feat(oauth): route callbacks through web gateway for hosted instances (#555)

* feat: route OAuth callbacks through web gateway for hosted instances

On hosted instances (e.g., NEAR AI), OAuth callbacks can't reach the
local TCP listener on port 9876. This adds a gateway-routed OAuth flow
that works behind reverse proxies and load balancers.

Backend changes:
- Add /oauth/callback as a public route on the web gateway
- PendingOAuthFlow registry shared between ExtensionManager and handler
- Gateway mode auto-detected via IRONCLAW_OAUTH_CALLBACK_URL env var
- Platform state format (instance:nonce) for nginx routing
- Token exchange proxy support via IRONCLAW_OAUTH_EXCHANGE_URL
- Local TCP listener mode preserved as backward-compatible fallback

UX improvements:
- Hide Configure button for tools with auto-resolved OAuth credentials
  (builtin defaults or platform-injected env vars)
- Skip client_id/client_secret fields in setup schema when auto-resolved
- Show Reconfigure only after successful authentication

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

* fix(oauth): harden gateway callback and refactor AuthResult

- Add 60s timeout to exchange_via_proxy HTTP client (matching exchange_oauth_code)
- Read GATEWAY_AUTH_TOKEN once at ExtensionManager construction instead of
  per-flow from env (prevents coupling and clarifies token provenance)
- Extract oauth_error_page() helper to deduplicate error landing pages
- Remove IRONCLAW_FORCE_GATEWAY_CALLBACK env var (auto-detection suffices)
- Refactor AuthResult into typed AuthStatus enum with constructors,
  eliminating stringly-typed status and Option fields that were always None
- Adapt all handlers (chat, extensions, ws) to new AuthResult/AuthStatus API
- Use setup_url (not validation_endpoint) for awaiting_token responses

[skip-regression-check]

Co-Authored-By: Claude Sonnet 4.6 <[email protected]>

* fix(oauth): address review feedback — empty token guard, test flakiness, doc typos

- Fail early in exchange_via_proxy() when gateway_token is empty instead
  of sending an unauthenticated request to the exchange proxy
- Fix test_oauth_callback_strips_instance_prefix to use an expired flow
  so it never attempts a real HTTP token exchange (prevents CI flakiness)
- Fix doc comments: /auth/callback → /oauth/callback in PendingOAuthFlow
  and ExtensionManager pending_oauth_flows docs

[skip-regression-check]

Co-Authored-By: Claude Sonnet 4.6 <[email protected]>

* fix: clarify strip_instance_prefix safety, wrapper credential fix, test assertion

- Add comment to strip_instance_prefix noting nonces are base64url (no colons)
- Expand wrapper.rs comment explaining the credential_user_id bug fix
- Fix test_oauth_callback_strips_instance_prefix assertion: landing_html
  does not include provider_name on error pages

[skip-regression-check]

Co-Authored-By: Claude Sonnet 4.6 <[email protected]>

---------

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

src/agent/thread_ops.rs

@@ -1295,7 +1295,7 @@ impl Agent {
         };
 
         match ext_mgr.auth(&pending.extension_name, Some(token)).await {
-            Ok(result) if result.status == "authenticated" => {
+            Ok(result) if result.is_authenticated() => {
                 tracing::info!(
                     "Extension '{}' authenticated via auth mode",
                     pending.extension_name
@@ -1364,8 +1364,8 @@ impl Agent {
                     }
                 }
                 let msg = result
-                    .instructions
-                    .clone()
+                    .instructions()
+                    .map(String::from)
                     .unwrap_or_else(|| "Invalid token. Please try again.".to_string());
                 // Re-emit AuthRequired so web UI re-shows the card
                 let _ = self
@@ -1375,8 +1375,8 @@ impl Agent {
                         StatusUpdate::AuthRequired {
                             extension_name: pending.extension_name.clone(),
                             instructions: Some(msg.clone()),
-                            auth_url: result.auth_url,
-                            setup_url: result.setup_url,
+                            auth_url: result.auth_url().map(String::from),
+                            setup_url: result.setup_url().map(String::from),
                         },
                         &message.metadata,
                     )

src/channels/web/handlers/chat.rs

@@ -142,7 +142,7 @@ pub async fn chat_auth_token_handler(
         .await
         .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
 
-    if result.status == "authenticated" {
+    if result.is_authenticated() {
         // Auto-activate so tools are available immediately
         let msg = match ext_mgr.activate(&req.extension_name).await {
             Ok(r) => format!(
@@ -170,13 +170,14 @@ pub async fn chat_auth_token_handler(
         // Re-emit auth_required for retry
         state.sse.broadcast(SseEvent::AuthRequired {
             extension_name: req.extension_name.clone(),
-            instructions: result.instructions.clone(),
-            auth_url: result.auth_url.clone(),
-            setup_url: result.setup_url.clone(),
+            instructions: result.instructions().map(String::from),
+            auth_url: result.auth_url().map(String::from),
+            setup_url: result.setup_url().map(String::from),
         });
         Ok(Json(ActionResponse::fail(
             result
-                .instructions
+                .instructions()
+                .map(String::from)
                 .unwrap_or_else(|| "Invalid token".to_string()),
         )))
     }

src/channels/web/handlers/extensions.rs

@@ -141,7 +141,7 @@ pub async fn extensions_activate_handler(
 
             // Activation failed due to auth; try authenticating first.
             match ext_mgr.auth(&name, None).await {
-                Ok(auth_result) if auth_result.status == "authenticated" => {
+                Ok(auth_result) if auth_result.is_authenticated() => {
                     // Auth succeeded, retry activation.
                     match ext_mgr.activate(&name).await {
                         Ok(result) => Ok(Json(ActionResponse::ok(result.message))),
@@ -152,13 +152,13 @@ pub async fn extensions_activate_handler(
                     // Auth in progress (OAuth URL or awaiting manual token).
                     let mut resp = ActionResponse::fail(
                         auth_result
-                            .instructions
-                            .clone()
+                            .instructions()
+                            .map(String::from)
                             .unwrap_or_else(|| format!("'{}' requires authentication.", name)),
                     );
-                    resp.auth_url = auth_result.auth_url;
-                    resp.awaiting_token = Some(auth_result.awaiting_token);
-                    resp.instructions = auth_result.instructions;
+                    resp.auth_url = auth_result.auth_url().map(String::from);
+                    resp.awaiting_token = Some(auth_result.is_awaiting_token());
+                    resp.instructions = auth_result.instructions().map(String::from);
                     Ok(Json(resp))
                 }
                 Err(auth_err) => Ok(Json(ActionResponse::fail(format!(

src/channels/web/server.rs

@@ -192,7 +192,9 @@ pub async fn start_server(
             })?;
 
     // Public routes (no auth)
-    let public = Router::new().route("/api/health", get(health_handler));
+    let public = Router::new()
+        .route("/api/health", get(health_handler))
+        .route("/oauth/callback", get(oauth_callback_handler));
 
     // Protected routes (require auth)
     let auth_state = AuthState { token: auth_token };
@@ -424,6 +426,180 @@ async fn health_handler() -> Json<HealthResponse> {
     })
 }
 
