diff --git a/FEATURE_PARITY.md b/FEATURE_PARITY.md
index d00ff5e5df..85348de539 100644
--- a/FEATURE_PARITY.md
+++ b/FEATURE_PARITY.md
@@ -68,7 +68,7 @@ This document tracks feature parity between IronClaw (Rust implementation) and O
 | REPL (simple) | ✅ | ✅ | - | For testing |
 | WASM channels | ❌ | ✅ | - | IronClaw innovation; host resolves owner scope vs sender identity |
 | WhatsApp | ✅ | ❌ | P1 | Baileys (Web), same-phone mode with echo detection |
-| Telegram | ✅ | ✅ | - | WASM channel(MTProto), DM pairing, caption, /start, bot_username, DM topics, setup-time owner verification, owner-scoped persistence |
+| Telegram | ✅ | ✅ | - | WASM channel(MTProto), DM pairing, caption, /start, bot_username, DM topics, setup-time owner auto-verification, owner-scoped persistence |
 | Discord | ✅ | ❌ | P2 | discord.js, thread parent binding inheritance |
 | Signal | ✅ | ✅ | P2 | signal-cli daemonPC, SSE listener HTTP/JSON-R, user/group allowlists, DM pairing |
 | Slack | ✅ | ✅ | - | WASM tool |
diff --git a/src/agent/agent_loop.rs b/src/agent/agent_loop.rs
index aaaad879d1..83d971ef1a 100644
--- a/src/agent/agent_loop.rs
+++ b/src/agent/agent_loop.rs
@@ -54,16 +54,65 @@ pub(crate) fn truncate_for_preview(output: &str, max_chars: usize) -> String {
     }
 }
 
+#[cfg(test)]
 fn resolve_routine_notification_user(metadata: &serde_json::Value) -> Option<String> {
-    metadata
-        .get("notify_user")
-        .and_then(|value| value.as_str())
-        .or_else(|| metadata.get("owner_id").and_then(|value| value.as_str()))
+    resolve_owner_scope_notification_user(
+        metadata.get("notify_user").and_then(|value| value.as_str()),
+        metadata.get("owner_id").and_then(|value| value.as_str()),
+    )
+}
+
+fn trimmed_option(value: Option<&str>) -> Option<String> {
+    value
         .map(str::trim)
         .filter(|value| !value.is_empty())
         .map(ToOwned::to_owned)
 }
 
+fn resolve_owner_scope_notification_user(
+    explicit_user: Option<&str>,
+    owner_fallback: Option<&str>,
+) -> Option<String> {
+    trimmed_option(explicit_user).or_else(|| trimmed_option(owner_fallback))
+}
+
+async fn resolve_channel_notification_user(
+    extension_manager: Option<&Arc<ExtensionManager>>,
+    channel: Option<&str>,
+    explicit_user: Option<&str>,
+    owner_fallback: Option<&str>,
+) -> Option<String> {
+    if let Some(user) = trimmed_option(explicit_user) {
+        return Some(user);
+    }
+
+    if let Some(channel_name) = trimmed_option(channel)
+        && let Some(extension_manager) = extension_manager
+        && let Some(target) = extension_manager
+            .notification_target_for_channel(&channel_name)
+            .await
+    {
+        return Some(target);
+    }
+
+    resolve_owner_scope_notification_user(explicit_user, owner_fallback)
+}
+
+async fn resolve_routine_notification_target(
+    extension_manager: Option<&Arc<ExtensionManager>>,
+    metadata: &serde_json::Value,
+) -> Option<String> {
+    resolve_channel_notification_user(
+        extension_manager,
+        metadata
+            .get("notify_channel")
+            .and_then(|value| value.as_str()),
+        metadata.get("notify_user").and_then(|value| value.as_str()),
+        metadata.get("owner_id").and_then(|value| value.as_str()),
+    )
+    .await
+}
+
 fn should_fallback_routine_notification(error: &ChannelError) -> bool {
     !matches!(error, ChannelError::MissingRoutingTarget { .. })
 }
@@ -395,11 +444,13 @@ impl Agent {
                         .timezone
                         .clone()
                         .or_else(|| Some(self.config.default_timezone.clone()));
-                    if let Some(channel) = &hb_config.notify_channel {
-                        let user = hb_config
-                            .notify_user
-                            .clone()
-                            .unwrap_or_else(|| self.owner_id().to_string());
+                    let heartbeat_notify_user = resolve_owner_scope_notification_user(
+                        hb_config.notify_user.as_deref(),
+                        Some(self.owner_id()),
+                    );
+                    if let Some(channel) = &hb_config.notify_channel
+                        && let Some(user) = heartbeat_notify_user.as_deref()
+                    {
                         config = config.with_notify(user, channel);
                     }
 
@@ -409,26 +460,32 @@ impl Agent {
 
                     // Spawn notification forwarder that routes through channel manager
                     let notify_channel = hb_config.notify_channel.clone();
-                    let notify_user = hb_config
-                        .notify_user
-                        .clone()
-                        .unwrap_or_else(|| self.owner_id().to_string());
+                    let notify_target = resolve_channel_notification_user(
+                        self.deps.extension_manager.as_ref(),
+                        hb_config.notify_channel.as_deref(),
+                        hb_config.notify_user.as_deref(),
+                        Some(self.owner_id()),
+                    )
+                    .await;
+                    let notify_user = heartbeat_notify_user;
                     let channels = self.channels.clone();
                     tokio::spawn(async move {
                         while let Some(response) = notify_rx.recv().await {
                             // Try the configured channel first, fall back to
                             // broadcasting on all channels.
-                            let targeted_ok = if let Some(ref channel) = notify_channel {
+                            let targeted_ok = if let Some(ref channel) = notify_channel
+                                && let Some(ref user) = notify_target
+                            {
                                 channels
-                                    .broadcast(channel, &notify_user, response.clone())
+                                    .broadcast(channel, user, response.clone())
                                     .await
                                     .is_ok()
                             } else {
                                 false
                             };
 
-                            if !targeted_ok {
-                                let results = channels.broadcast_all(&notify_user, response).await;
+                            if !targeted_ok && let Some(ref user) = notify_user {
+                                let results = channels.broadcast_all(user, response).await;
                                 for (ch, result) in results {
                                     if let Err(e) = result {
                                         tracing::warn!(
@@ -496,6 +553,7 @@ impl Agent {
 
                     // Spawn notification forwarder (mirrors heartbeat pattern)
                     let channels = self.channels.clone();
+                    let extension_manager = self.deps.extension_manager.clone();
                     tokio::spawn(async move {
                         while let Some(response) = notify_rx.recv().await {
                             let notify_channel = response
@@ -503,7 +561,18 @@ impl Agent {
                                 .get("notify_channel")
                                 .and_then(|v| v.as_str())
                                 .map(|s| s.to_string());
-                            let Some(user) = resolve_routine_notification_user(&response.metadata)
+                            let fallback_user = resolve_owner_scope_notification_user(
+                                response
+                                    .metadata
+                                    .get("notify_user")
+                                    .and_then(|v| v.as_str()),
+                                response.metadata.get("owner_id").and_then(|v| v.as_str()),
+                            );
+                            let Some(user) = resolve_routine_notification_target(
+                                extension_manager.as_ref(),
+                                &response.metadata,
+                            )
+                            .await
                             else {
                                 tracing::warn!(
                                     notify_channel = ?notify_channel,
@@ -537,7 +606,7 @@ impl Agent {
                                 false
                             };
 
-                            if !targeted_ok {
+                            if !targeted_ok && let Some(user) = fallback_user {
                                 let results = channels.broadcast_all(&user, response).await;
                                 for (ch, result) in results {
                                     if let Err(e) = result {
@@ -624,6 +693,29 @@ impl Agent {
             // Store successfully extracted document text in workspace for indexing
             self.store_extracted_documents(&message).await;
 
+            // Event-triggered routines consume plain user input before it enters
+            // the normal chat/tool pipeline. This avoids a duplicate turn where
+            // the main agent responds and the routine also fires on the same
+            // inbound message.
+            if !message.is_internal
+                && matches!(
+                    SubmissionParser::parse(&message.content),
+                    Submission::UserInput { .. }
+                )
+                && let Some(ref engine) = routine_engine_for_loop
+            {
+                let fired = engine.check_event_triggers(&message).await;
+                if fired > 0 {
+                    tracing::debug!(
+                        channel = %message.channel,
+                        user = %message.user_id,
+                        fired,
+                        "Consumed inbound user message with matching event-triggered routine(s)"
+                    );
+                    continue;
+                }
+            }
+
             match self.handle_message(&message).await {
                 Ok(Some(response)) if !response.is_empty() => {
                     // Hook: BeforeOutbound — allow hooks to modify or suppress outbound
@@ -696,14 +788,6 @@ impl Agent {
                     }
                 }
             }
-
-            // Check event triggers (cheap in-memory regex, fires async if matched)
-            if let Some(ref engine) = routine_engine_for_loop {
-                let fired = engine.check_event_triggers(&message).await;
-                if fired > 0 {
-                    tracing::debug!("Fired {} event-triggered routines", fired);
-                }
-            }
         }
 
