diff --git a/ui/src/components/chat/hooks/useChatComposerState.test.ts b/ui/src/components/chat/hooks/useChatComposerState.test.ts
index 104f5193..b5e1f7a0 100644
--- a/ui/src/components/chat/hooks/useChatComposerState.test.ts
+++ b/ui/src/components/chat/hooks/useChatComposerState.test.ts
@@ -1,5 +1,8 @@
 import { describe, expect, it } from 'vitest';
-import { shouldCycleRunModeOnKeyDown } from './useChatComposerState';
+import {
+  createWebSocketSendFailureMessage,
+  shouldCycleRunModeOnKeyDown,
+} from './useChatComposerState';
 
 function keyEvent(key: string, shiftKey = false) {
   return { key, shiftKey };
@@ -28,3 +31,13 @@ describe('useChatComposerState keyboard shortcuts', () => {
     })).toBe(false);
   });
 });
+
+describe('createWebSocketSendFailureMessage', () => {
+  it('builds a visible error message for failed websocket sends', () => {
+    const message = createWebSocketSendFailureMessage();
+
+    expect(message.type).toBe('error');
+    expect(message.content).toContain('not connected');
+    expect(message.content).toContain('try again');
+  });
+});
diff --git a/ui/src/components/chat/hooks/useChatComposerState.ts b/ui/src/components/chat/hooks/useChatComposerState.ts
index d9ef95fb..8aa93b76 100644
--- a/ui/src/components/chat/hooks/useChatComposerState.ts
+++ b/ui/src/components/chat/hooks/useChatComposerState.ts
@@ -49,7 +49,7 @@ interface UseChatComposerStateArgs {
   isLoading: boolean;
   canAbortSession: boolean;
   tokenBudget: Record<string, unknown> | null;
-  sendMessage: (message: unknown) => void;
+  sendMessage: (message: unknown) => boolean | void;
   sendByCtrlEnter?: boolean;
   onSessionActive?: (sessionId?: string | null) => void;
   onSessionProcessing?: (sessionId?: string | null) => void;
@@ -105,6 +105,8 @@ const createFakeSubmitEvent = () => {
 
 const MAX_ATTACHMENT_SIZE_BYTES = 20 * 1024 * 1024;
 const MAX_ATTACHMENTS = 10;
+const WEBSOCKET_SEND_FAILURE_TEXT =
+  'PilotDeck is not connected. Please wait for the WebSocket connection to reconnect and try again.';
 
 type UploadedAttachmentFile = {
   name: string;
@@ -126,6 +128,14 @@ export function shouldCycleRunModeOnKeyDown(
   return event.key === 'Tab' && event.shiftKey && !showFileDropdown && !showCommandMenu;
 }
 
+export function createWebSocketSendFailureMessage(): ChatMessage {
+  return {
+    type: 'error',
+    content: WEBSOCKET_SEND_FAILURE_TEXT,
+    timestamp: new Date(),
+  };
+}
+
 function buildAttachmentPathNote(files: UploadedAttachmentFile[]): string {
   if (!files.length) {
     return '';
@@ -677,13 +687,6 @@ export function useChatComposerState({
       // arrives with the real id).
       const optimisticSessionId =
         submitTargetSessionId || createTemporarySessionId();
-      if (selectedProject?.name) {
-        onSessionActivityBump?.(
-          selectedProject.name,
-          optimisticSessionId,
-          userVisibleInput,
-        );
-      }
 
       let uploadedImages: unknown[] = [];
       let uploadedFiles: UploadedAttachmentFile[] = [];
@@ -724,26 +727,6 @@ export function useChatComposerState({
       const effectiveSessionId = submitTargetSessionId;
       const sessionToActivate = effectiveSessionId || optimisticSessionId;
 