+/// Return an OAuth error landing page response.
+fn oauth_error_page(label: &str) -> axum::response::Response {
+    let html = crate::cli::oauth_defaults::landing_html(label, false);
+    axum::response::Html(html).into_response()
+}
+
+/// OAuth callback handler for the web gateway.
+///
+/// This is a PUBLIC route (no Bearer token required) because OAuth providers
+/// redirect the user's browser here. The `state` query parameter correlates
+/// the callback with a pending OAuth flow registered by `start_wasm_oauth()`.
+///
+/// Used on hosted instances where `IRONCLAW_OAUTH_CALLBACK_URL` points to
+/// the gateway (e.g., `https://kind-deer.agent1.near.ai/oauth/callback`).
+/// Local/desktop mode continues to use the TCP listener on port 9876.
+async fn oauth_callback_handler(
+    State(state): State<Arc<GatewayState>>,
+    Query(params): Query<std::collections::HashMap<String, String>>,
+) -> impl IntoResponse {
+    use crate::cli::oauth_defaults;
+
+    // Check for error from OAuth provider (e.g., user denied consent)
+    if let Some(error) = params.get("error") {
+        let description = params
+            .get("error_description")
+            .cloned()
+            .unwrap_or_else(|| error.clone());
+        return oauth_error_page(&description);
+    }
+
+    let state_param = match params.get("state") {
+        Some(s) if !s.is_empty() => s.clone(),
+        _ => return oauth_error_page("IronClaw"),
+    };
+
+    let code = match params.get("code") {
+        Some(c) if !c.is_empty() => c.clone(),
+        _ => return oauth_error_page("IronClaw"),
+    };
+
+    // Look up the pending flow by CSRF state (atomic remove prevents replay)
+    let ext_mgr = match state.extension_manager.as_ref() {
+        Some(mgr) => mgr,
+        None => return oauth_error_page("IronClaw"),
+    };
+
+    // Strip instance prefix from state for registry lookup.
+    // Platform nginx sends `state=instance:nonce` but flows are keyed by nonce only.
+    let lookup_key = oauth_defaults::strip_instance_prefix(&state_param);
+
+    let flow = ext_mgr
+        .pending_oauth_flows()
+        .write()
+        .await
+        .remove(lookup_key);
+
+    let flow = match flow {
+        Some(f) => f,
+        None => {
+            tracing::warn!(
+                state = %state_param,
+                lookup_key = %lookup_key,
+                "OAuth callback received with unknown or expired state"
+            );
+            return oauth_error_page("IronClaw");
+        }
+    };
+
+    // Check flow expiry (5 minutes, matching TCP listener timeout)
+    if flow.created_at.elapsed() > oauth_defaults::OAUTH_FLOW_EXPIRY {
+        tracing::warn!(
+            extension = %flow.extension_name,
+            "OAuth flow expired"
+        );
+        return oauth_error_page(&flow.display_name);
+    }
+
+    // Exchange the authorization code for tokens.
+    // Use the platform exchange proxy when configured (keeps client_secret off container),
+    // otherwise call the provider's token URL directly.
+    let exchange_proxy_url = std::env::var("IRONCLAW_OAUTH_EXCHANGE_URL").ok();
+
+    let result: Result<(), String> = async {
+        let token_response = if let Some(ref proxy_url) = exchange_proxy_url {
+            let gateway_token = flow.gateway_token.as_deref().unwrap_or_default();
+            oauth_defaults::exchange_via_proxy(
+                proxy_url,
+                gateway_token,
+                &code,
+                &flow.redirect_uri,
+                flow.code_verifier.as_deref(),
+                &flow.access_token_field,
+            )
+            .await
+            .map_err(|e| e.to_string())?
+        } else {
+            oauth_defaults::exchange_oauth_code(
+                &flow.token_url,
+                &flow.client_id,
+                flow.client_secret.as_deref(),
+                &code,
+                &flow.redirect_uri,
+                flow.code_verifier.as_deref(),
+                &flow.access_token_field,
+            )
+            .await
+            .map_err(|e| e.to_string())?
+        };
+
+        // Validate the token before storing (catches wrong account, etc.)
+        if let Some(ref validation) = flow.validation_endpoint {
+            oauth_defaults::validate_oauth_token(&token_response.access_token, validation)
+                .await
+                .map_err(|e| e.to_string())?;
+        }
+
+        // Store tokens encrypted in the secrets store
+        oauth_defaults::store_oauth_tokens(
+            flow.secrets.as_ref(),
+            &flow.user_id,
+            &flow.secret_name,
+            flow.provider.as_deref(),
+            &token_response.access_token,
+            token_response.refresh_token.as_deref(),
+            token_response.expires_in,
+            &flow.scopes,
+        )
+        .await
+        .map_err(|e| e.to_string())?;
+
+        Ok(())
+    }
+    .await;
+
+    let (success, message) = match &result {
+        Ok(()) => (
+            true,
+            format!("{} authenticated successfully", flow.display_name),
+        ),
+        Err(e) => (
+            false,
+            format!("{} authentication failed: {}", flow.display_name, e),
+        ),
+    };
+
+    match &result {
+        Ok(()) => {
+            tracing::info!(
+                extension = %flow.extension_name,
+                "OAuth completed successfully via gateway callback"
+            );
+        }
+        Err(e) => {
+            tracing::warn!(
+                extension = %flow.extension_name,
+                error = %e,
+                "OAuth failed via gateway callback"
+            );
+        }
+    }
+
+    // Broadcast SSE event to notify the web UI
+    if let Some(ref sender) = flow.sse_sender {
+        let _ = sender.send(SseEvent::AuthCompleted {
+            extension_name: flow.extension_name,
+            success,
+            message,
+        });
+    }
+
+    let html = oauth_defaults::landing_html(&flow.display_name, success);
+    axum::response::Html(html).into_response()
+}
+
 // --- Chat handlers ---
 
 async fn chat_send_handler(
@@ -552,7 +728,7 @@ async fn chat_auth_token_handler(
         .await
         .map_err(|e| (StatusCode::INTERNAL_SERVER_ERROR, e.to_string()))?;
 
-    if result.status == "authenticated" {
+    if result.is_authenticated() {
         // Auto-activate so tools are available immediately
         let msg = match ext_mgr.activate(&req.extension_name).await {
             Ok(r) => format!(
@@ -580,13 +756,14 @@ async fn chat_auth_token_handler(
         // Re-emit auth_required for retry
         state.sse.broadcast(SseEvent::AuthRequired {
             extension_name: req.extension_name.clone(),
-            instructions: result.instructions.clone(),
-            auth_url: result.auth_url.clone(),
-            setup_url: result.setup_url.clone(),
+            instructions: result.instructions().map(String::from),
+            auth_url: result.auth_url().map(String::from),
+            setup_url: result.setup_url().map(String::from),
         });
         Ok(Json(ActionResponse::fail(
             result
-                .instructions
+                .instructions()
+                .map(String::from)
                 .unwrap_or_else(|| "Invalid token".to_string()),
         )))
     }
@@ -1332,12 +1509,9 @@ async fn extensions_install_handler(
                 // configured (e.g., built-in providers). We only surface an auth_url
                 // when the extension reports it is awaiting authorization.
                 match ext_mgr.auth(&req.name, None).await {
-                    Ok(auth_result)
-                        if auth_result.auth_url.is_some()
-                            && auth_result.status == "awaiting_authorization" =>
-                    {
+                    Ok(auth_result) if auth_result.auth_url().is_some() => {
                         // Scope expansion or initial OAuth: user needs to authorize
-                        resp.auth_url = auth_result.auth_url;
+                        resp.auth_url = auth_result.auth_url().map(String::from);
                     }
                     _ => {}
                 }
@@ -1366,10 +1540,9 @@ async fn extensions_activate_handler(
             // Initial OAuth setup is triggered via save_setup_secrets.
             let mut resp = ActionResponse::ok(result.message);
             if let Ok(auth_result) = ext_mgr.auth(&name, None).await
-                && auth_result.auth_url.is_some()
-                && auth_result.status == "awaiting_authorization"
+                && auth_result.auth_url().is_some()
             {
-                resp.auth_url = auth_result.auth_url;
+                resp.auth_url = auth_result.auth_url().map(String::from);
             }
             Ok(Json(resp))
         }
@@ -1385,7 +1558,7 @@ async fn extensions_activate_handler(
 