         // Cleanup
diff --git a/src/channels/web/server.rs b/src/channels/web/server.rs
index 1eb49e3cf5..27ef7cdce9 100644
--- a/src/channels/web/server.rs
+++ b/src/channels/web/server.rs
@@ -2243,14 +2243,7 @@ async fn extensions_setup_submit_handler(
             resp.auth_url = result.auth_url.clone();
             resp.verification = result.verification.clone();
             resp.instructions = result.verification.as_ref().map(|v| v.instructions.clone());
-            if result.verification.is_some() {
-                state.sse.broadcast(SseEvent::AuthRequired {
-                    extension_name: name.clone(),
-                    instructions: resp.instructions.clone(),
-                    auth_url: None,
-                    setup_url: None,
-                });
-            } else {
+            if result.verification.is_none() {
                 // Broadcast auth_completed so the chat UI can dismiss any in-progress
                 // auth card or setup modal that was triggered by tool_auth/tool_activate.
                 state.sse.broadcast(SseEvent::AuthCompleted {
@@ -2981,6 +2974,92 @@ mod tests {
         );
     }
 
+    #[tokio::test]
+    async fn test_extensions_setup_submit_telegram_verification_does_not_broadcast_auth_required() {
+        use axum::body::Body;
+        use tokio::time::{Duration, timeout};
+        use tower::ServiceExt;
+
+        let secrets = test_secrets_store();
+        let (ext_mgr, _wasm_tools_dir, wasm_channels_dir) = test_ext_mgr(secrets);
+
+        std::fs::write(
+            wasm_channels_dir.path().join("telegram.wasm"),
+            b"\0asm fake",
+        )
+        .expect("write fake telegram wasm");
+        let caps = serde_json::json!({
+            "type": "channel",
+            "name": "telegram",
+            "setup": {
+                "required_secrets": [
+                    {
+                        "name": "telegram_bot_token",
+                        "prompt": "Enter your Telegram Bot API token (from @BotFather)"
+                    }
+                ]
+            }
+        });
+        std::fs::write(
+            wasm_channels_dir.path().join("telegram.capabilities.json"),
+            serde_json::to_string(&caps).expect("serialize telegram caps"),
+        )
+        .expect("write telegram caps");
+
+        ext_mgr
+            .set_test_telegram_pending_verification("iclaw-7qk2m9", Some("test_hot_bot"))
+            .await;
+
+        let state = test_gateway_state(Some(ext_mgr));
+        let mut receiver = state.sse.sender().subscribe();
+        let app = Router::new()
+            .route(
+                "/api/extensions/{name}/setup",
+                post(extensions_setup_submit_handler),
+            )
+            .with_state(state);
+
+        let req_body = serde_json::json!({
+            "secrets": {
+                "telegram_bot_token": "123456789:ABCdefGhI"
+            }
+        });
+        let req = axum::http::Request::builder()
+            .method("POST")
+            .uri("/api/extensions/telegram/setup")
+            .header("content-type", "application/json")
+            .body(Body::from(req_body.to_string()))
+            .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 parsed: serde_json::Value = serde_json::from_slice(&body).expect("json response");
+        assert_eq!(parsed["success"], serde_json::Value::Bool(true));
+        assert_eq!(parsed["activated"], serde_json::Value::Bool(false));
+        assert_eq!(parsed["verification"]["code"], "iclaw-7qk2m9");
+
+        let deadline = tokio::time::Instant::now() + Duration::from_millis(100);
+        loop {
+            let remaining = deadline.saturating_duration_since(tokio::time::Instant::now());
+            if remaining.is_zero() {
+                break;
+            }
+            match timeout(remaining, receiver.recv()).await {
+                Ok(Ok(crate::channels::web::types::SseEvent::AuthRequired { .. })) => {
+                    panic!("verification responses should not emit auth_required SSE events")
+                }
+                Ok(Ok(_)) => continue,
+                Ok(Err(_)) | Err(_) => break,
+            }
+        }
+    }
+
     fn expired_flow_created_at() -> Option<std::time::Instant> {
         std::time::Instant::now()
             .checked_sub(oauth_defaults::OAUTH_FLOW_EXPIRY + std::time::Duration::from_secs(1))
diff --git a/src/channels/web/static/app.js b/src/channels/web/static/app.js
index 127c18fa0c..9d931500cd 100644
--- a/src/channels/web/static/app.js
+++ b/src/channels/web/static/app.js
@@ -527,7 +527,6 @@ function enableChatInput() {
   const btn = document.getElementById('send-btn');
   if (input) {
     input.disabled = false;
-    input.placeholder = I18n.t('chat.inputPlaceholder');
   }
   if (btn) btn.disabled = false;
 }
@@ -1205,11 +1204,13 @@ function showJobCard(data) {
 // --- Auth card ---
 
 function handleAuthRequired(data) {
-  setAuthFlowPending(true, data.instructions);
   if (data.auth_url) {
+    setAuthFlowPending(true, data.instructions);
     // OAuth flow: show the global auth prompt with an OAuth button + optional token paste field.
     showAuthCard(data);
   } else {
+    if (getConfigureOverlay(data.extension_name)) return;
+    setAuthFlowPending(true, data.instructions);
     // Setup flow: fetch the extension's credential schema and show the multi-field
     // configure modal (the same UI used by the Extensions tab "Setup" button).
     showConfigureModal(data.extension_name);
@@ -1433,13 +1434,11 @@ function setAuthFlowPending(pending, instructions) {
   if (authFlowPending) {
     input.disabled = true;
     btn.disabled = true;
-    input.placeholder = instructions || 'Complete extension auth to continue chatting';
     return;
   }
   if (!currentThreadIsReadOnly) {
     input.disabled = false;
     btn.disabled = false;
-    input.placeholder = I18n.t('chat.inputPlaceholder');
   }
 }
 
@@ -2712,8 +2711,11 @@ function renderConfigureModal(name, secrets) {
   const overlay = document.createElement('div');
   overlay.className = 'configure-overlay';
   overlay.setAttribute('data-extension-name', name);
+  overlay.dataset.telegramVerificationState = 'idle';
   overlay.addEventListener('click', (e) => {
-    if (e.target === overlay) closeConfigureModal();
+    if (e.target !== overlay) return;
+    if (name === 'telegram' && overlay.dataset.telegramVerificationState === 'waiting') return;
+    closeConfigureModal();
   });
 
   const modal = document.createElement('div');
@@ -2737,6 +2739,7 @@ function renderConfigureModal(name, secrets) {
   for (const secret of secrets) {
     const field = document.createElement('div');
     field.className = 'configure-field';
+    field.dataset.secretName = secret.name;
 
     const label = document.createElement('label');
     label.textContent = secret.prompt;
@@ -2781,6 +2784,16 @@ function renderConfigureModal(name, secrets) {
 
   modal.appendChild(form);
 
+  const error = document.createElement('div');
+  error.className = 'configure-inline-error';
+  error.style.display = 'none';
+  modal.appendChild(error);
+
+  const status = document.createElement('div');
+  status.className = 'configure-inline-status';
+  status.style.display = 'none';
+  modal.appendChild(status);
+
   const actions = document.createElement('div');
   actions.className = 'configure-actions';
 
@@ -2807,12 +2820,20 @@ function renderTelegramVerificationChallenge(overlay, verification) {
   if (!overlay || !verification) return;
   const modal = overlay.querySelector('.configure-modal');
   if (!modal) return;
+  const telegramField = modal.querySelector('.configure-field[data-secret-name="telegram_bot_token"]');
 
   let panel = modal.querySelector('.configure-verification');
   if (!panel) {
     panel = document.createElement('div');
     panel.className = 'configure-verification';
-    modal.insertBefore(panel, modal.querySelector('.configure-actions'));
+  }
+  if (telegramField && telegramField.parentNode) {
+    telegramField.insertAdjacentElement('afterend', panel);
+  } else {
+    modal.insertBefore(
+      panel,
+      modal.querySelector('.configure-inline-error') || modal.querySelector('.configure-actions')
+    );
   }
 
   panel.innerHTML = '';
@@ -2827,10 +2848,15 @@ function renderTelegramVerificationChallenge(overlay, verification) {
   instructions.textContent = verification.instructions;
   panel.appendChild(instructions);
 
-  const code = document.createElement('code');
-  code.className = 'configure-verification-code';
-  code.textContent = verification.code;
-  panel.appendChild(code);
+  const commandLabel = document.createElement('div');
+  commandLabel.className = 'configure-verification-instructions';
+  commandLabel.textContent = I18n.t('config.telegramCommandLabel');
+  panel.appendChild(commandLabel);
+
+  const command = document.createElement('code');
+  command.className = 'configure-verification-code';
+  command.textContent = '/start ' + verification.code;
+  panel.appendChild(command);
 
   if (verification.deep_link) {
     const link = document.createElement('a');
@@ -2843,7 +2869,57 @@ function renderTelegramVerificationChallenge(overlay, verification) {
   }
 }
 
