diff --git a/src/components/chat/hooks/useChatRealtimeHandlers.ts b/src/components/chat/hooks/useChatRealtimeHandlers.ts
index 5c294efa..9fceecd4 100644
--- a/src/components/chat/hooks/useChatRealtimeHandlers.ts
+++ b/src/components/chat/hooks/useChatRealtimeHandlers.ts
@@ -1,20 +1,29 @@
-import { useEffect } from 'react';
+import { useEffect, useRef } from 'react';
 import type { Dispatch, MutableRefObject, SetStateAction } from 'react';
 
 import type { ServerEvent } from '../../../contexts/WebSocketContext';
 import { showCompletionTitleIndicator } from '../../../utils/pageTitleNotification';
-import { playChatCompletionSound } from '../../../utils/notificationSound';
+import { playChatCompletionSound, playNotificationSound } from '../../../utils/notificationSound';
 import type { MarkSessionIdle, MarkSessionProcessing } from '../../../hooks/useSessionProtection';
 import type { PendingPermissionRequest } from '../types/types';
 import type { ProjectSession, LLMProvider } from '../../../types/app';
 import type { SessionStore, NormalizedMessage } from '../../../stores/useSessionStore';
 
+const isActionablePermissionRequest = (request: { toolName?: unknown } | null | undefined): boolean => {
+  return request?.toolName !== 'ExitPlanMode' && request?.toolName !== 'exit_plan_mode';
+};
+
+const hasActionablePermissionRequests = (requests: Array<{ toolName?: unknown }> | null | undefined): boolean => {
+  return Array.isArray(requests) && requests.some((request) => isActionablePermissionRequest(request));
+};
+
 interface UseChatRealtimeHandlersArgs {
   subscribe: (listener: (event: ServerEvent) => void) => () => void;
   provider: LLMProvider;
   selectedSession: ProjectSession | null;
   currentSessionId: string | null;
   setTokenBudget: (budget: Record<string, unknown> | null) => void;
+  pendingPermissionRequests: PendingPermissionRequest[];
   setPendingPermissionRequests: Dispatch<SetStateAction<PendingPermissionRequest[]>>;
   streamTimerRef: MutableRefObject<number | null>;
   accumulatedStreamRef: MutableRefObject<string>;
@@ -52,6 +61,7 @@ export function useChatRealtimeHandlers({
   selectedSession,
   currentSessionId,
   setTokenBudget,
+  pendingPermissionRequests,
   setPendingPermissionRequests,
   streamTimerRef,
   accumulatedStreamRef,
@@ -62,6 +72,15 @@ export function useChatRealtimeHandlers({
   onWebSocketReconnect,
   sessionStore,
 }: UseChatRealtimeHandlersArgs) {
+  // Keep the latest pending-permission snapshot available to the websocket
+  // listener so back-to-back permission events can dedupe and re-arm the
+  // notification sound before React finishes a rerender.
+  const pendingPermissionRequestsRef = useRef(pendingPermissionRequests);
+
+  useEffect(() => {
+    pendingPermissionRequestsRef.current = pendingPermissionRequests;
+  }, [pendingPermissionRequests]);
+
   useEffect(() => {
     const handleEvent = (msg: ServerEvent) => {
       if (!msg.kind) {
@@ -101,7 +120,16 @@ export function useChatRealtimeHandlers({
 
           const isViewedSession = sid === activeViewSessionId;
           if (isViewedSession && Array.isArray(msg.pendingPermissions)) {
-            setPendingPermissionRequests(msg.pendingPermissions as PendingPermissionRequest[]);
+            const nextPendingPermissionRequests = msg.pendingPermissions as PendingPermissionRequest[];
+            const hadActionablePermissionRequests = hasActionablePermissionRequests(pendingPermissionRequestsRef.current);
+            const hasPendingActionablePermissionRequests = hasActionablePermissionRequests(nextPendingPermissionRequests);
+
+            pendingPermissionRequestsRef.current = nextPendingPermissionRequests;
+            setPendingPermissionRequests(nextPendingPermissionRequests);
+
+            if (hasPendingActionablePermissionRequests && !hadActionablePermissionRequests) {
+              void playNotificationSound();
+            }
           }
           return;
         }
@@ -203,6 +231,7 @@ export function useChatRealtimeHandlers({
           // hides it immediately and atomically.
           onSessionIdle?.(sid);
           if (sid === activeViewSessionId) {
+            pendingPermissionRequestsRef.current = [];
             setPendingPermissionRequests([]);
           }
 