-      const userMessage: ChatMessage = {
-        type: 'user',
-        content: userVisibleInput,
-        images: uploadedImages as any,
-        attachments: uploadedFiles as any,
-        timestamp: new Date(),
-      };
-
-      addMessage(userMessage, submitTargetSessionId);
-      setIsLoading(true); // Processing banner starts
-      setCanAbortSession(true);
-      setClaudeStatus({
-        text: 'Processing',
-        tokens: 0,
-        can_interrupt: true,
-      });
-
-      setIsUserScrolledUp(false);
-      setTimeout(() => scrollToBottom(), 100);
-
       if (!effectiveSessionId && !submitSelectedSession?.id) {
         if (typeof window !== 'undefined') {
           // Reset stale pending IDs from previous interrupted runs before creating a new one.
@@ -751,10 +734,6 @@ export function useChatComposerState({
         }
         pendingViewSessionRef.current = { sessionId: null, startedAt: Date.now() };
       }
-      onSessionActive?.(sessionToActivate);
-      if (effectiveSessionId && !isTemporarySessionId(effectiveSessionId)) {
-        onSessionProcessing?.(effectiveSessionId);
-      }
 
       // PilotDeck-only: a single localStorage entry (`pilotdeck-settings`)
       // tracks tool consent + skip-permissions for every chat. The legacy
@@ -780,7 +759,7 @@ export function useChatComposerState({
       const toolsSettings = getToolsSettings();
       const sessionSummary = getNotificationSessionSummary(submitSelectedSession, userVisibleInput);
 
-      startSessionCommand({
+      const launchResult = startSessionCommand({
         sendMessage,
         selectedProject,
         command: messageContent,
@@ -793,6 +772,49 @@ export function useChatComposerState({
         images: uploadedImages,
       });
 
+      if (!launchResult.sent) {
+        pendingViewSessionRef.current = null;
+        setIsLoading(false);
+        setCanAbortSession(false);
+        setClaudeStatus(null);
+        setPilotDeckStatus(null);
+        addMessage(createWebSocketSendFailureMessage(), submitTargetSessionId);
+        return;
+      }
+
+      if (selectedProject?.name) {
+        onSessionActivityBump?.(
+          selectedProject.name,
+          launchResult.sessionId,
+          userVisibleInput,
+        );
+      }
+
+      const userMessage: ChatMessage = {
+        type: 'user',
+        content: userVisibleInput,
+        images: uploadedImages as any,
+        attachments: uploadedFiles as any,
+        timestamp: new Date(),
+      };
+
+      addMessage(userMessage, submitTargetSessionId);
+      setIsLoading(true); // Processing banner starts
+      setCanAbortSession(true);
+      setClaudeStatus({
+        text: 'Processing',
+        tokens: 0,
+        can_interrupt: true,
+      });
+
+      setIsUserScrolledUp(false);
+      setTimeout(() => scrollToBottom(), 100);
+
+      onSessionActive?.(launchResult.sessionId);
+      if (effectiveSessionId && !isTemporarySessionId(effectiveSessionId)) {
+        onSessionProcessing?.(effectiveSessionId);
+      }
+
       setInput('');
       inputValueRef.current = '';
       resetCommandMenuState();
diff --git a/ui/src/components/chat/utils/sessionLauncher.test.ts b/ui/src/components/chat/utils/sessionLauncher.test.ts
new file mode 100644
index 00000000..5e81314e
--- /dev/null
+++ b/ui/src/components/chat/utils/sessionLauncher.test.ts
@@ -0,0 +1,39 @@
+import { describe, expect, it } from 'vitest';
+import { startSessionCommand } from './sessionLauncher';
+import type { Project } from '../../../types/app';
+
+const project = {
+  name: 'demo',
+  path: '/workspace/demo',
+  fullPath: '/workspace/demo',
+} as Project;
+
+describe('startSessionCommand', () => {
+  it('reports successful websocket sends', () => {
+    const result = startSessionCommand({
+      sendMessage: () => true,
+      selectedProject: project,
+      command: 'hello',
+      temporarySessionId: 'new-session-test',
+    });
+
+    expect(result).toEqual({
+      sessionId: 'new-session-test',
+      sent: true,
+    });
+  });
+
+  it('reports when the websocket command could not be sent', () => {
+    const result = startSessionCommand({
+      sendMessage: () => false,
+      selectedProject: project,
+      command: 'hello',
+      temporarySessionId: 'new-session-test',
+    });
+
+    expect(result).toEqual({
+      sessionId: 'new-session-test',
+      sent: false,
+    });
+  });
+});
diff --git a/ui/src/components/chat/utils/sessionLauncher.ts b/ui/src/components/chat/utils/sessionLauncher.ts
index 763b1b62..f432769e 100644
--- a/ui/src/components/chat/utils/sessionLauncher.ts
+++ b/ui/src/components/chat/utils/sessionLauncher.ts
@@ -3,7 +3,7 @@ import type { ChatAttachment, PilotDeckSettings, PermissionMode } from '../types
 import { getPilotDeckSettings, safeLocalStorage } from './chatStorage';
 