-function submitConfigureModal(name, fields) {
+function getConfigurePrimaryButton(overlay) {
+  return overlay && overlay.querySelector('.configure-actions button.btn-ext.activate');
+}
+
+function getConfigureCancelButton(overlay) {
+  return overlay && overlay.querySelector('.configure-actions button.btn-ext.remove');
+}
+
+function setConfigureInlineError(overlay, message) {
+  const error = overlay && overlay.querySelector('.configure-inline-error');
+  if (!error) return;
+  error.textContent = message || '';
+  error.style.display = message ? 'block' : 'none';
+}
+
+function clearConfigureInlineError(overlay) {
+  setConfigureInlineError(overlay, '');
+}
+
+function setConfigureInlineStatus(overlay, message) {
+  const status = overlay && overlay.querySelector('.configure-inline-status');
+  if (!status) return;
+  status.textContent = message || '';
+  status.style.display = message ? 'block' : 'none';
+}
+
+function setTelegramConfigureState(overlay, fields, state) {
+  if (!overlay) return;
+  overlay.dataset.telegramVerificationState = state;
+
+  const primaryBtn = getConfigurePrimaryButton(overlay);
+  const cancelBtn = getConfigureCancelButton(overlay);
+  const waiting = state === 'waiting';
+  const retry = state === 'retry';
+
+  setConfigureInlineStatus(overlay, waiting ? I18n.t('config.telegramOwnerWaiting') : '');
+
+  if (primaryBtn) {
+    primaryBtn.style.display = waiting ? 'none' : '';
+    primaryBtn.disabled = false;
+    primaryBtn.textContent = retry ? I18n.t('config.telegramStartOver') : I18n.t('config.save');
+  }
+  if (cancelBtn) cancelBtn.disabled = waiting;
+}
+
+function startTelegramAutoVerify(name, fields) {
+  window.setTimeout(() => submitConfigureModal(name, fields, { telegramAutoVerify: true }), 0);
+}
+
+function submitConfigureModal(name, fields, options) {
+  options = options || {};
   const secrets = {};
   for (const f of fields) {
     if (f.input.value.trim()) {
@@ -2851,13 +2927,15 @@ function submitConfigureModal(name, fields) {
     }
   }
 
-  // Disable buttons to prevent double-submit
   const overlay = getConfigureOverlay(name) || document.querySelector('.configure-overlay');
+  const isTelegram = name === 'telegram';
+  clearConfigureInlineError(overlay);
+
+  // Disable buttons to prevent double-submit
   var btns = overlay ? overlay.querySelectorAll('.configure-actions button') : [];
   btns.forEach(function(b) { b.disabled = true; });
-  if (overlay && name === 'telegram') {
-    const submitBtn = overlay.querySelector('.configure-actions button.btn-ext.activate');
-    if (submitBtn) submitBtn.textContent = I18n.t('config.telegramOwnerWaiting');
+  if (overlay && isTelegram) {
+    setTelegramConfigureState(overlay, fields, 'waiting');
   }
 
   apiFetch('/api/extensions/' + encodeURIComponent(name) + '/setup', {
@@ -2866,13 +2944,20 @@ function submitConfigureModal(name, fields) {
   })
     .then((res) => {
       if (res.success) {
-        if (res.verification && name === 'telegram') {
-          btns.forEach(function(b) { b.disabled = false; });
+        if (res.verification && isTelegram) {
           renderTelegramVerificationChallenge(overlay, res.verification);
           fields.forEach(function(f) { f.input.value = ''; });
-          const submitBtn = overlay.querySelector('.configure-actions button.btn-ext.activate');
-          if (submitBtn) submitBtn.textContent = I18n.t('config.telegramVerifyOwner');
-          showToast(res.message || res.verification.instructions, 'info');
+          setTelegramConfigureState(overlay, fields, 'waiting');
+          // Once the verification challenge is rendered inline, the global auth lock
+          // should not keep the chat composer disabled for this setup-driven flow.
+          setAuthFlowPending(false);
+          enableChatInput();
+          if (!options.telegramAutoVerify) {
+            startTelegramAutoVerify(name, fields);
+            return;
+          }
+          setTelegramConfigureState(overlay, fields, 'retry');
+          setConfigureInlineError(overlay, I18n.t('config.telegramStartOverHint'));
           return;
         }
 
@@ -2891,13 +2976,13 @@ function submitConfigureModal(name, fields) {
       } else {
         // Keep modal open so the user can correct their input and retry.
         btns.forEach(function(b) { b.disabled = false; });
-        if (name === 'telegram') {
-          const submitBtn = overlay && overlay.querySelector('.configure-actions button.btn-ext.activate');
+        setConfigureInlineError(overlay, res.message || 'Configuration failed');
+        if (isTelegram) {
           const hasVerification = overlay && overlay.querySelector('.configure-verification');
-          if (submitBtn) {
-            submitBtn.textContent = hasVerification
-              ? I18n.t('config.telegramVerifyOwner')
-              : I18n.t('config.save');
+          if (options.telegramAutoVerify || hasVerification) {
+            setTelegramConfigureState(overlay, fields, 'retry');
+          } else {
+            setTelegramConfigureState(overlay, fields, 'idle');
           }
         }
         showToast(res.message || 'Configuration failed', 'error');
@@ -2905,13 +2990,13 @@ function submitConfigureModal(name, fields) {
     })
     .catch((err) => {
       btns.forEach(function(b) { b.disabled = false; });
-      if (name === 'telegram') {
-        const submitBtn = overlay && overlay.querySelector('.configure-actions button.btn-ext.activate');
+      setConfigureInlineError(overlay, 'Configuration failed: ' + err.message);
+      if (isTelegram) {
         const hasVerification = overlay && overlay.querySelector('.configure-verification');
-        if (submitBtn) {
-          submitBtn.textContent = hasVerification
-            ? I18n.t('config.telegramVerifyOwner')
-            : I18n.t('config.save');
+        if (options.telegramAutoVerify || hasVerification) {
+          setTelegramConfigureState(overlay, fields, 'retry');
+        } else {
+          setTelegramConfigureState(overlay, fields, 'idle');
         }
       }
       showToast('Configuration failed: ' + err.message, 'error');
@@ -2922,6 +3007,10 @@ function closeConfigureModal(extensionName) {
   if (typeof extensionName !== 'string') extensionName = null;
   const existing = getConfigureOverlay(extensionName);
   if (existing) existing.remove();
+  if (!document.querySelector('.configure-overlay') && !document.querySelector('.auth-card')) {
+    setAuthFlowPending(false);
+    enableChatInput();
+  }
 }
 
 // Validate that a server-supplied OAuth URL is HTTPS before opening a popup.
diff --git a/src/channels/web/static/i18n/en.js b/src/channels/web/static/i18n/en.js
index 42e996da0a..49bec76204 100644
--- a/src/channels/web/static/i18n/en.js
+++ b/src/channels/web/static/i18n/en.js
@@ -342,10 +342,12 @@ I18n.register('en', {
   
   // Configure
   'config.title': 'Configure {name}',
-  'config.telegramOwnerHint': 'After saving, IronClaw will show a one-time code. Send `/start CODE` to your bot in Telegram, then click Verify owner.',
+  'config.telegramOwnerHint': 'After saving, IronClaw will show a one-time code. Send `/start CODE` to your bot in Telegram and IronClaw will finish setup automatically.',
   'config.telegramChallengeTitle': 'Telegram owner verification',
   'config.telegramOwnerWaiting': 'Waiting for Telegram owner verification...',
-  'config.telegramVerifyOwner': 'Verify owner',
+  'config.telegramCommandLabel': 'Send this in Telegram:',
+  'config.telegramStartOver': 'Start over',
+  'config.telegramStartOverHint': 'Telegram verification did not complete. Click Start over to generate a new code and try again.',
   'config.telegramOpenBot': 'Open bot in Telegram',
   'config.optional': ' (optional)',
   'config.alreadySet': '(already set — leave empty to keep)',
diff --git a/src/channels/web/static/i18n/zh-CN.js b/src/channels/web/static/i18n/zh-CN.js
index 8a7fd520c4..d31cc0df91 100644
--- a/src/channels/web/static/i18n/zh-CN.js
+++ b/src/channels/web/static/i18n/zh-CN.js
@@ -342,6 +342,12 @@ I18n.register('zh-CN', {
   
   // 配置
   'config.title': '配置 {name}',
+  'config.telegramOwnerHint': '保存后，IronClaw 会显示一次性验证码。将 `/start CODE` 发送给你的 Telegram 机器人，IronClaw 会自动完成设置。',
+  'config.telegramChallengeTitle': 'Telegram 所有者验证',
+  'config.telegramOwnerWaiting': '正在等待 Telegram 所有者验证...',
+  'config.telegramCommandLabel': '请在 Telegram 中发送：',
+  'config.telegramStartOver': '重新开始',
+  'config.telegramStartOverHint': 'Telegram 验证未完成。点击“重新开始”以生成新的验证码并重试。',
   'config.optional': '（可选）',
   'config.alreadySet': '（已设置 — 留空以保持不变）',
   'config.alreadyConfigured': '已配置',
diff --git a/src/channels/web/static/style.css b/src/channels/web/static/style.css
index 44fd91762f..06d9665a20 100644
--- a/src/channels/web/static/style.css
+++ b/src/channels/web/static/style.css
@@ -2952,6 +2952,28 @@ body {
   text-decoration: underline;
 }
 