             // Activation failed due to auth; try authenticating first.
             match ext_mgr.auth(&name, None).await {
-                Ok(auth_result) if auth_result.status == "authenticated" => {
+                Ok(auth_result) if auth_result.is_authenticated() => {
                     // Auth succeeded, retry activation.
                     match ext_mgr.activate(&name).await {
                         Ok(result) => Ok(Json(ActionResponse::ok(result.message))),
@@ -1396,13 +1569,13 @@ async fn extensions_activate_handler(
                     // Auth in progress (OAuth URL or awaiting manual token).
                     let mut resp = ActionResponse::fail(
                         auth_result
-                            .instructions
-                            .clone()
+                            .instructions()
+                            .map(String::from)
                             .unwrap_or_else(|| format!("'{}' requires authentication.", name)),
                     );
-                    resp.auth_url = auth_result.auth_url;
-                    resp.awaiting_token = Some(auth_result.awaiting_token);
-                    resp.instructions = auth_result.instructions;
+                    resp.auth_url = auth_result.auth_url().map(String::from);
+                    resp.awaiting_token = Some(auth_result.is_awaiting_token());
+                    resp.instructions = auth_result.instructions().map(String::from);
                     Ok(Json(resp))
                 }
                 Err(auth_err) => Ok(Json(ActionResponse::fail(format!(
@@ -2239,4 +2412,343 @@ mod tests {
         let turns = build_turns_from_db_messages(&[]);
         assert!(turns.is_empty());
     }
+
+    // --- OAuth callback handler tests ---
+
+    /// Build a minimal `GatewayState` for testing the OAuth callback handler.
+    fn test_gateway_state(ext_mgr: Option<Arc<ExtensionManager>>) -> Arc<GatewayState> {
+        Arc::new(GatewayState {
+            msg_tx: tokio::sync::RwLock::new(None),
+            sse: SseManager::new(),
+            workspace: None,
+            session_manager: None,
+            log_broadcaster: None,
+            log_level_handle: None,
+            extension_manager: ext_mgr,
+            tool_registry: None,
+            store: None,
+            job_manager: None,
+            prompt_queue: None,
+            user_id: "test".to_string(),
+            shutdown_tx: tokio::sync::RwLock::new(None),
+            ws_tracker: None,
+            llm_provider: None,
+            skill_registry: None,
+            skill_catalog: None,
+            scheduler: None,
+            chat_rate_limiter: RateLimiter::new(30, 60),
+            registry_entries: vec![],
+            cost_guard: None,
+            startup_time: std::time::Instant::now(),
+        })
+    }
+
+    /// Build a test router with just the OAuth callback route.
+    fn test_oauth_router(state: Arc<GatewayState>) -> Router {
+        Router::new()
+            .route("/oauth/callback", get(oauth_callback_handler))
+            .with_state(state)
+    }
+
+    #[tokio::test]
+    async fn test_oauth_callback_missing_params() {
+        use axum::body::Body;
+        use tower::ServiceExt;
+
+        let state = test_gateway_state(None);
+        let app = test_oauth_router(state);
+
+        let req = axum::http::Request::builder()
+            .uri("/oauth/callback")
+            .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"));
+    }
+
+    #[tokio::test]
+    async fn test_oauth_callback_error_from_provider() {
+        use axum::body::Body;
+        use tower::ServiceExt;
+
+        let state = test_gateway_state(None);
+        let app = test_oauth_router(state);
+
+        let req = axum::http::Request::builder()
+            .uri("/oauth/callback?error=access_denied&error_description=access_denied")
+            .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"));
+    }
+
+    #[tokio::test]
+    async fn test_oauth_callback_unknown_state() {
+        use axum::body::Body;
+        use tower::ServiceExt;
+
+        // Build an ExtensionManager so the handler can look up flows
+        let secrets = Arc::new(crate::secrets::InMemorySecretsStore::new(Arc::new(
+            crate::secrets::SecretsCrypto::new(secrecy::SecretString::from(
+                "test-key-at-least-32-chars-long!!".to_string(),
+            ))
+            .expect("crypto"),
+        )));
+        let tool_registry = Arc::new(ToolRegistry::new());
+        let mcp_sm = Arc::new(crate::tools::mcp::session::McpSessionManager::new());
+
+        let ext_mgr = Arc::new(ExtensionManager::new(
+            mcp_sm,
+            secrets,
+            tool_registry,
+            None,
+            None,
+            std::path::PathBuf::from("/tmp/wasm_tools"),
+            std::path::PathBuf::from("/tmp/wasm_channels"),
+            None,
+            "test".to_string(),
+            None,
+            vec![],
+        ));
+
+        let state = test_gateway_state(Some(ext_mgr));
+        let app = test_oauth_router(state);
+
+        let req = axum::http::Request::builder()
+            .uri("/oauth/callback?code=test_code&state=unknown_state_value")
+            .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"));
+    }
+
+    #[tokio::test]
+    async fn test_oauth_callback_expired_flow() {
+        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-key-at-least-32-chars-long!!".to_string(),
+                ))
+                .expect("crypto"),
+            )));
+        let tool_registry = Arc::new(ToolRegistry::new());
+        let mcp_sm = Arc::new(crate::tools::mcp::session::McpSessionManager::new());
+
+        let ext_mgr = Arc::new(ExtensionManager::new(
+            mcp_sm,
+            secrets.clone(),
+            tool_registry,
+            None,
+            None,
+            std::path::PathBuf::from("/tmp/wasm_tools"),
+            std::path::PathBuf::from("/tmp/wasm_channels"),
+            None,
+            "test".to_string(),
+            None,
+            vec![],
+        ));
+
+        // Insert an expired flow (created 10 minutes ago)
+        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_sender: None,
+            gateway_token: None,
+            created_at: std::time::Instant::now() - std::time::Duration::from_secs(600),
+        };
+
+        ext_mgr
+            .pending_oauth_flows()
+            .write()
+            .await
+            .insert("expired_state".to_string(), flow);
+
+        let state = test_gateway_state(Some(ext_mgr));
+        let app = test_oauth_router(state);
+
+        let req = axum::http::Request::builder()
+            .uri("/oauth/callback?code=test_code&state=expired_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);
+        // Expired flow → error landing page
+        assert!(html.contains("Authorization Failed"));
+    }
+
+    #[tokio::test]
+    async fn test_oauth_callback_no_extension_manager() {
+        use axum::body::Body;
+        use tower::ServiceExt;
+
+        // No extension manager set → graceful error
+        let state = test_gateway_state(None);
+        let app = test_oauth_router(state);
+
+        let req = axum::http::Request::builder()
+            .uri("/oauth/callback?code=test_code&state=some_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"));
+    }
+
+    #[tokio::test]
+    async fn test_oauth_callback_strips_instance_prefix() {
+        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-key-at-least-32-chars-long!!".to_string(),
+                ))
+                .expect("crypto"),
+            )));
+        let tool_registry = Arc::new(ToolRegistry::new());
+        let mcp_sm = Arc::new(crate::tools::mcp::session::McpSessionManager::new());
+
+        let ext_mgr = Arc::new(ExtensionManager::new(
+            mcp_sm,
+            secrets.clone(),
+            tool_registry,
+            None,
+            None,
+            std::path::PathBuf::from("/tmp/wasm_tools"),
+            std::path::PathBuf::from("/tmp/wasm_channels"),
+            None,
+            "test".to_string(),
+            None,
+            vec![],
+        ));
+
+        // Insert a flow keyed by raw nonce "test_nonce" (without instance prefix).
+        // Use an expired flow so the handler exits before attempting a real HTTP
+        // token exchange — we only need to verify that the instance prefix was
+        // stripped and the flow was found by the raw nonce.
+        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_sender: None,
+            gateway_token: None,
+            // Expired — handler will reject after lookup (no network I/O)
+            created_at: std::time::Instant::now() - std::time::Duration::from_secs(600),
+        };
+
+        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);
+
+        // Send callback with instance prefix: "myinstance:test_nonce"
+        // The handler should strip "myinstance:" and find the flow keyed by "test_nonce"
+        let req = axum::http::Request::builder()
+            .uri("/oauth/callback?code=fake_code&state=myinstance:test_nonce")
+            .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);
+
+        // The flow was found (stripped prefix matched) but is expired, so the
+        // handler returns an error landing page. The flow being consumed from
+        // the registry (checked below) proves the prefix was stripped correctly.
+        assert!(
+            html.contains("Authorization Failed"),
+            "Expected error page, html was: {}",
+            &html[..html.len().min(500)]
+        );
+
+        // Verify the flow was consumed (removed from registry)
+        assert!(
+            ext_mgr
+                .pending_oauth_flows()
+                .read()
+                .await
+                .get("test_nonce")
+                .is_none()
+        );
+    }
 }

