConfig,
-) -> Option<McpServerConfig> {
-    if llm.backend != "nearai" {
-        return None;
-    }
-
-    let base = llm.nearai.base_url.trim_end_matches('/');
-    let mcp_base = base
-        .strip_suffix("/v1")
-        .unwrap_or(base)
-        .trim_end_matches('/');
-
-    Some(
-        McpServerConfig::new(NEARAI_COMPANION_MCP_NAME, format!("{mcp_base}/mcp"))
-            .with_auth_source(McpAuthSource::NearAi)
-            .with_description("Companion MCP server derived from the active NEAR AI provider"),
-    )
-}
-
 /// OAuth 2.1 configuration for an MCP server.
 #[derive(Debug, Clone, Serialize, Deserialize)]
 pub struct OAuthConfig {
@@ -457,16 +356,6 @@ impl McpServersFile {
         }
     }
 
-    /// Insert a server only if no server with the same name already exists.
-    pub fn insert_if_absent(&mut self, config: McpServerConfig) -> bool {
-        if self.get(&config.name).is_some() {
-            false
-        } else {
-            self.servers.push(config);
-            true
-        }
-    }
-
     /// Remove a server by name.
     pub fn remove(&mut self, name: &str) -> bool {
         let len_before = self.servers.len();
@@ -521,8 +410,7 @@ pub async fn load_mcp_servers_from(path: impl AsRef<Path>) -> Result<McpServersF
     }
 
     let content = fs::read_to_string(path).await?;
-    let mut config: McpServersFile = serde_json::from_str(&content)?;
-    strip_reserved_nearai_companion_servers(&mut config, &path.display().to_string());
+    let config: McpServersFile = serde_json::from_str(&content)?;
 
     // Validate every server on load so corrupted configs are caught early
     for server in &config.servers {
@@ -564,15 +452,6 @@ pub async fn save_mcp_servers_to(
 
 /// Add a new MCP server configuration.
 pub async fn add_mcp_server(config: McpServerConfig) -> Result<(), ConfigError> {
-    if is_nearai_companion_server_name(&config.name) {
-        return Err(ConfigError::InvalidConfig {
-            reason: format!(
-                "Server name '{}' is reserved for the NEAR AI companion MCP server",
-                config.name
-            ),
-        });
-    }
-
     config.validate()?;
 
     let mut servers = load_mcp_servers().await?;
@@ -620,8 +499,7 @@ pub async fn load_mcp_servers_from_db(
 ) -> Result<McpServersFile, ConfigError> {
     match store.get_setting(user_id, "mcp_servers").await {
         Ok(Some(value)) => {
-            let mut config: McpServersFile = serde_json::from_value(value)?;
-            strip_reserved_nearai_companion_servers(&mut config, "database");
+            let config: McpServersFile = serde_json::from_value(value)?;
             // Validate every server on load so corrupted DB configs are caught early
             for server in &config.servers {
                 server.validate().map_err(|e| ConfigError::InvalidConfig {
@@ -664,15 +542,6 @@ pub async fn add_mcp_server_db(
     user_id: &str,
     config: McpServerConfig,
 ) -> Result<(), ConfigError> {
-    if is_nearai_companion_server_name(&config.name) {
-        return Err(ConfigError::InvalidConfig {
-            reason: format!(
-                "Server name '{}' is reserved for the NEAR AI companion MCP server",
-                config.name
-            ),
-        });
-    }
-
     config.validate()?;
 
     let mut servers = load_mcp_servers_from_db(store, user_id).await?;
@@ -849,69 +718,6 @@ mod tests {
         assert!(config.servers.is_empty());
     }
 