+.configure-inline-error {
+  margin: 16px 0 0 0;
+  padding: 10px 12px;
+  border-radius: 8px;
+  background: rgba(220, 38, 38, 0.12);
+  border: 1px solid rgba(220, 38, 38, 0.35);
+  color: #fca5a5;
+  font-size: 13px;
+  line-height: 1.5;
+}
+
+.configure-inline-status {
+  margin: 16px 0 0 0;
+  padding: 10px 12px;
+  border-radius: 8px;
+  background: var(--bg-secondary);
+  border: 1px solid var(--border);
+  color: var(--text-secondary);
+  font-size: 13px;
+  line-height: 1.5;
+}
+
 .configure-form {
   display: flex;
   flex-direction: column;
diff --git a/src/extensions/manager.rs b/src/extensions/manager.rs
index 471f10cf89..00d787a5a3 100644
--- a/src/extensions/manager.rs
+++ b/src/extensions/manager.rs
@@ -140,6 +140,13 @@ struct TelegramGetUpdatesResponse {
     description: Option<String>,
 }
 
+#[derive(Debug, serde::Deserialize)]
+struct TelegramApiOkResponse {
+    ok: bool,
+    #[serde(default)]
+    description: Option<String>,
+}
+
 #[derive(Debug, serde::Deserialize)]
 struct TelegramUpdate {
     update_id: i64,
@@ -204,7 +211,7 @@ fn channel_auth_instructions(
 ) -> String {
     if channel_name == TELEGRAM_CHANNEL_NAME && secret.name == "telegram_bot_token" {
         return format!(
-            "{} After you submit it, IronClaw will show a one-time verification code. Send `/start CODE` to your bot in Telegram, then verify again to bind the owner.",
+            "{} After you submit it, IronClaw will show a one-time verification code. Send `/start CODE` to your bot in Telegram and IronClaw will finish setup automatically.",
             secret.prompt
         );
     }
@@ -237,10 +244,12 @@ fn telegram_verification_deep_link(bot_username: Option<&str>, code: &str) -> Op
 
 fn telegram_verification_instructions(bot_username: Option<&str>, code: &str) -> String {
     if let Some(username) = bot_username.filter(|username| !username.trim().is_empty()) {
-        return format!("Send `/start {code}` to @{username}, then click Verify owner.");
+        return format!(
+            "Send `/start {code}` to @{username} in Telegram. IronClaw will finish setup automatically."
+        );
     }
 
-    format!("Send `/start {code}` to your Telegram bot, then click Verify owner.")
+    format!("Send `/start {code}` to your Telegram bot. IronClaw will finish setup automatically.")
 }
 
 fn telegram_message_matches_verification_code(text: &str, code: &str) -> bool {
@@ -253,6 +262,42 @@ fn telegram_message_matches_verification_code(text: &str, code: &str) -> bool {
             .any(|token| token == code)
 }
 
+async fn send_telegram_text_message(
+    client: &reqwest::Client,
+    endpoint: &str,
+    chat_id: i64,
+    text: &str,
+) -> Result<(), ExtensionError> {
+    let response = client
+        .post(endpoint)
+        .json(&serde_json::json!({
+            "chat_id": chat_id,
+            "text": text,
+        }))
+        .send()
+        .await
+        .map_err(|e| telegram_request_error("sendMessage", &e))?;
+
+    if !response.status().is_success() {
+        return Err(ExtensionError::Other(format!(
+            "Telegram sendMessage failed (HTTP {})",
+            response.status()
+        )));
+    }
+
+    let payload: TelegramApiOkResponse = response
+        .json()
+        .await
+        .map_err(|e| telegram_response_parse_error("sendMessage", &e))?;
+    if !payload.ok {
+        return Err(ExtensionError::Other(payload.description.unwrap_or_else(
+            || "Telegram sendMessage returned ok=false".to_string(),
+        )));
+    }
+
+    Ok(())
+}
+
 /// Central manager for extension lifecycle operations.
 ///
 /// # Initialization Order
@@ -421,6 +466,29 @@ impl ExtensionManager {
         *self.test_telegram_binding_resolver.write().await = Some(resolver);
     }
 
+    #[cfg(test)]
+    pub(crate) async fn set_test_telegram_pending_verification(
+        &self,
+        code: &str,
+        bot_username: Option<&str>,
+    ) {
+        let code = code.to_string();
+        let bot_username = bot_username.map(str::to_string);
+        self.set_test_telegram_binding_resolver(Arc::new(move |_token, existing_owner_id| {
+            if existing_owner_id.is_some() {
+                return Err(ExtensionError::Other(
+                    "unexpected existing owner binding".to_string(),
+                ));
+            }
+            Ok(TelegramBindingResult::Pending(VerificationChallenge {
+                code: code.clone(),
+                instructions: telegram_verification_instructions(bot_username.as_deref(), &code),
+                deep_link: telegram_verification_deep_link(bot_username.as_deref(), &code),
+            }))
+        }))
+        .await;
+    }
+
     /// Enable gateway mode so OAuth flows return auth URLs to the frontend
     /// instead of calling `open::that()` on the server.
     ///
@@ -597,6 +665,12 @@ impl ExtensionManager {
         self.current_channel_owner_id(name).await.is_some()
     }
 
+    pub(crate) async fn notification_target_for_channel(&self, name: &str) -> Option<String> {
+        self.current_channel_owner_id(name)
+            .await
+            .map(|owner_id| owner_id.to_string())
+    }
+
     async fn get_pending_telegram_verification(
         &self,
         name: &str,
@@ -1074,7 +1148,7 @@ impl ExtensionManager {
                             active,
                             tools: Vec::new(),
                             needs_setup: auth_state == ToolAuthState::NeedsSetup,
-                            has_auth: false,
+                            has_auth: auth_state != ToolAuthState::NoAuth,
                             installed: true,
                             activation_error,
                             version,
@@ -4336,6 +4410,22 @@ impl ExtensionManager {
             }
 
             if let Some(owner_id) = bound_owner_id {
+                if let Err(err) = send_telegram_text_message(
+                    &client,
+                    &format!("https://api.telegram.org/bot{bot_token}/sendMessage"),
+                    owner_id,
+                    "Verification received. Finishing setup...",
+                )
+                .await
+                {
+                    tracing::warn!(
+                        channel = name,
+                        owner_id,
+                        error = %err,
+                        "Failed to send Telegram verification acknowledgment"
+                    );
+                }
+
                 self.clear_pending_telegram_verification(name).await;
                 if offset > 0 {
                     let _ = client
@@ -4355,10 +4445,10 @@ impl ExtensionManager {
             }
         }
 
-        Err(ExtensionError::ValidationFailed(format!(
-            "Telegram owner verification timed out. Send `/start {}` to your bot, then click Verify owner again.",
-            challenge.code
-        )))
+        self.clear_pending_telegram_verification(name).await;
+        Err(ExtensionError::ValidationFailed(
+            "Telegram owner verification timed out. Request a new code and try again.".to_string(),
+        ))
     }
 
     async fn notify_telegram_owner_verified(
@@ -5120,7 +5210,7 @@ mod tests {
     use crate::extensions::manager::{
         ChannelRuntimeState, FallbackDecision, TelegramBindingData, TelegramBindingResult,
         TelegramOwnerBindingState, build_wasm_channel_runtime_config_updates,
-        combine_install_errors, fallback_decision, infer_kind_from_url,
+        combine_install_errors, fallback_decision, infer_kind_from_url, send_telegram_text_message,
         telegram_message_matches_verification_code,
     };
     use crate::extensions::{
@@ -5923,7 +6013,7 @@ mod tests {
                 Ok(TelegramBindingResult::Pending(VerificationChallenge {
                     code: "iclaw-7qk2m9".to_string(),
                     instructions:
-                        "Send `/start iclaw-7qk2m9` to @test_hot_bot, then click Verify owner."
+                        "Send `/start iclaw-7qk2m9` to @test_hot_bot in Telegram. IronClaw will finish setup automatically."
                             .to_string(),
                     deep_link: Some("https://t.me/test_hot_bot?start=iclaw-7qk2m9".to_string()),
                 }))
@@ -6875,11 +6965,75 @@ mod tests {
         )?;
         require(
             instructions.contains("one-time verification code")
-                && instructions.contains("/start CODE"),
+                && instructions.contains("/start CODE")
+                && instructions.contains("finish setup automatically"),
             "telegram auth instructions should explain the owner verification step",
         )
     }
 