src/channels/web/static/app.js

@@ -2013,7 +2013,11 @@ function renderExtensionCard(ext) {
       actions.appendChild(activateBtn);
     }
 
-    if (ext.needs_setup || ext.has_auth) {
+    // Show Configure/Reconfigure button when there are secrets to enter.
+    // 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.needs_setup || (ext.has_auth && ext.authenticated)) {
       const configBtn = document.createElement('button');
       configBtn.className = 'btn-ext configure';
       configBtn.textContent = ext.authenticated ? 'Reconfigure' : 'Configure';

src/channels/web/ws.rs

@@ -242,7 +242,7 @@ async fn handle_client_message(
         } => {
             if let Some(ref ext_mgr) = state.extension_manager {
                 match ext_mgr.auth(&extension_name, Some(&token)).await {
-                    Ok(result) if result.status == "authenticated" => {
+                    Ok(result) if result.is_authenticated() => {
                         let msg = match ext_mgr.activate(&extension_name).await {
                             Ok(r) => format!(
                                 "{} authenticated ({} tools loaded)",
@@ -268,9 +268,9 @@ async fn handle_client_message(
                             .sse
                             .broadcast(crate::channels::web::types::SseEvent::AuthRequired {
                                 extension_name,
-                                instructions: result.instructions,
-                                auth_url: result.auth_url,
-                                setup_url: result.setup_url,
+                                instructions: result.instructions().map(String::from),
+                                auth_url: result.auth_url().map(String::from),
+                                setup_url: result.setup_url().map(String::from),
                             });
                     }
                     Err(e) => {

src/cli/oauth_defaults.rs

@@ -18,6 +18,7 @@
 //!   env vars, which take priority over built-in defaults.
 
 use std::collections::HashMap;
+use std::sync::Arc;
 use std::time::Duration;
 
 use base64::{Engine, engine::general_purpose::URL_SAFE_NO_PAD};
@@ -25,6 +26,7 @@ use rand::RngCore;
 use sha2::{Digest, Sha256};
 use tokio::io::{AsyncBufReadExt, AsyncWriteExt, BufReader};
 use tokio::net::TcpListener;
+use tokio::sync::RwLock;
 
 use crate::secrets::{CreateSecretParams, SecretsStore};
 
@@ -683,6 +685,219 @@ pub fn landing_html(provider_name: &str, success: bool) -> String {
     )
 }
 