@@ -235,9 +264,9 @@ export function useChatRealtimeHandlers({
         case 'permission_request': {
           if (!msg.requestId) break;
           if (sid === activeViewSessionId) {
-            setPendingPermissionRequests((prev) => {
-              if (prev.some((r: PendingPermissionRequest) => r.requestId === msg.requestId)) return prev;
-              return [...prev, {
+            const previousPendingPermissionRequests = pendingPermissionRequestsRef.current;
+            if (!previousPendingPermissionRequests.some((request) => request.requestId === msg.requestId)) {
+              const nextPendingPermissionRequests = [...previousPendingPermissionRequests, {
                 requestId: msg.requestId as string,
                 toolName: (msg.toolName as string) || 'UnknownTool',
                 input: msg.input,
@@ -245,7 +274,17 @@ export function useChatRealtimeHandlers({
                 sessionId: sid || null,
                 receivedAt: new Date(),
               }];
-            });
+
+              pendingPermissionRequestsRef.current = nextPendingPermissionRequests;
+              setPendingPermissionRequests(nextPendingPermissionRequests);
+
+              if (
+                isActionablePermissionRequest({ toolName: msg.toolName })
+                && !hasActionablePermissionRequests(previousPendingPermissionRequests)
+              ) {
+                void playNotificationSound();
+              }
+            }
           }
           if (sid) {
             onSessionProcessing?.(sid);
@@ -255,7 +294,12 @@ export function useChatRealtimeHandlers({
 
         case 'permission_cancelled': {
           if (msg.requestId && sid === activeViewSessionId) {
-            setPendingPermissionRequests((prev) => prev.filter((r: PendingPermissionRequest) => r.requestId !== msg.requestId));
+            const nextPendingPermissionRequests = pendingPermissionRequestsRef.current.filter(
+              (request: PendingPermissionRequest) => request.requestId !== msg.requestId,
+            );
+
+            pendingPermissionRequestsRef.current = nextPendingPermissionRequests;
+            setPendingPermissionRequests(nextPendingPermissionRequests);
           }
           break;
         }
@@ -286,6 +330,7 @@ export function useChatRealtimeHandlers({
     selectedSession,
     currentSessionId,
     setTokenBudget,
+    pendingPermissionRequests,
     setPendingPermissionRequests,
     streamTimerRef,
     accumulatedStreamRef,
diff --git a/src/components/chat/view/ChatInterface.tsx b/src/components/chat/view/ChatInterface.tsx
index 5efe6af4..15786a41 100644
--- a/src/components/chat/view/ChatInterface.tsx
+++ b/src/components/chat/view/ChatInterface.tsx
@@ -239,6 +239,7 @@ function ChatInterface({
     selectedSession,
     currentSessionId,
     setTokenBudget,
+    pendingPermissionRequests,
     setPendingPermissionRequests,
     streamTimerRef,
     accumulatedStreamRef,
diff --git a/src/i18n/locales/en/settings.json b/src/i18n/locales/en/settings.json
index fbcd797a..89d4e651 100644
--- a/src/i18n/locales/en/settings.json
+++ b/src/i18n/locales/en/settings.json
@@ -114,7 +114,7 @@
     },
     "sound": {
       "title": "Sound",
-      "description": "Play a short tone when a chat run finishes.",
+      "description": "Play a short tone when a chat run finishes or needs tool approval.",
       "enabled": "Enabled",
       "test": "Test sound"
     },
diff --git a/src/utils/notificationSound.ts b/src/utils/notificationSound.ts
index 78af2d99..d28d6659 100644
--- a/src/utils/notificationSound.ts
+++ b/src/utils/notificationSound.ts
@@ -58,7 +58,7 @@ const playTone = (
   oscillator.stop(startsAt + duration + 0.02);
 };
 
-export const playChatCompletionSound = async ({ force = false } = {}): Promise<void> => {
+export const playNotificationSound = async ({ force = false } = {}): Promise<void> => {
   if (!force && !isNotificationSoundEnabled()) {
     return;
   }
@@ -81,3 +81,5 @@ export const playChatCompletionSound = async ({ force = false } = {}): Promise<v
     console.warn('Unable to play notification sound:', error);
   }
 };
+
+export const playChatCompletionSound = (options = {}): Promise<void> => playNotificationSound(options);