-    #[tokio::test]
-    async fn test_load_drops_reserved_nearai_companion_server() {
-        let dir = tempdir().unwrap();
-        let path = dir.path().join("mcp-servers.json");
-
-        let persisted = serde_json::json!({
-            "servers": [
-                {
-                    "name": NEARAI_COMPANION_MCP_NAME,
-                    "url": "https://evil.example.com/mcp",
-                    "enabled": true,
-                    "auth_source": "near_ai"
-                },
-                {
-                    "name": "notion",
-                    "url": "https://mcp.notion.com",
-                    "enabled": true
-                }
-            ]
-        });
-        tokio::fs::write(&path, persisted.to_string())
-            .await
-            .unwrap();
-
-        let config = load_mcp_servers_from(&path).await.unwrap();
-        assert_eq!(config.servers.len(), 1);
-        assert!(config.get(NEARAI_COMPANION_MCP_NAME).is_none());
-        assert_eq!(
-            config.get("notion").map(|server| server.url.as_str()),
-            Some("https://mcp.notion.com")
-        );
-    }
-
-    #[test]
-    fn test_deserialize_ignores_persisted_auth_source() {
-        let raw = serde_json::json!({
-            "name": "user-managed",
-            "url": "https://mcp.example.com",
-            "enabled": true,
-            "auth_source": "near_ai"
-        });
-
-        let server: McpServerConfig = serde_json::from_value(raw).expect("server");
-        assert_eq!(server.auth_source, None);
-    }
-
-    #[cfg(feature = "libsql")]
-    #[test]
-    fn test_derive_nearai_companion_mcp_server_strips_trailing_v1() {
-        let mut config = crate::config::Config::for_testing(
-            std::env::temp_dir().join("ironclaw-test-companion.db"),
-            std::env::temp_dir().join("ironclaw-test-skills"),
-            std::env::temp_dir().join("ironclaw-test-installed-skills"),
-        );
-        config.llm.backend = "nearai".to_string();
-        config.llm.nearai.base_url = "https://private.near.ai/v1".to_string();
-
-        let server = derive_nearai_companion_mcp_server(&config).expect("companion server");
-        assert_eq!(server.name, NEARAI_COMPANION_MCP_NAME);
-        assert_eq!(server.url, "https://private.near.ai/mcp");
-        assert_eq!(server.auth_source, Some(McpAuthSource::NearAi));
-    }
-
     #[tokio::test]
     async fn test_load_rejects_corrupted_headers() {
         let dir = tempdir().unwrap();
@@ -957,20 +763,6 @@ mod tests {
         assert!(config.requires_auth());
     }
 
-    #[test]
-    fn test_validate_rejects_runtime_auth_on_user_managed_server() {
-        let config = McpServerConfig::new("user-managed", "https://mcp.example.com")
-            .with_auth_source(McpAuthSource::NearAi);
-
-        let err = config
-            .validate()
-            .expect_err("runtime auth should be reserved for the companion server");
-        assert!(
-            err.to_string().contains(NEARAI_COMPANION_MCP_NAME),
-            "expected reserved-name validation message, got: {err}"
-        );
-    }
-
     #[test]
     fn test_requires_auth_remote_https_without_oauth() {
         // Remote HTTPS servers need auth even without pre-configured OAuth (DCR)

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.
@@ -21,8 +20,6 @@ pub enum McpFactoryError {
     UnixNotSupported { name: String },
     #[error("Invalid configuration for MCP server '{name}': {reason}")]
     InvalidConfig { name: String, reason: String },
-    #[error("Missing runtime auth context for MCP server '{name}': {reason}")]
-    MissingRuntimeAuthContext { name: String, reason: String },
 }
 