+// ── Gateway callback support ─────────────────────────────────────────
+
+/// State for an in-progress OAuth flow, keyed by CSRF `state` parameter.
+///
+/// Created by `start_wasm_oauth()` and consumed by the web gateway's
+/// `/oauth/callback` handler when running in hosted mode.
+pub struct PendingOAuthFlow {
+    /// Extension name (e.g., "google_calendar").
+    pub extension_name: String,
+    /// Human-readable display name (e.g., "Google Calendar").
+    pub display_name: String,
+    /// OAuth token exchange URL.
+    pub token_url: String,
+    /// OAuth client ID.
+    pub client_id: String,
+    /// OAuth client secret (optional for PKCE-only flows).
+    pub client_secret: Option<String>,
+    /// The redirect_uri used in the authorization request.
+    pub redirect_uri: String,
+    /// PKCE code verifier (must match the code_challenge sent in the auth URL).
+    pub code_verifier: Option<String>,
+    /// Field name in token response containing the access token.
+    pub access_token_field: String,
+    /// Secret name for storage (e.g., "google_oauth_token").
+    pub secret_name: String,
+    /// Provider hint (e.g., "google").
+    pub provider: Option<String>,
+    /// Token validation endpoint (optional).
+    pub validation_endpoint: Option<crate::tools::wasm::ValidationEndpointSchema>,
+    /// Scopes that were requested.
+    pub scopes: Vec<String>,
+    /// User ID for secret storage.
+    pub user_id: String,
+    /// Secrets store reference for token persistence.
+    pub secrets: Arc<dyn SecretsStore + Send + Sync>,
+    /// SSE broadcast sender for notifying the web UI.
+    pub sse_sender: Option<tokio::sync::broadcast::Sender<crate::channels::web::types::SseEvent>>,
+    /// Gateway auth token for authenticating with the platform token exchange proxy.
+    pub gateway_token: Option<String>,
+    /// When this flow was created (for expiry).
+    pub created_at: std::time::Instant,
+}
+
+impl std::fmt::Debug for PendingOAuthFlow {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        f.debug_struct("PendingOAuthFlow")
+            .field("extension_name", &self.extension_name)
+            .field("display_name", &self.display_name)
+            .field("secret_name", &self.secret_name)
+            .field("created_at", &self.created_at)
+            .finish_non_exhaustive()
+    }
+}
+
+/// Thread-safe registry of pending OAuth flows, keyed by CSRF `state` parameter.
+pub type PendingOAuthRegistry = Arc<RwLock<HashMap<String, PendingOAuthFlow>>>;
+
+/// Create a new empty pending OAuth flow registry.
+pub fn new_pending_oauth_registry() -> PendingOAuthRegistry {
+    Arc::new(RwLock::new(HashMap::new()))
+}
+
+/// Returns `true` if OAuth callbacks should be routed through the web gateway
+/// instead of the local TCP listener.
+///
+/// This is the case when `IRONCLAW_OAUTH_CALLBACK_URL` is set to a non-loopback
+/// URL, meaning the user's browser will redirect to a hosted gateway rather than
+/// localhost.
+pub fn use_gateway_callback() -> bool {
+    std::env::var("IRONCLAW_OAUTH_CALLBACK_URL")
+        .ok()
+        .filter(|v| !v.is_empty())
+        .map(|raw| {
+            url::Url::parse(&raw)
+                .ok()
+                .and_then(|u| u.host_str().map(String::from))
+                .map(|host| !is_loopback_host(&host))
+                .unwrap_or(false)
+        })
+        .unwrap_or(false)
+}
+
+/// Maximum age for pending OAuth flows (5 minutes, matching TCP listener timeout).
+pub const OAUTH_FLOW_EXPIRY: Duration = Duration::from_secs(300);
+
+/// Remove expired flows from the registry.
+///
+/// Called when inserting new flows to prevent accumulation from abandoned
+/// OAuth attempts.
+pub async fn sweep_expired_flows(registry: &PendingOAuthRegistry) {
+    let mut flows = registry.write().await;
+    flows.retain(|_, flow| flow.created_at.elapsed() < OAUTH_FLOW_EXPIRY);
+}
+
+// ── Platform routing helpers ────────────────────────────────────────
+
+/// Prepend instance name to CSRF state for platform routing.
+///
+/// The NEAR AI platform nginx proxy at `auth.DOMAIN` parses the instance name
+/// from the `state` query parameter (format: `instance:nonce`) to route the
+/// OAuth callback to the correct container.
+///
+/// Returns the nonce unchanged when `IRONCLAW_INSTANCE_NAME` is not set
+/// (local/non-platform mode).
+pub fn build_platform_state(nonce: &str) -> String {
+    let instance = std::env::var("IRONCLAW_INSTANCE_NAME")
+        .or_else(|_| std::env::var("OPENCLAW_INSTANCE_NAME"))
+        .ok()
+        .filter(|v| !v.is_empty());
+    match instance {
+        Some(name) => format!("{}:{}", name, nonce),
+        None => nonce.to_string(),
+    }
+}
+
+/// Strip the instance prefix from a state parameter to recover the lookup nonce.
+///
+/// `"myinstance:abc123"` → `"abc123"`, `"abc123"` → `"abc123"` (no prefix).
+///
+/// Safe because nonces are base64url-encoded (`[A-Za-z0-9_-]`, no colons).
+pub fn strip_instance_prefix(state: &str) -> &str {
+    state
+        .split_once(':')
+        .map(|(_, nonce)| nonce)
+        .unwrap_or(state)
+}
+
+/// Exchange an OAuth authorization code via the platform's token exchange proxy.
+///
+/// The proxy holds `client_secret` server-side so the container never sees it.
+/// Authenticated via the gateway auth token (Bearer header).
+///
+/// The proxy expects form params `{code, redirect_uri, code_verifier}` and
+/// returns a standard Google token response `{access_token, refresh_token, expires_in}`.
+pub async fn exchange_via_proxy(
+    proxy_url: &str,
+    gateway_token: &str,
+    code: &str,
+    redirect_uri: &str,
+    code_verifier: Option<&str>,
+    access_token_field: &str,
+) -> Result<OAuthTokenResponse, OAuthCallbackError> {
+    if gateway_token.is_empty() {
+        return Err(OAuthCallbackError::Io(
+            "Gateway auth token is required for proxy token exchange".to_string(),
+        ));
+    }
+    let exchange_url = format!("{}/oauth/exchange", proxy_url.trim_end_matches('/'));
+
+    let client = reqwest::Client::builder()
+        .timeout(Duration::from_secs(60))
+        .build()
+        .map_err(|e| OAuthCallbackError::Io(format!("Failed to build HTTP client: {}", e)))?;
+    let mut params = vec![
+        ("code", code.to_string()),
+        ("redirect_uri", redirect_uri.to_string()),
+    ];
+    if let Some(verifier) = code_verifier {
+        params.push(("code_verifier", verifier.to_string()));
+    }
+
+    let response = client
+        .post(&exchange_url)
+        .bearer_auth(gateway_token)
+        .form(&params)
+        .send()
+        .await
+        .map_err(|e| {
+            OAuthCallbackError::Io(format!("Token exchange proxy request failed: {}", e))
+        })?;
+
+    if !response.status().is_success() {
+        let status = response.status();
+        let body = response.text().await.unwrap_or_default();
+        return Err(OAuthCallbackError::Io(format!(
+            "Token exchange proxy failed: {} - {}",
+            status, body