+    #[tokio::test]
+    async fn test_send_telegram_text_message_posts_expected_payload() -> Result<(), String> {
+        use axum::{Json, Router, extract::State, routing::post};
+
+        let payloads = Arc::new(tokio::sync::Mutex::new(Vec::<serde_json::Value>::new()));
+
+        async fn handler(
+            State(payloads): State<Arc<tokio::sync::Mutex<Vec<serde_json::Value>>>>,
+            Json(payload): Json<serde_json::Value>,
+        ) -> Json<serde_json::Value> {
+            payloads.lock().await.push(payload);
+            Json(serde_json::json!({ "ok": true, "result": {} }))
+        }
+
+        let app = Router::new()
+            .route("/sendMessage", post(handler))
+            .with_state(Arc::clone(&payloads));
+        let listener = tokio::net::TcpListener::bind("127.0.0.1:0")
+            .await
+            .map_err(|err| format!("bind listener: {err}"))?;
+        let addr = listener
+            .local_addr()
+            .map_err(|err| format!("listener addr: {err}"))?;
+        let server = tokio::spawn(async move {
+            let _ = axum::serve(listener, app).await;
+        });
+
+        let client = reqwest::Client::new();
+        send_telegram_text_message(
+            &client,
+            &format!("http://{addr}/sendMessage"),
+            424242,
+            "Verification received. Finishing setup...",
+        )
+        .await
+        .map_err(|err| format!("send message: {err}"))?;
+
+        let captured = tokio::time::timeout(std::time::Duration::from_secs(1), async {
+            loop {
+                let maybe_payload = { payloads.lock().await.first().cloned() };
+                if let Some(payload) = maybe_payload {
+                    break payload;
+                }
+                tokio::time::sleep(std::time::Duration::from_millis(10)).await;
+            }
+        })
+        .await
+        .map_err(|_| "timed out waiting for sendMessage payload".to_string())?;
+
+        server.abort();
+
+        require_eq(
+            captured["chat_id"].clone(),
+            serde_json::json!(424242),
+            "chat_id",
+        )?;
+        require_eq(
+            captured["text"].clone(),
+            serde_json::json!("Verification received. Finishing setup..."),
+            "text",
+        )
+    }
+
     #[test]
     fn test_telegram_message_matches_verification_code_variants() -> Result<(), String> {
         require(
diff --git a/src/main.rs b/src/main.rs
index ae864bed9b..745cae09b4 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -620,7 +620,7 @@ async fn async_main() -> anyhow::Result<()> {
     // Register message tool for sending messages to connected channels
     components
         .tools
-        .register_message_tools(Arc::clone(&channels))
+        .register_message_tools(Arc::clone(&channels), components.extension_manager.clone())
         .await;
 
     // Wire up channel runtime for hot-activation of WASM channels.
diff --git a/src/tools/builtin/message.rs b/src/tools/builtin/message.rs
index b150c951e1..1d2ed0594a 100644
--- a/src/tools/builtin/message.rs
+++ b/src/tools/builtin/message.rs
@@ -10,6 +10,7 @@ use async_trait::async_trait;
 use crate::bootstrap::ironclaw_base_dir;
 use crate::channels::{ChannelManager, OutgoingResponse};
 use crate::context::JobContext;
+use crate::extensions::ExtensionManager;
 use crate::tools::tool::{
     ApprovalRequirement, Tool, ToolError, ToolOutput, ToolRateLimitConfig, require_str,
 };
@@ -17,6 +18,7 @@ use crate::tools::tool::{
 /// Tool for sending messages to channels.
 pub struct MessageTool {
     channel_manager: Arc<ChannelManager>,
+    extension_manager: Option<Arc<ExtensionManager>>,
     /// Default channel for current conversation (set per-turn).
     /// Uses std::sync::RwLock because requires_approval() is sync and called from async context.
     default_channel: Arc<RwLock<Option<String>>>,
@@ -32,12 +34,18 @@ impl MessageTool {
 
         Self {
             channel_manager,
+            extension_manager: None,
             default_channel: Arc::new(RwLock::new(None)),
             default_target: Arc::new(RwLock::new(None)),
             base_dir,
         }
     }
 
+    pub fn with_extension_manager(mut self, extension_manager: Arc<ExtensionManager>) -> Self {
+        self.extension_manager = Some(extension_manager);
+        self
+    }
+
     /// Set the base directory for attachment validation.
     /// This is primarily used for testing or future configuration.
     pub fn with_base_dir(mut self, dir: PathBuf) -> Self {
@@ -111,39 +119,69 @@ impl Tool for MessageTool {
 
         let content = require_str(&params, "content")?;
 
+        let explicit_channel = params
+            .get("channel")
+            .and_then(|v| v.as_str())
+            .map(|value| value.to_string());
+        let default_channel = self
+            .default_channel
+            .read()
+            .unwrap_or_else(|e| e.into_inner())
+            .clone();
+        let metadata_channel = ctx
+            .metadata
+            .get("notify_channel")
+            .and_then(|v| v.as_str())
+            .map(|value| value.to_string());
+
         // Get channel: use param → conversation default → job metadata → None (broadcast all)
-        let channel: Option<String> =
-            if let Some(c) = params.get("channel").and_then(|v| v.as_str()) {
-                Some(c.to_string())
-            } else if let Some(c) = self
-                .default_channel
-                .read()
-                .unwrap_or_else(|e| e.into_inner())
-                .clone()
-            {
-                Some(c)
-            } else {
-                ctx.metadata
-                    .get("notify_channel")
-                    .and_then(|v| v.as_str())
-                    .map(|c| c.to_string())
-            };
+        let channel: Option<String> = explicit_channel
+            .clone()
+            .or_else(|| default_channel.clone())
+            .or_else(|| metadata_channel.clone());
+
+        let can_use_default_target = match (explicit_channel.as_deref(), default_channel.as_deref())
+        {
+            (None, _) => true,
+            (Some(explicit), Some(current)) if explicit == current => true,
+            _ => false,
+        };
+        let can_use_metadata_target = match (channel.as_deref(), metadata_channel.as_deref()) {
+            (None, _) => true,
+            (Some(resolved), Some(current)) if resolved == current => true,
+            _ => false,
+        };
 
         // Get target: use param → conversation default → job metadata → owner scope
         // fallback when a specific channel is known.
         let target = if let Some(t) = params.get("target").and_then(|v| v.as_str()) {
             Some(t.to_string())
-        } else if let Some(t) = self
-            .default_target
-            .read()
-            .unwrap_or_else(|e| e.into_inner())
-            .clone()
+        } else if can_use_default_target
+            && let Some(t) = self
+                .default_target
+                .read()
+                .unwrap_or_else(|e| e.into_inner())
+                .clone()
         {
             Some(t)
-        } else if let Some(t) = ctx.metadata.get("notify_user").and_then(|v| v.as_str()) {
+        } else if can_use_metadata_target
+            && let Some(t) = ctx.metadata.get("notify_user").and_then(|v| v.as_str())
+        {
             Some(t.to_string())
         } else if channel.is_some() {
-            Some(ctx.user_id.clone())
+            if let Some(channel_name) = channel.as_deref() {
+                if let Some(extension_manager) = self.extension_manager.as_ref()
+                    && let Some(target) = extension_manager
+                        .notification_target_for_channel(channel_name)
+                        .await
+                {
+                    Some(target)
+                } else {
+                    Some(ctx.user_id.clone())
+                }
+            } else {
+                Some(ctx.user_id.clone())
+            }
         } else {
             None
         };
@@ -742,4 +780,33 @@ mod tests {
             err
         );
     }
+
+    #[tokio::test]
+    async fn message_tool_does_not_apply_metadata_target_to_different_default_channel() {
+        let tool = MessageTool::new(Arc::new(ChannelManager::new()));
+        tool.set_context(Some("telegram".to_string()), None).await;
+
+        let mut ctx = crate::context::JobContext::with_user("owner-scope", "test", "test");
+        ctx.metadata = serde_json::json!({
+            "notify_channel": "signal",
+            "notify_user": "metadata-user",
+        });
+
+        let result = tool
+            .execute(serde_json::json!({"content": "hello"}), &ctx)
+            .await;
+
+        assert!(result.is_err());
+        let err = result.unwrap_err().to_string();
+        assert!(
+            !err.contains("metadata-user"),
+            "metadata target should not be applied to a different default channel: {}",
+            err
+        );
+        assert!(
+            err.contains("owner-scope"),
+            "expected owner-scope fallback target when metadata channel differs: {}",
+            err
+        );
+    }
 }
diff --git a/src/tools/registry.rs b/src/tools/registry.rs
index 754869c8cf..0c457a6d3c 100644
--- a/src/tools/registry.rs
+++ b/src/tools/registry.rs
@@ -501,9 +501,14 @@ impl ToolRegistry {
     pub async fn register_message_tools(
         &self,
         channel_manager: Arc<crate::channels::ChannelManager>,
+        extension_manager: Option<Arc<crate::extensions::ExtensionManager>>,
     ) {
         use crate::tools::builtin::MessageTool;
-        let tool = Arc::new(MessageTool::new(channel_manager));
+        let mut tool = MessageTool::new(channel_manager);
+        if let Some(extension_manager) = extension_manager {
+            tool = tool.with_extension_manager(extension_manager);
+        }
+        let tool = Arc::new(tool);
         *self.message_tool.write().await = Some(Arc::clone(&tool));
         self.tools
             .write()
diff --git a/tests/e2e/CLAUDE.md b/tests/e2e/CLAUDE.md
index c977b6fdf8..0cf5e6dc32 100644
--- a/tests/e2e/CLAUDE.md
+++ b/tests/e2e/CLAUDE.md
@@ -52,7 +52,7 @@ HEADED=1 pytest scenarios/
 | `test_html_injection.py` | XSS vectors injected directly via `page.evaluate("addMessage('assistant', ...)")` are sanitized by `renderMarkdown`; user messages are shown as escaped plain text |
 | `test_skills.py` | Skills tab UI visibility, ClawHub search (skipped if registry unreachable), install + remove lifecycle |
 | `test_sse_reconnect.py` | SSE reconnects after programmatic `eventSource.close()` + `connectSSE()`; history is reloaded after reconnect |
-| `test_tool_approval.py` | Approval card appears, buttons disable on approve/deny, parameters toggle; all triggered via `page.evaluate("showApproval(...)")` — no real tool call needed |
+| `test_tool_approval.py` | Approval card appears, buttons disable on approve/deny, parameters toggle via `page.evaluate("showApproval(...)")`; the waiting-approval regression uses a real HTTP tool call |
 