 /// Create an `McpClient` from a server configuration, dispatching on the
@@ -30,8 +27,6 @@ pub enum McpFactoryError {
 pub async fn create_client_from_config(
     server: McpServerConfig,
     session_manager: &Arc<McpSessionManager>,
-    nearai_session_manager: Option<Arc<crate::llm::SessionManager>>,
-    nearai_api_key: Option<secrecy::SecretString>,
     process_manager: &Arc<McpProcessManager>,
     secrets: Option<Arc<dyn SecretsStore + Send + Sync>>,
     user_id: &str,
@@ -83,61 +78,33 @@ pub async fn create_client_from_config(
             Err(McpFactoryError::UnixNotSupported { name: server_name })
         }
         EffectiveTransport::Http => {
-            if server.uses_runtime_auth_source() {
-                let nearai_session_manager = nearai_session_manager.ok_or_else(|| {
-                    McpFactoryError::MissingRuntimeAuthContext {
-                        name: server_name.clone(),
-                        reason: "NearAI companion MCP servers require a NearAI session manager"
-                            .to_string(),
-                    }
-                })?;
-
-                let transport = Arc::new(
-                    HttpMcpTransport::new(server.url.clone(), server.name.clone())
-                        .with_session_manager(Arc::clone(session_manager)),
-                );
-
-                return Ok(McpClient::new_with_transport(
-                    server.name.clone(),
-                    transport,
-                    Some(Arc::clone(session_manager)),
-                    secrets,
-                    user_id,
-                    Some(server),
-                )
-                .with_nearai_session_manager(nearai_session_manager)
-                .with_nearai_api_key(nearai_api_key));
-            }
             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,
-                    ));
+                    ))
+                } else {
+                    Ok(McpClient::new_with_config(server)
+                        .map_err(|e| McpFactoryError::InvalidConfig {
+                            name: server_name.clone(),
+                            reason: e.to_string(),
+                        })?
+                        .with_session_manager(Arc::clone(session_manager)))
                 }
+            } else {
+                Ok(McpClient::new_with_config(server)
+                    .map_err(|e| McpFactoryError::InvalidConfig {
+                        name: server_name,
+                        reason: e.to_string(),
+                    })?
+                    .with_session_manager(Arc::clone(session_manager)))
             }
-
-            // Non-OAuth HTTP: wire the session manager into the *transport* so
-            // it captures `Mcp-Session-Id` from responses. Passing it only to
-            // the client (via `with_session_manager`) is not enough — the
-            // transport must know about it to read/write the header.
-            let transport = Arc::new(
-                HttpMcpTransport::new(server.url.clone(), server.name.clone())
-                    .with_session_manager(Arc::clone(session_manager)),
-            );
-            Ok(McpClient::new_with_transport(
-                server.name.clone(),
-                transport,
-                Some(Arc::clone(session_manager)),
-                secrets,
-                user_id,
-                Some(server),
-            ))
         }
     }
 }
@@ -155,8 +122,6 @@ mod tests {
         let client = create_client_from_config(
             server,
             &session_manager,
-            None,
-            None,
             &process_manager,
             None,
             "test-user",
@@ -169,86 +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,
-            None,
-            None,
-            &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.
-    /// Kept as `gateway_token` for public API compatibility.
+    /// Gateway auth token for authenticating with the hosted OAuth proxy.
     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
-    // -----------------------------------------------------------------------
-
-    #[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
+    // Test 5: 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/e2e_routine_heartbeat.rs

@@ -290,8 +290,6 @@ mod tests {
         Arc::new(ExtensionManager::new(
             Arc::new(McpSessionManager::new()),
             Arc::new(McpProcessManager::new()),
-            None,
-            None,
             secrets,
             tools,
             None,
@@ -301,7 +299,6 @@ mod tests {
             None,
             owner_id.to_string(),
             None,
-            None,
             Vec::new(),
         ))
     }

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/module_init_integration.rs

@@ -203,8 +203,6 @@ async fn extension_manager_with_process_manager_constructs() {
     let manager = ExtensionManager::new(
         Arc::new(McpSessionManager::new()),
         Arc::new(McpProcessManager::new()),
-        None,
-        None,
         secrets,
         tools,
         None,
@@ -214,7 +212,6 @@ async fn extension_manager_with_process_manager_constructs() {
         None,
         "test".to_string(),
         None,
-        None,
         Vec::new(),
     );
 

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();
+    }
 }