+        )));
+    }
+
+    let token_data: serde_json::Value = response
+        .json()
+        .await
+        .map_err(|e| OAuthCallbackError::Io(format!("Failed to parse proxy response: {}", e)))?;
+
+    let access_token = token_data
+        .get(access_token_field)
+        .and_then(|v| v.as_str())
+        .ok_or_else(|| {
+            let fields: Vec<&str> = token_data
+                .as_object()
+                .map(|o| o.keys().map(|k| k.as_str()).collect())
+                .unwrap_or_default();
+            OAuthCallbackError::Io(format!(
+                "No '{}' field in proxy response (fields present: {:?})",
+                access_token_field, fields
+            ))
+        })?
+        .to_string();
+
+    let refresh_token = token_data
+        .get("refresh_token")
+        .and_then(|v| v.as_str())
+        .map(String::from);
+    let expires_in = token_data.get("expires_in").and_then(|v| v.as_u64());
+
+    Ok(OAuthTokenResponse {
+        access_token,
+        refresh_token,
+        expires_in,
+    })
+}
+
 #[cfg(test)]
 mod tests {
     use std::sync::Mutex;
@@ -939,4 +1154,161 @@ mod tests {
         // State should be different each time (random)
         assert_ne!(result1.state, result2.state);
     }
+
+    #[test]
+    fn test_use_gateway_callback_false_by_default() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        let original = std::env::var("IRONCLAW_OAUTH_CALLBACK_URL").ok();
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe {
+            std::env::remove_var("IRONCLAW_OAUTH_CALLBACK_URL");
+        }
+        assert!(!crate::cli::oauth_defaults::use_gateway_callback());
+        unsafe {
+            if let Some(val) = original {
+                std::env::set_var("IRONCLAW_OAUTH_CALLBACK_URL", val);
+            }
+        }
+    }
+
+    #[test]
+    fn test_use_gateway_callback_true_for_hosted() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        let original = std::env::var("IRONCLAW_OAUTH_CALLBACK_URL").ok();
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe {
+            std::env::set_var(
+                "IRONCLAW_OAUTH_CALLBACK_URL",
+                "https://kind-deer.agent1.near.ai",
+            );
+        }
+        assert!(crate::cli::oauth_defaults::use_gateway_callback());
+        unsafe {
+            if let Some(val) = original {
+                std::env::set_var("IRONCLAW_OAUTH_CALLBACK_URL", val);
+            } else {
+                std::env::remove_var("IRONCLAW_OAUTH_CALLBACK_URL");
+            }
+        }
+    }
+
+    #[test]
+    fn test_use_gateway_callback_false_for_localhost() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        let original = std::env::var("IRONCLAW_OAUTH_CALLBACK_URL").ok();
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe {
+            std::env::set_var("IRONCLAW_OAUTH_CALLBACK_URL", "http://127.0.0.1:3001");
+        }
+        assert!(!crate::cli::oauth_defaults::use_gateway_callback());
+        unsafe {
+            if let Some(val) = original {
+                std::env::set_var("IRONCLAW_OAUTH_CALLBACK_URL", val);
+            } else {
+                std::env::remove_var("IRONCLAW_OAUTH_CALLBACK_URL");
+            }
+        }
+    }
+
+    #[test]
+    fn test_use_gateway_callback_false_for_empty() {
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        let original = std::env::var("IRONCLAW_OAUTH_CALLBACK_URL").ok();
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe {
+            std::env::set_var("IRONCLAW_OAUTH_CALLBACK_URL", "");
+        }
+        assert!(!crate::cli::oauth_defaults::use_gateway_callback());
+        unsafe {
+            if let Some(val) = original {
+                std::env::set_var("IRONCLAW_OAUTH_CALLBACK_URL", val);
+            } else {
+                std::env::remove_var("IRONCLAW_OAUTH_CALLBACK_URL");
+            }
+        }
+    }
+
+    #[test]
+    fn test_build_platform_state_with_instance() {
+        use crate::cli::oauth_defaults::build_platform_state;
+
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        let original = std::env::var("IRONCLAW_INSTANCE_NAME").ok();
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe {
+            std::env::set_var("IRONCLAW_INSTANCE_NAME", "kind-deer");
+        }
+        assert_eq!(build_platform_state("abc123"), "kind-deer:abc123");
+        unsafe {
+            if let Some(val) = original {
+                std::env::set_var("IRONCLAW_INSTANCE_NAME", val);
+            } else {
+                std::env::remove_var("IRONCLAW_INSTANCE_NAME");
+            }
+        }
+    }
+
+    #[test]
+    fn test_build_platform_state_without_instance() {
+        use crate::cli::oauth_defaults::build_platform_state;
+
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        let original = std::env::var("IRONCLAW_INSTANCE_NAME").ok();
+        let original_oc = std::env::var("OPENCLAW_INSTANCE_NAME").ok();
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe {
+            std::env::remove_var("IRONCLAW_INSTANCE_NAME");
+            std::env::remove_var("OPENCLAW_INSTANCE_NAME");
+        }
+        assert_eq!(build_platform_state("abc123"), "abc123");
+        unsafe {
+            if let Some(val) = original {
+                std::env::set_var("IRONCLAW_INSTANCE_NAME", val);
+            }
+            if let Some(val) = original_oc {
+                std::env::set_var("OPENCLAW_INSTANCE_NAME", val);
+            }
+        }
+    }
+
+    #[test]
+    fn test_build_platform_state_with_openclaw_instance() {
+        use crate::cli::oauth_defaults::build_platform_state;
+
+        let _guard = ENV_MUTEX.lock().expect("env mutex poisoned");
+        let original_ic = std::env::var("IRONCLAW_INSTANCE_NAME").ok();
+        let original_oc = std::env::var("OPENCLAW_INSTANCE_NAME").ok();
+        // SAFETY: Under ENV_MUTEX, no concurrent env access.
+        unsafe {
+            std::env::remove_var("IRONCLAW_INSTANCE_NAME");
+            std::env::set_var("OPENCLAW_INSTANCE_NAME", "quiet-lion");
+        }
+        assert_eq!(build_platform_state("xyz789"), "quiet-lion:xyz789");
+        unsafe {
+            if let Some(val) = original_ic {
+                std::env::set_var("IRONCLAW_INSTANCE_NAME", val);
+            }
+            if let Some(val) = original_oc {
+                std::env::set_var("OPENCLAW_INSTANCE_NAME", val);
+            } else {
+                std::env::remove_var("OPENCLAW_INSTANCE_NAME");
+            }
+        }
+    }
+
+    #[test]
+    fn test_strip_instance_prefix_with_colon() {
+        use crate::cli::oauth_defaults::strip_instance_prefix;
+
+        assert_eq!(strip_instance_prefix("kind-deer:abc123"), "abc123");
+        assert_eq!(strip_instance_prefix("my-instance:xyz"), "xyz");
+    }
+
+    #[test]
+    fn test_strip_instance_prefix_without_colon() {
+        use crate::cli::oauth_defaults::strip_instance_prefix;
+
+        assert_eq!(strip_instance_prefix("abc123"), "abc123");
+        assert_eq!(strip_instance_prefix(""), "");
+    }
 }