 ## `helpers.py`
 
@@ -164,7 +164,7 @@ async def test_my_ui_feature(page):
 - **`asyncio_default_fixture_loop_scope = "session"`** — all async fixtures share one event loop. Do not use `asyncio.run()` inside fixtures; use `await` directly.
 - **The `page` fixture navigates with `/?token=e2e-test-token` and waits for `#auth-screen` to be hidden.** Tests receive a page that is already past the auth screen and has SSE connected.
 - **`test_skills.py` makes real network calls to ClawHub.** Tests skip (not fail) if the registry is unreachable via `pytest.skip()`.
-- **`test_html_injection.py` and `test_tool_approval.py` inject state via `page.evaluate(...)`.** They test the browser-side rendering pipeline and do not depend on the LLM or backend tool execution.
+- **`test_html_injection.py` injects state via `page.evaluate(...)`, and most of `test_tool_approval.py` does too.** The waiting-approval regression in `test_tool_approval.py` intentionally uses a real tool approval flow so it can verify backend thread-state handling.
 - **Browser is Chromium only.** `conftest.py` uses `p.chromium.launch()`; there is no Firefox or WebKit variant.
 - **Default timeout is 120 seconds** (pyproject.toml). Individual `wait_for` calls inside tests use shorter timeouts (5–20s) for faster failure messages.
 - **The libsql database is a temp directory** created fresh per `pytest` invocation; tests do not share state across runs.
diff --git a/tests/e2e/README.md b/tests/e2e/README.md
index 5aac9613fc..17e1378b73 100644
--- a/tests/e2e/README.md
+++ b/tests/e2e/README.md
@@ -164,5 +164,7 @@ await page.evaluate("""
 """)
 ```
 
-This is the pattern used in `test_tool_approval.py` and parts of
-`test_extensions.py` (auth card, configure modal).
+This is the pattern used in most of `test_tool_approval.py` and parts of
+`test_extensions.py` (auth card, configure modal). The waiting-approval
+regression in `test_tool_approval.py` uses a real tool call instead so it can
+exercise backend approval state.
diff --git a/tests/e2e/mock_llm.py b/tests/e2e/mock_llm.py
index b091fc1739..c27f276265 100644
--- a/tests/e2e/mock_llm.py
+++ b/tests/e2e/mock_llm.py
@@ -25,6 +25,15 @@
 
 TOOL_CALL_PATTERNS = [
     (re.compile(r"echo (.+)", re.IGNORECASE), "echo", lambda m: {"message": m.group(1)}),
+    (
+        re.compile(r"make approval post (?P<label>[a-z0-9_-]+)", re.IGNORECASE),
+        "http",
+        lambda m: {
+            "method": "POST",
+            "url": f"https://example.com/{m.group('label')}",
+            "body": {"label": m.group("label")},
+        },
+    ),
     (re.compile(r"what time|current time", re.IGNORECASE), "time", lambda _: {"operation": "now"}),
     (
         re.compile(
diff --git a/tests/e2e/scenarios/test_extensions.py b/tests/e2e/scenarios/test_extensions.py
index f172d42061..a728a9944f 100644
--- a/tests/e2e/scenarios/test_extensions.py
+++ b/tests/e2e/scenarios/test_extensions.py
@@ -885,6 +885,36 @@ async def test_auth_and_configure_helpers_escape_selector_sensitive_extension_na
     assert result["configureStillPresent"] is False
 
 
+async def test_auth_required_does_not_reopen_existing_configure_modal(page):
+    """Regression: auth_required SSE should not clobber an already-open configure modal."""
+    result = await page.evaluate(
+        """() => {
+            const overlay = document.createElement('div');
+            overlay.className = 'configure-overlay';
+            overlay.setAttribute('data-extension-name', 'telegram');
+            document.body.appendChild(overlay);
+
+            const originalShowConfigureModal = window.showConfigureModal;
+            const originalSetAuthFlowPending = window.setAuthFlowPending;
+            let showCalls = 0;
+            let pendingCalls = 0;
+
+            window.showConfigureModal = () => { showCalls += 1; };
+            window.setAuthFlowPending = () => { pendingCalls += 1; };
+
+            handleAuthRequired({ extension_name: 'telegram', instructions: 'pending', auth_url: null });
+
+            window.showConfigureModal = originalShowConfigureModal;
+            window.setAuthFlowPending = originalSetAuthFlowPending;
+            overlay.remove();
+            return { showCalls, pendingCalls };
+        }"""
+    )
+
+    assert result["showCalls"] == 0
+    assert result["pendingCalls"] == 0
+
+
 async def test_auth_completed_sse_dismisses_card(page):
     """Simulating the auth_completed SSE event removes the auth card."""
     await _show_auth_card(page, extension_name="myext")
diff --git a/tests/e2e/scenarios/test_telegram_hot_activation.py b/tests/e2e/scenarios/test_telegram_hot_activation.py
index 833803d650..e6fa598aac 100644
--- a/tests/e2e/scenarios/test_telegram_hot_activation.py
+++ b/tests/e2e/scenarios/test_telegram_hot_activation.py
@@ -125,6 +125,8 @@ async def test_telegram_hot_activation_transitions_installed_to_active(page):
     phase = {"value": "installed"}
     captured_setup_payloads = []
     post_count = {"value": 0}
+    second_request_started = asyncio.Event()
+    allow_second_response = asyncio.Event()
 
     async def handle_ext_list(route):
         extensions = {
@@ -170,16 +172,18 @@ async def handle_setup(route):
                     {
                         "success": True,
                         "activated": False,
-                        "message": "Configuration saved for 'telegram'. Send `/start iclaw-7qk2m9` to @test_hot_bot, then click Verify owner.",
+                        "message": "Configuration saved for 'telegram'. Send `/start iclaw-7qk2m9` to @test_hot_bot in Telegram. IronClaw will finish setup automatically.",
                         "verification": {
                             "code": "iclaw-7qk2m9",
-                            "instructions": "Send `/start iclaw-7qk2m9` to @test_hot_bot, then click Verify owner.",
+                            "instructions": "Send `/start iclaw-7qk2m9` to @test_hot_bot in Telegram. IronClaw will finish setup automatically.",
                             "deep_link": "https://t.me/test_hot_bot?start=iclaw-7qk2m9",
                         },
                     }
                 ),
             )
         else:
+            second_request_started.set()
+            await allow_second_response.wait()
             await route.fulfill(
                 status=200,
                 content_type="application/json",
@@ -203,16 +207,19 @@ async def handle_setup(route):
     await modal.wait_for(state="visible", timeout=5000)
     await modal.locator(_CONFIGURE_SECRET_INPUT).fill("123456789:ABCdefGhI")
     await modal.locator(_CONFIGURE_SAVE_BUTTON).click()
-    await modal.locator(_CONFIGURE_SAVE_BUTTON, has_text="Verify owner").wait_for(
+    await second_request_started.wait()
+    await modal.locator(".configure-inline-status", has_text="Waiting for Telegram owner verification...").wait_for(
         state="visible", timeout=5000
     )
-    assert "Verify owner" in (
-        await modal.locator(_CONFIGURE_SAVE_BUTTON).text_content()
-    )
     assert "iclaw-7qk2m9" in (await modal.text_content())
+    assert "/start iclaw-7qk2m9" in (await modal.text_content())
     assert await modal.locator(".configure-verification-link").count() == 1
+    await modal.locator(_CONFIGURE_SAVE_BUTTON).wait_for(state="hidden", timeout=5000)
 
-    await modal.locator(_CONFIGURE_SAVE_BUTTON).click()
+    await page.locator(SEL["configure_overlay"]).click(position={"x": 1, "y": 1})
+    assert await page.locator(SEL["configure_overlay"]).is_visible()
+
+    allow_second_response.set()
     await page.locator(SEL["configure_overlay"]).wait_for(state="hidden", timeout=5000)
 
     phase["value"] = "active"
diff --git a/tests/e2e/scenarios/test_tool_approval.py b/tests/e2e/scenarios/test_tool_approval.py
index 44418e469c..f3144e36c9 100644
--- a/tests/e2e/scenarios/test_tool_approval.py
+++ b/tests/e2e/scenarios/test_tool_approval.py
@@ -135,42 +135,39 @@ async def test_approval_params_toggle(page):
 async def test_waiting_for_approval_message_no_error_prefix(page):
     """Verify that input submitted while awaiting approval shows non-error status with tool context.
 
-    Tests the real flow: show approval card, then attempt to send input while approval is pending.
-    Backend rejects with Pending result (not Error), and message includes tool context.
+    Trigger a real approval-needed tool call, then attempt to send another message while
+    approval is pending. The backend should reject the second input with a non-error
+    status that includes the pending tool context.
     """
-    # First, inject an approval card to simulate the thread being in AwaitingApproval state
-    await page.evaluate("""
-        showApproval({
-            request_id: 'test-req-waiting-approval',
-            thread_id: currentThreadId,
-            tool_name: 'shell',
-            description: 'Execute: echo hello',
-            parameters: '{"command": "echo hello"}'
-        })
-    """)
+    assistant_messages = page.locator(SEL["message_assistant"])
+    chat_input = page.locator(SEL["chat_input"])
+    await chat_input.wait_for(state="visible", timeout=5000)
 
-    # Wait for approval card to be visible (thread is now in AwaitingApproval state)
-    card = page.locator('.approval-card[data-request-id="test-req-waiting-approval"]')
-    await card.wait_for(state="visible", timeout=5000)