 type StartSessionOptions = {
-  sendMessage: (message: unknown) => void;
+  sendMessage: (message: unknown) => boolean | void;
   selectedProject: Project;
   command: string;
   sessionId?: string | null;
@@ -19,6 +19,11 @@ type StartSessionOptions = {
   workspaceCwd?: string;
 };
 
+type StartSessionResult = {
+  sessionId: string;
+  sent: boolean;
+};
+
 const VALID_PERMISSION_MODES = new Set<PermissionMode>([
   'default',
   'acceptEdits',
@@ -90,12 +95,12 @@ export function startSessionCommand({
   alwaysOnPlanId,
   alwaysOnExecutionToken,
   workspaceCwd,
-}: StartSessionOptions): string {
+}: StartSessionOptions): StartSessionResult {
   const sessionToActivate =
     sessionId || temporarySessionId || createTemporarySessionId();
   const resolvedProjectPath = getSelectedProjectPath(selectedProject);
 
-  sendMessage({
+  const sent = sendMessage({
     type: 'pilotdeck-command',
     command,
     options: {
@@ -112,7 +117,10 @@ export function startSessionCommand({
       ...(Array.isArray(attachments) && attachments.length > 0 ? { attachments } : {}),
       ...(workspaceCwd ? { workspaceCwd } : {}),
     },
-  });
+  }) !== false;
 
-  return sessionToActivate;
+  return {
+    sessionId: sessionToActivate,
+    sent,
+  };
 }
diff --git a/ui/src/contexts/WebSocketContext.tsx b/ui/src/contexts/WebSocketContext.tsx
index 729b97a5..9a33548a 100644
--- a/ui/src/contexts/WebSocketContext.tsx
+++ b/ui/src/contexts/WebSocketContext.tsx
@@ -6,7 +6,7 @@ type WSSubscriber = (msg: any) => void;
 
 type WebSocketContextType = {
   ws: WebSocket | null;
-  sendMessage: (message: any) => void;
+  sendMessage: (message: any) => boolean;
   latestMessage: any | null;
   isConnected: boolean;
   /**
@@ -140,10 +140,16 @@ const useWebSocketProviderState = (): WebSocketContextType => {
   const sendMessage = useCallback((message: any) => {
     const socket = wsRef.current;
     if (socket && socket.readyState === WebSocket.OPEN) {
-      socket.send(JSON.stringify(message));
-    } else {
-      console.warn('WebSocket not connected');
+      try {
+        socket.send(JSON.stringify(message));
+        return true;
+      } catch (error) {
+        console.error('WebSocket send failed:', error);
+        return false;
+      }
     }
+    console.warn('WebSocket not connected');
+    return false;
   }, []);
 
   const subscribe = useCallback<WebSocketContextType['subscribe']>((handler) => {