src/extensions/mod.rs

@@ -24,6 +24,7 @@ pub use discovery::OnlineDiscovery;
 pub use manager::ExtensionManager;
 pub use registry::ExtensionRegistry;
 
+use serde::ser::SerializeMap;
 use serde::{Deserialize, Serialize};
 
 /// The kind of extension, determining how it's installed, authenticated, and activated.
@@ -145,28 +146,267 @@ pub struct InstallResult {
     pub message: String,
 }
 
+/// Auth readiness state for the extensions list UI.
+///
+/// Used by `check_tool_auth_status` and `check_channel_auth_status` to
+/// communicate a tool's credential state to the list handler without
+/// ambiguous `(bool, bool)` tuples.
+#[derive(Debug, Clone, Copy, PartialEq, Eq)]
+pub enum ToolAuthState {
+    /// Token/credentials are present — ready to use.
+    Ready,
+    /// Auth section exists but the access token is missing (OAuth not completed).
+    NeedsAuth,
+    /// Setup credentials (client_id/secret) must be configured before OAuth can start.
+    NeedsSetup,
+    /// No auth configuration at all (no capabilities or auth section).
+    NoAuth,
+}
+
+/// The typed auth status, carrying only the data relevant to each state.
+#[derive(Debug, Clone, PartialEq, Eq)]
+pub enum AuthStatus {
+    /// Authentication is complete; no further action needed.
+    Authenticated,
+    /// No authentication is required for this extension.
+    NoAuthRequired,
+    /// OAuth flow started — user must open `auth_url` in their browser.
+    AwaitingAuthorization {
+        auth_url: String,
+        callback_type: String,
+    },
+    /// Waiting for user to provide a token/key manually.
+    AwaitingToken {
+        instructions: String,
+        setup_url: Option<String>,
+    },
+    /// OAuth client credentials need to be configured before auth can proceed.
+    NeedsSetup {
+        instructions: String,
+        setup_url: Option<String>,
+    },
+}
+
+impl AuthStatus {
+    /// The wire-format status string (backward-compatible with JS consumers).
+    pub fn as_str(&self) -> &'static str {
+        match self {
+            AuthStatus::Authenticated => "authenticated",
+            AuthStatus::NoAuthRequired => "no_auth_required",
+            AuthStatus::AwaitingAuthorization { .. } => "awaiting_authorization",
+            AuthStatus::AwaitingToken { .. } => "awaiting_token",
+            AuthStatus::NeedsSetup { .. } => "needs_setup",
+        }
+    }
+}
+
 /// Result of authenticating an extension.
-#[derive(Debug, Clone, Serialize, Deserialize)]
+#[derive(Debug, Clone)]
 pub struct AuthResult {
     pub name: String,
     pub kind: ExtensionKind,
-    /// OAuth URL to open (for OAuth flows).
-    #[serde(skip_serializing_if = "Option::is_none")]
-    pub auth_url: Option<String>,
-    /// Whether using local or remote callback.
-    #[serde(skip_serializing_if = "Option::is_none")]
-    pub callback_type: Option<String>,
-    /// Instructions for manual token entry (for WASM tools).
-    #[serde(skip_serializing_if = "Option::is_none")]
-    pub instructions: Option<String>,
-    /// URL for manual token setup.
-    #[serde(skip_serializing_if = "Option::is_none")]
-    pub setup_url: Option<String>,
-    /// Whether the tool is waiting for a token from the user.
-    #[serde(default)]
-    pub awaiting_token: bool,
-    /// Current auth status.
-    pub status: String,
+    pub status: AuthStatus,
+}
+
+impl AuthResult {
+    // ── Constructors ──────────────────────────────────────────────────
+
+    pub fn authenticated(name: impl Into<String>, kind: ExtensionKind) -> Self {
+        Self {
+            name: name.into(),
+            kind,
+            status: AuthStatus::Authenticated,
+        }
+    }
+
+    pub fn no_auth_required(name: impl Into<String>, kind: ExtensionKind) -> Self {
+        Self {
+            name: name.into(),
+            kind,
+            status: AuthStatus::NoAuthRequired,
+        }
+    }
+
+    pub fn awaiting_authorization(
+        name: impl Into<String>,
+        kind: ExtensionKind,
+        auth_url: String,
+        callback_type: String,
+    ) -> Self {
+        Self {
+            name: name.into(),
+            kind,
+            status: AuthStatus::AwaitingAuthorization {
+                auth_url,
+                callback_type,
+            },
+        }
+    }
+
+    pub fn awaiting_token(
+        name: impl Into<String>,
+        kind: ExtensionKind,
+        instructions: String,
+        setup_url: Option<String>,
+    ) -> Self {
+        Self {
+            name: name.into(),
+            kind,
+            status: AuthStatus::AwaitingToken {
+                instructions,
+                setup_url,
+            },
+        }
+    }
+
+    pub fn needs_setup(
+        name: impl Into<String>,
+        kind: ExtensionKind,
+        instructions: String,
+        setup_url: Option<String>,
+    ) -> Self {
+        Self {
+            name: name.into(),
+            kind,
+            status: AuthStatus::NeedsSetup {
+                instructions,
+                setup_url,
+            },
+        }
+    }
+
+    // ── Accessors ─────────────────────────────────────────────────────
+
+    pub fn is_authenticated(&self) -> bool {
+        matches!(self.status, AuthStatus::Authenticated)
+    }
+
+    pub fn auth_url(&self) -> Option<&str> {
+        match &self.status {
+            AuthStatus::AwaitingAuthorization { auth_url, .. } => Some(auth_url),
+            _ => None,
+        }
+    }
+
+    pub fn callback_type(&self) -> Option<&str> {
+        match &self.status {
+            AuthStatus::AwaitingAuthorization { callback_type, .. } => Some(callback_type),
+            _ => None,
+        }
+    }
+
+    pub fn instructions(&self) -> Option<&str> {
+        match &self.status {
+            AuthStatus::AwaitingToken { instructions, .. }
+            | AuthStatus::NeedsSetup { instructions, .. } => Some(instructions),
+            _ => None,
+        }
+    }
+
+    pub fn setup_url(&self) -> Option<&str> {
+        match &self.status {
+            AuthStatus::AwaitingToken { setup_url, .. }
+            | AuthStatus::NeedsSetup { setup_url, .. } => setup_url.as_deref(),
+            _ => None,
+        }
+    }
+
+    pub fn is_awaiting_token(&self) -> bool {
+        matches!(self.status, AuthStatus::AwaitingToken { .. })
+    }
+
+    pub fn status_str(&self) -> &'static str {
+        self.status.as_str()
+    }
+}
+
+/// Serialize `AuthResult` to the same flat JSON shape the JS frontend expects.
+impl Serialize for AuthResult {
+    fn serialize<S: serde::Serializer>(&self, serializer: S) -> Result<S::Ok, S::Error> {
+        // Count fields: name + kind + status + optional fields
+        let optional_count = self.auth_url().is_some() as usize
+            + self.callback_type().is_some() as usize
+            + self.instructions().is_some() as usize
+            + self.setup_url().is_some() as usize;
+        let mut map = serializer.serialize_map(Some(4 + optional_count))?;
+
+        map.serialize_entry("name", &self.name)?;
+        map.serialize_entry("kind", &self.kind)?;
+        if let Some(url) = self.auth_url() {
+            map.serialize_entry("auth_url", url)?;
+        }
+        if let Some(cb) = self.callback_type() {
+            map.serialize_entry("callback_type", cb)?;
+        }
+        if let Some(inst) = self.instructions() {
+            map.serialize_entry("instructions", inst)?;
+        }
+        if let Some(url) = self.setup_url() {
+            map.serialize_entry("setup_url", url)?;
+        }
+        map.serialize_entry("awaiting_token", &self.is_awaiting_token())?;
+        map.serialize_entry("status", self.status_str())?;
+        map.end()
+    }
+}
+
+/// Deserialize from the flat JSON shape back into the typed enum.
+impl<'de> Deserialize<'de> for AuthResult {
+    fn deserialize<D: serde::Deserializer<'de>>(deserializer: D) -> Result<Self, D::Error> {
+        /// Flat helper matching the old JSON shape.
+        #[derive(Deserialize)]
+        #[allow(dead_code)]
+        struct Raw {
+            name: String,
+            kind: ExtensionKind,
+            #[serde(default)]
+            auth_url: Option<String>,
+            #[serde(default)]
+            callback_type: Option<String>,
+            #[serde(default)]
+            instructions: Option<String>,
+            #[serde(default)]
+            setup_url: Option<String>,
+            #[serde(default)]
+            awaiting_token: bool,
+            status: String,
+        }
+
+        let raw = Raw::deserialize(deserializer)?;
+        let status = match raw.status.as_str() {
+            "authenticated" => AuthStatus::Authenticated,
+            "no_auth_required" => AuthStatus::NoAuthRequired,
+            "awaiting_authorization" => AuthStatus::AwaitingAuthorization {
+                auth_url: raw.auth_url.unwrap_or_default(),
+                callback_type: raw.callback_type.unwrap_or_default(),
+            },
+            "awaiting_token" => AuthStatus::AwaitingToken {
+                instructions: raw.instructions.unwrap_or_default(),
+                setup_url: raw.setup_url,
+            },
+            "needs_setup" => AuthStatus::NeedsSetup {
+                instructions: raw.instructions.unwrap_or_default(),
+                setup_url: raw.setup_url,
+            },
+            other => {
+                return Err(serde::de::Error::unknown_variant(
+                    other,
+                    &[
+                        "authenticated",
+                        "no_auth_required",
+                        "awaiting_authorization",
+                        "awaiting_token",
+                        "needs_setup",
+                    ],
+                ));
+            }
+        };
+        Ok(AuthResult {
+            name: raw.name,
+            kind: raw.kind,
+            status,
+        })
+    }
 }
 