+    # Trigger a real HTTP tool call that pauses for approval in the default E2E harness.
+    await chat_input.fill("make approval post approval-required")
+    await chat_input.press("Enter")
 
-    # Record initial message count
-    initial_count = await page.locator(SEL["message_assistant"]).count()
+    card = page.locator(SEL["approval_card"]).last
+    await card.wait_for(state="visible", timeout=10000)
 
-    # Now attempt to send input while approval is pending
-    # (the backend will reject this and return the "Waiting for approval" status message)
-    chat_input = page.locator(SEL["chat_input"])
-    await chat_input.fill("Test input while awaiting approval")
+    tool_name = await card.locator(".approval-tool-name").text_content()
+    desc_text = await card.locator(".approval-description").text_content()
+    assert tool_name == "http"
+    assert desc_text is not None and "HTTP requests to external APIs" in desc_text
+
+    # With the thread now genuinely awaiting approval, the next message should be rejected
+    # as a non-error pending status.
+    initial_count = await assistant_messages.count()
+    await chat_input.fill("send another message now")
     await chat_input.press("Enter")
 
-    # Wait for the status message from the backend rejection
     await page.wait_for_function(
         f"() => document.querySelectorAll('{SEL['message_assistant']}').length > {initial_count}",
         timeout=10000,
     )
 
-    # Get the new status message
-    last_msg = page.locator(SEL["message_assistant"]).last
-    msg_text = await last_msg.text_content()
+    last_msg = assistant_messages.last.locator(".message-content")
+    msg_text = await last_msg.inner_text()
 
     # Verify no "Error:" prefix
     assert not msg_text.lower().startswith("error:"), (
@@ -183,9 +180,9 @@ async def test_waiting_for_approval_message_no_error_prefix(page):
     )
 
     # Verify it contains the tool name and description
-    assert "shell" in msg_text.lower(), (
-        f"Expected tool name 'shell' in message. Got: {msg_text!r}"
+    assert "http" in msg_text.lower(), (
+        f"Expected tool name 'http' in message. Got: {msg_text!r}"
     )
-    assert "echo hello" in msg_text, (
+    assert "HTTP requests to external APIs" in msg_text, (
         f"Expected tool description in message. Got: {msg_text!r}"
     )
diff --git a/tests/e2e_advanced_traces.rs b/tests/e2e_advanced_traces.rs
index 0182d99950..cd273d10ef 100644
--- a/tests/e2e_advanced_traces.rs
+++ b/tests/e2e_advanced_traces.rs
@@ -442,6 +442,9 @@ mod advanced {
             other => panic!("expected event trigger, got {other:?}"),
         }
 
+        rig.clear().await;
+        let llm_calls_before = rig.llm_call_count();
+
         rig.send_incoming(IncomingMessage::new(
             "telegram",
             "test-user",
@@ -451,8 +454,18 @@ mod advanced {
 
         let runs = wait_for_routine_run(rig.database(), routine.id, TIMEOUT).await;
         assert_eq!(runs[0].trigger_type, "event");
+        assert_eq!(
+            rig.llm_call_count(),
+            llm_calls_before + 1,
+            "matching event message should only trigger the routine LLM call"
+        );
 
-        let responses = rig.wait_for_responses(3, TIMEOUT).await;
+        let responses = rig.wait_for_responses(1, TIMEOUT).await;
+        assert_eq!(
+            responses.len(),
+            1,
+            "expected only the routine notification after the matching event"
+        );
         assert!(
             responses.iter().any(|response| {
                 response
@@ -505,6 +518,9 @@ mod advanced {
             other => panic!("expected event trigger, got {other:?}"),
         }
 
+        rig.clear().await;
+        let llm_calls_before = rig.llm_call_count();
+
         rig.send_incoming(IncomingMessage::new(
             "telegram",
             "test-user",
@@ -514,6 +530,22 @@ mod advanced {
 
         let runs = wait_for_routine_run(rig.database(), routine.id, TIMEOUT).await;
         assert_eq!(runs[0].trigger_type, "event");
+        assert_eq!(
+            rig.llm_call_count(),
+            llm_calls_before + 1,
+            "matching event message should only trigger the routine LLM call"
+        );
+
+        let responses = rig.wait_for_responses(1, TIMEOUT).await;
+        assert_eq!(
+            responses.len(),
+            1,
+            "expected only the routine notification after the matching event"
+        );
+        assert!(
+            responses[0].content.contains("Bug report detected"),
+            "expected routine notification, got: {responses:?}"
+        );
 
         rig.shutdown();
     }
diff --git a/tests/e2e_telegram_message_routing.rs b/tests/e2e_telegram_message_routing.rs
new file mode 100644
index 0000000000..cad2387ca0
--- /dev/null
+++ b/tests/e2e_telegram_message_routing.rs
@@ -0,0 +1,353 @@
+//! E2E tests for Telegram message routing through the real agent + message tool.
+
+#[cfg(feature = "libsql")]
+mod support;
+
+#[cfg(feature = "libsql")]
+mod tests {
+    use std::sync::Arc;
+    use std::time::Duration;
+
+    use async_trait::async_trait;
+    use futures::StreamExt;
+    use ironclaw::agent::{Agent, AgentDeps};
+    use ironclaw::app::{AppBuilder, AppBuilderFlags};
+    use ironclaw::channels::web::log_layer::LogBroadcaster;
+    use ironclaw::channels::{
+        Channel, ChannelManager, IncomingMessage, MessageStream, OutgoingResponse, StatusUpdate,
+    };
+    use ironclaw::config::Config;
+    use ironclaw::db::{Database, libsql::LibSqlBackend};
+    use ironclaw::error::ChannelError;
+    use ironclaw::llm::{LlmProvider, SessionConfig, SessionManager};
+    use tokio::sync::{Mutex, mpsc};
+    use tokio_stream::wrappers::ReceiverStream;
+
+    use crate::support::test_channel::{TestChannel, TestChannelHandle};
+    use crate::support::trace_llm::{LlmTrace, TraceLlm, TraceResponse, TraceStep, TraceToolCall};
+
+    type TelegramCaptures = Arc<Mutex<Vec<(String, OutgoingResponse)>>>;
+
+    struct RecordingTelegramChannel {
+        captures: TelegramCaptures,
+    }
+
+    impl RecordingTelegramChannel {
+        fn new() -> (Self, TelegramCaptures) {
+            let captures = Arc::new(Mutex::new(Vec::new()));
+            (
+                Self {
+                    captures: Arc::clone(&captures),
+                },
+                captures,
+            )
+        }
+    }
+
+    #[async_trait]
+    impl Channel for RecordingTelegramChannel {
+        fn name(&self) -> &str {
+            "telegram"
+        }
+
+        async fn start(&self) -> Result<MessageStream, ChannelError> {
+            let (_tx, rx) = mpsc::channel::<IncomingMessage>(1);
+            Ok(ReceiverStream::new(rx).boxed())
+        }
+
+        async fn respond(
+            &self,
+            _msg: &IncomingMessage,
+            response: OutgoingResponse,
+        ) -> Result<(), ChannelError> {
+            self.captures
+                .lock()
+                .await
+                .push(("respond".to_string(), response));
+            Ok(())
+        }
+
+        async fn send_status(
+            &self,
+            _status: StatusUpdate,
+            _metadata: &serde_json::Value,
+        ) -> Result<(), ChannelError> {
+            Ok(())
+        }
+
+        async fn broadcast(
+            &self,
+            user_id: &str,
+            response: OutgoingResponse,
+        ) -> Result<(), ChannelError> {
+            self.captures
+                .lock()
+                .await
+                .push((user_id.to_string(), response));
+            Ok(())
+        }
+
+        async fn health_check(&self) -> Result<(), ChannelError> {
+            Ok(())
+        }
+    }
+
+    struct Harness {
+        gateway: Arc<TestChannel>,
+        telegram_captures: Arc<Mutex<Vec<(String, OutgoingResponse)>>>,
+        db: Arc<dyn Database>,
+        owner_id: String,
+        _temp_dir: tempfile::TempDir,
+        agent_handle: Option<tokio::task::JoinHandle<()>>,
+    }
+
+    impl Harness {
+        async fn store_telegram_owner_binding(&self, owner_id: i64) {
+            for scope in [&self.owner_id, "test-user"] {
+                self.db
+                    .set_setting(
+                        scope,
+                        "channels.wasm_channel_owner_ids.telegram",
+                        &serde_json::json!(owner_id),
+                    )
+                    .await
+                    .expect("failed to store telegram owner binding");
+            }
+        }
+
+        async fn wait_for_telegram_broadcasts(
+            &self,
+            expected: usize,
+            timeout: Duration,
+        ) -> Vec<(String, OutgoingResponse)> {
+            let deadline = tokio::time::Instant::now() + timeout;
+            loop {
+                let snapshot = self.telegram_captures.lock().await.clone();
+                if snapshot.len() >= expected || tokio::time::Instant::now() >= deadline {
+                    return snapshot;
+                }
+                tokio::time::sleep(Duration::from_millis(50)).await;
+            }
+        }
+    }
+
+    impl Drop for Harness {
+        fn drop(&mut self) {
+            self.gateway.signal_shutdown();
+            if let Some(handle) = self.agent_handle.take() {
+                handle.abort();
+            }
+        }
+    }
+
+    async fn build_harness(trace: LlmTrace) -> Harness {
