diff --git a/server/__tests__/chat.test.ts b/server/__tests__/chat.test.ts
index c561c5aa..66e7739d 100644
--- a/server/__tests__/chat.test.ts
+++ b/server/__tests__/chat.test.ts
@@ -824,3 +824,46 @@ describe('agent definition wiring', () => {
     expect(['contexgin', 'local', 'fallback']).toContain(session.agentDefinitionSource);
   });
 });
+
+describe('closeout prompts echo to frontend', () => {
+  let chatSource: string;
+
+  beforeAll(async () => {
+    const { readFileSync } = await import('fs');
+    const { join } = await import('path');
+    chatSource = readFileSync(join(import.meta.dirname, '..', 'chat.ts'), 'utf-8');
+  });
+
+  it('echoCloseoutPrompt helper calls storeAndEchoIfNew', () => {
+    const fnStart = chatSource.indexOf('function echoCloseoutPrompt(');
+    expect(fnStart).toBeGreaterThan(-1);
+    const fnEnd = chatSource.indexOf('\n}', fnStart);
+    const fnBody = chatSource.slice(fnStart, fnEnd);
+    expect(fnBody).toContain('storeAndEchoIfNew(');
+    expect(fnBody).toContain("log.debug('skipping closeout echo");
+  });
+
+  it('auto-closeout calls echoCloseoutPrompt before inputQueue.push', () => {
+    const fnStart = chatSource.indexOf('function _closeoutSessionInner(');
+    expect(fnStart).toBeGreaterThan(-1);
+    const fnEnd = chatSource.indexOf('\n}', fnStart);
+    const fnBody = chatSource.slice(fnStart, fnEnd);
+    const echoIdx = fnBody.indexOf('echoCloseoutPrompt(');
+    const pushIdx = fnBody.indexOf('session.inputQueue.push(');
+    expect(echoIdx).toBeGreaterThan(-1);
+    expect(pushIdx).toBeGreaterThan(-1);
+    expect(echoIdx).toBeLessThan(pushIdx);
+  });
+
+  it('user-closeout calls echoCloseoutPrompt before inputQueue.push', () => {
+    const fnStart = chatSource.indexOf('export function closeSessionByUser(');
+    expect(fnStart).toBeGreaterThan(-1);
+    const fnEnd = chatSource.indexOf('\nexport function', fnStart + 1);
+    const fnBody = chatSource.slice(fnStart, fnEnd > -1 ? fnEnd : undefined);
+    const echoIdx = fnBody.indexOf('echoCloseoutPrompt(');
+    const pushIdx = fnBody.indexOf('session.inputQueue.push(');
+    expect(echoIdx).toBeGreaterThan(-1);
+    expect(pushIdx).toBeGreaterThan(-1);
+    expect(echoIdx).toBeLessThan(pushIdx);
+  });
+});
diff --git a/server/chat.ts b/server/chat.ts
index c30bee3b..50579b77 100644
--- a/server/chat.ts
+++ b/server/chat.ts
@@ -1355,6 +1355,27 @@ export function cleanupSessionWorktrees(
   if (primary) session.worktreePaths.set('primary', primary);
 }
 
+/** Echo a closeout prompt to the frontend as a user bubble before injecting into the SDK. */
+function echoCloseoutPrompt(
+  session: import('./session-registry.js').ManagedSession,
+  clientId: string,
+  prompt: string,
+): void {
+  const messageId = `umsg-${Date.now()}-${randomUUID().slice(0, 8)}-closeout`;
+  if (session.sessionId) {
+    storeAndEchoIfNew(
+      session.sessionId,
+      messageId,
+      prompt,
+      clientId,
+      session.transport,
+      session.observers,
+    );
+  } else {
+    log.debug('skipping closeout echo — session not yet resolved', { clientId });
+  }
+}
+
 const CLOSEOUT_PROMPT = `This session is closing in 10 minutes due to inactivity.
 Please perform session closeout:
 
@@ -1410,7 +1431,7 @@ function _closeoutSessionInner(clientId: string): void {
 
   log.info('injecting closeout prompt', { clientId, wtId: session.wtId });
 
-  // Push the closeout prompt as an interrupt so the agent sees it immediately
+  echoCloseoutPrompt(session, clientId, CLOSEOUT_PROMPT);
   session.inputQueue.push(makeUserMessage(CLOSEOUT_PROMPT, 'now'));
 
   // The registry's CLOSEOUT_TIMEOUT_MS timer will abort the session after
@@ -1495,7 +1516,7 @@ export function closeSessionByUser(clientId: string): void {
 
     log.info('user-initiated closeout', { clientId, wtId: session.wtId });
 
-    // Inject closeout prompt
+    echoCloseoutPrompt(session, clientId, USER_CLOSEOUT_PROMPT);
     session.inputQueue.push(makeUserMessage(USER_CLOSEOUT_PROMPT, 'now'));
 
     // Register abort listener to finalize with closed_by: 'user'