 /// Result of activating an extension.
@@ -257,3 +497,124 @@ pub enum ExtensionError {
     #[error("{0}")]
     Other(String),
 }
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn auth_result_authenticated_round_trip() {
+        let result = AuthResult::authenticated("gmail", ExtensionKind::WasmTool);
+        let json = serde_json::to_value(&result).unwrap();
+
+        assert_eq!(json["status"], "authenticated");
+        assert_eq!(json["name"], "gmail");
+        assert_eq!(json["kind"], "wasm_tool");
+        assert_eq!(json["awaiting_token"], false);
+        assert!(json.get("auth_url").is_none());
+        assert!(json.get("instructions").is_none());
+
+        let back: AuthResult = serde_json::from_value(json).unwrap();
+        assert!(back.is_authenticated());
+        assert!(back.auth_url().is_none());
+    }
+
+    #[test]
+    fn auth_result_awaiting_authorization_round_trip() {
+        let result = AuthResult::awaiting_authorization(
+            "google-drive",
+            ExtensionKind::WasmTool,
+            "https://accounts.google.com/o/oauth2/v2/auth?state=abc".to_string(),
+            "local".to_string(),
+        );
+        let json = serde_json::to_value(&result).unwrap();
+
+        assert_eq!(json["status"], "awaiting_authorization");
+        assert_eq!(
+            json["auth_url"],
+            "https://accounts.google.com/o/oauth2/v2/auth?state=abc"
+        );
+        assert_eq!(json["callback_type"], "local");
+        assert_eq!(json["awaiting_token"], false);
+
+        let back: AuthResult = serde_json::from_value(json).unwrap();
+        assert_eq!(
+            back.auth_url(),
+            Some("https://accounts.google.com/o/oauth2/v2/auth?state=abc")
+        );
+        assert_eq!(back.callback_type(), Some("local"));
+        assert!(!back.is_authenticated());
+    }
+
+    #[test]
+    fn auth_result_awaiting_token_round_trip() {
+        let result = AuthResult::awaiting_token(
+            "telegram",
+            ExtensionKind::WasmChannel,
+            "Enter your bot token".to_string(),
+            None,
+        );
+        let json = serde_json::to_value(&result).unwrap();
+
+        assert_eq!(json["status"], "awaiting_token");
+        assert_eq!(json["instructions"], "Enter your bot token");
+        assert_eq!(json["awaiting_token"], true);
+        assert!(json.get("auth_url").is_none());
+
+        let back: AuthResult = serde_json::from_value(json).unwrap();
+        assert!(back.is_awaiting_token());
+        assert_eq!(back.instructions(), Some("Enter your bot token"));
+    }
+
+    #[test]
+    fn auth_result_needs_setup_round_trip() {
+        let result = AuthResult::needs_setup(
+            "custom-tool",
+            ExtensionKind::WasmTool,
+            "Configure OAuth credentials in the Setup tab.".to_string(),
+            Some("https://console.cloud.google.com".to_string()),
+        );
+        let json = serde_json::to_value(&result).unwrap();
+
+        assert_eq!(json["status"], "needs_setup");
+        assert_eq!(json["setup_url"], "https://console.cloud.google.com");
+        assert_eq!(json["awaiting_token"], false);
+
+        let back: AuthResult = serde_json::from_value(json).unwrap();
+        assert!(!back.is_authenticated());
+        assert!(!back.is_awaiting_token());
+        assert_eq!(back.setup_url(), Some("https://console.cloud.google.com"));
+    }
+
+    #[test]
+    fn auth_result_no_auth_required_round_trip() {
+        let result = AuthResult::no_auth_required("echo", ExtensionKind::WasmTool);
+        let json = serde_json::to_value(&result).unwrap();
+
+        assert_eq!(json["status"], "no_auth_required");
+        assert_eq!(json["awaiting_token"], false);
+
+        let back: AuthResult = serde_json::from_value(json).unwrap();
+        assert!(!back.is_authenticated());
+        assert_eq!(back.status, AuthStatus::NoAuthRequired);
+    }
+
+    #[test]
+    fn auth_status_type_safety() {
+        // AwaitingAuthorization always has auth_url
+        let result = AuthResult::awaiting_authorization(
+            "test",
+            ExtensionKind::WasmTool,
+            "https://example.com".to_string(),
+            "local".to_string(),
+        );
+        assert!(result.auth_url().is_some());
+        assert!(!result.is_awaiting_token());
+
+        // Authenticated never has auth_url
+        let result = AuthResult::authenticated("test", ExtensionKind::WasmTool);
+        assert!(result.auth_url().is_none());
+        assert!(result.instructions().is_none());
+        assert!(result.setup_url().is_none());
+    }
+}

src/tools/builtin/extension_tools.rs

@@ -218,7 +218,7 @@ impl Tool for ToolAuthTool {
             .map_err(|e| ToolError::ExecutionFailed(e.to_string()))?;
 
         // Auto-activate after successful auth so tools are available immediately
-        if result.status == "authenticated" {
+        if result.is_authenticated() {
             match self.manager.activate(name).await {
                 Ok(activate_result) => {
                     let output = serde_json::json!({
@@ -324,7 +324,7 @@ impl Tool for ToolActivateTool {
                 // Activation failed due to missing auth; initiate auth flow
                 // so the agent loop can show the auth card.
                 match self.manager.auth(name, None).await {
-                    Ok(auth_result) if auth_result.status == "authenticated" => {
+                    Ok(auth_result) if auth_result.is_authenticated() => {
                         // Auth succeeded (e.g. env var was set); retry activation.
                         let result = self
                             .manager

src/tools/wasm/wrapper.rs

@@ -656,10 +656,17 @@ impl Tool for WasmToolWrapper {
         // Pre-resolve host credentials from secrets store (async, before blocking task).
         // This decrypts the secrets once so the sync http_request() host function
         // can inject them without needing async access.
+        //
+        // BUG FIX: ExtensionManager stores OAuth tokens under user_id "default"
+        // (hardcoded at construction in app.rs), but this was previously looking
+        // them up under ctx.user_id — which could be a Telegram user ID, web
+        // gateway user, etc. — causing credential resolution to silently fail.
+        // Must match the storage key until per-user credential isolation is added.
+        let credential_user_id = "default";
         let host_credentials = resolve_host_credentials(
             &self.capabilities,
             self.secrets_store.as_deref(),
-            &ctx.user_id,
+            credential_user_id,
             self.oauth_refresh.as_ref(),
         )
         .await;