+        let temp_dir = tempfile::tempdir().expect("failed to create temp dir");
+        let db_path = temp_dir.path().join("telegram_message_routing.db");
+        let backend = LibSqlBackend::new_local(&db_path)
+            .await
+            .expect("failed to create test LibSqlBackend");
+        backend
+            .run_migrations()
+            .await
+            .expect("failed to run migrations");
+        let db: Arc<dyn Database> = Arc::new(backend);
+
+        let skills_dir = temp_dir.path().join("skills");
+        let installed_skills_dir = temp_dir.path().join("installed_skills");
+        let _ = std::fs::create_dir_all(&skills_dir);
+        let _ = std::fs::create_dir_all(&installed_skills_dir);
+        let mut config = Config::for_testing(db_path, skills_dir, installed_skills_dir);
+        config.agent.auto_approve_tools = true;
+
+        let session = Arc::new(SessionManager::new(SessionConfig::default()));
+        let log_broadcaster = Arc::new(LogBroadcaster::new());
+        let llm: Arc<dyn LlmProvider> = Arc::new(TraceLlm::from_trace(trace));
+
+        let mut builder = AppBuilder::new(
+            config,
+            AppBuilderFlags::default(),
+            None,
+            session,
+            log_broadcaster,
+        );
+        builder.with_database(Arc::clone(&db));
+        builder.with_llm(llm);
+
+        let mut components = builder
+            .build_all()
+            .await
+            .expect("AppBuilder::build_all() failed");
+        components.config.agent.auto_approve_tools = true;
+        components.config.agent.allow_local_tools = true;
+
+        let deps = AgentDeps {
+            owner_id: components.config.owner_id.clone(),
+            store: components.db.clone(),
+            llm: components.llm.clone(),
+            cheap_llm: components.cheap_llm.clone(),
+            safety: components.safety.clone(),
+            tools: components.tools.clone(),
+            workspace: components.workspace.clone(),
+            extension_manager: components.extension_manager.clone(),
+            skill_registry: components.skill_registry.clone(),
+            skill_catalog: components.skill_catalog.clone(),
+            skills_config: components.config.skills.clone(),
+            hooks: components.hooks.clone(),
+            cost_guard: components.cost_guard.clone(),
+            sse_tx: None,
+            http_interceptor: None,
+            transcription: None,
+            document_extraction: None,
+        };
+
+        let gateway = Arc::new(TestChannel::new());
+        let gateway_handle = TestChannelHandle::new(Arc::clone(&gateway));
+        let (telegram_channel, telegram_captures) = RecordingTelegramChannel::new();
+
+        let channel_manager = ChannelManager::new();
+        channel_manager.add(Box::new(gateway_handle)).await;
+        channel_manager.add(Box::new(telegram_channel)).await;
+        let channels = Arc::new(channel_manager);
+
+        deps.tools
+            .register_message_tools(Arc::clone(&channels), deps.extension_manager.clone())
+            .await;
+
+        let agent = Agent::new(
+            components.config.agent.clone(),
+            deps,
+            channels,
+            None,
+            None,
+            None,
+            Some(Arc::clone(&components.context_manager)),
+            None,
+        );
+
+        let agent_handle = tokio::spawn(async move {
+            if let Err(err) = agent.run().await {
+                eprintln!("[telegram routing e2e] Agent exited with error: {err}");
+            }
+        });
+
+        if let Some(rx) = gateway.take_ready_rx().await {
+            let _ = tokio::time::timeout(Duration::from_secs(5), rx).await;
+        }
+
+        Harness {
+            gateway,
+            telegram_captures,
+            db,
+            owner_id: components.config.owner_id.clone(),
+            _temp_dir: temp_dir,
+            agent_handle: Some(agent_handle),
+        }
+    }
+
+    fn single_message_trace(arguments: serde_json::Value, final_text: &str) -> LlmTrace {
+        LlmTrace::single_turn(
+            "telegram-message-routing",
+            "send a reminder",
+            vec![
+                TraceStep {
+                    request_hint: None,
+                    response: TraceResponse::ToolCalls {
+                        tool_calls: vec![TraceToolCall {
+                            id: "call_message_1".to_string(),
+                            name: "message".to_string(),
+                            arguments,
+                        }],
+                        input_tokens: 32,
+                        output_tokens: 12,
+                    },
+                    expected_tool_results: Vec::new(),
+                },
+                TraceStep {
+                    request_hint: None,
+                    response: TraceResponse::Text {
+                        content: final_text.to_string(),
+                        input_tokens: 24,
+                        output_tokens: 8,
+                    },
+                    expected_tool_results: Vec::new(),
+                },
+            ],
+        )
+    }
+
+    #[tokio::test]
+    async fn telegram_message_tool_uses_bound_owner_target_when_target_omitted() {
+        let harness = build_harness(single_message_trace(
+            serde_json::json!({
+                "content": "Walk Conan",
+                "channel": "telegram",
+            }),
+            "Sent on Telegram.",
+        ))
+        .await;
+
+        harness.store_telegram_owner_binding(424242).await;
+
+        harness
+            .gateway
+            .send_message("remind me to walk conan")
+            .await;
+        let responses = harness
+            .gateway
+            .wait_for_responses(1, Duration::from_secs(10))
+            .await;
+        assert!(
+            responses
+                .iter()
+                .any(|response| response.content.contains("Sent on Telegram")),
+            "expected assistant confirmation, got: {:?}",
+            responses
+                .iter()
+                .map(|response| &response.content)
+                .collect::<Vec<_>>()
+        );
+
+        let broadcasts = harness
+            .wait_for_telegram_broadcasts(1, Duration::from_secs(10))
+            .await;
+        assert_eq!(
+            broadcasts.len(),
+            1,
+            "expected exactly one telegram broadcast"
+        );
+        assert_eq!(broadcasts[0].0, "424242");
+        assert_eq!(broadcasts[0].1.content, "Walk Conan");
+    }
+
+    #[tokio::test]
+    async fn telegram_message_tool_prefers_explicit_target_over_bound_owner_target() {
+        let harness = build_harness(single_message_trace(
+            serde_json::json!({
+                "content": "Walk Conan",
+                "channel": "telegram",
+                "target": "999999",
+            }),
+            "Sent on Telegram.",
+        ))
+        .await;
+
+        harness.store_telegram_owner_binding(424242).await;
+
+        harness.gateway.send_message("send the reminder").await;
+        let _ = harness
+            .gateway
+            .wait_for_responses(1, Duration::from_secs(10))
+            .await;
+
+        let broadcasts = harness
+            .wait_for_telegram_broadcasts(1, Duration::from_secs(10))
+            .await;
+        assert_eq!(
+            broadcasts.len(),
+            1,
+            "expected exactly one telegram broadcast"
+        );
+        assert_eq!(broadcasts[0].0, "999999");
+        assert_eq!(broadcasts[0].1.content, "Walk Conan");
+    }
+}
diff --git a/tests/fixtures/llm_traces/advanced/routine_event_any_channel.json b/tests/fixtures/llm_traces/advanced/routine_event_any_channel.json
index 6ff2ec54dd..61edf1e2a1 100644
--- a/tests/fixtures/llm_traces/advanced/routine_event_any_channel.json
+++ b/tests/fixtures/llm_traces/advanced/routine_event_any_channel.json
@@ -34,14 +34,6 @@
         "output_tokens": 18
       }
     },
-    {
-      "response": {
-        "type": "text",
-        "content": "I saw the Telegram message.",
-        "input_tokens": 90,
-        "output_tokens": 12
-      }
-    },
     {
       "response": {
         "type": "text",
diff --git a/tests/fixtures/llm_traces/advanced/routine_event_telegram.json b/tests/fixtures/llm_traces/advanced/routine_event_telegram.json
index afa38062f2..b17c538287 100644
--- a/tests/fixtures/llm_traces/advanced/routine_event_telegram.json
+++ b/tests/fixtures/llm_traces/advanced/routine_event_telegram.json
@@ -35,14 +35,6 @@
         "output_tokens": 20
       }
     },
-    {
-      "response": {
-        "type": "text",
-        "content": "I saw the Telegram message.",
-        "input_tokens": 90,
-        "output_tokens": 12
-      }
-    },
     {
       "response": {
         "type": "text",
diff --git a/tests/support/test_rig.rs b/tests/support/test_rig.rs
index 8549a21cb1..8d41a26119 100644
--- a/tests/support/test_rig.rs
+++ b/tests/support/test_rig.rs
@@ -653,7 +653,7 @@ impl TestRigBuilder {
 
         // 7b. Register message tool so routines can send messages to channels.
         deps.tools
-            .register_message_tools(Arc::clone(&channels))
+            .register_message_tools(Arc::clone(&channels), deps.extension_manager.clone())
             .await;
 
         // 8. Create Agent.