diff --git a/src/server/__tests__/conversations.test.ts b/src/server/__tests__/conversations.test.ts
index 58a5bf4d..2d6dc7e7 100644
--- a/src/server/__tests__/conversations.test.ts
+++ b/src/server/__tests__/conversations.test.ts
@@ -235,6 +235,29 @@ describe('WebSocket Chat Integration', () => {
     }
   }
 
+  async function withMockExitAfterFirstUser<T>(
+    delayMs: number | undefined,
+    callback: () => Promise<T>,
+  ): Promise<T> {
+    const previousDelay = process.env.MOCK_SDK_EXIT_AFTER_FIRST_USER_MS
+
+    if (delayMs && delayMs > 0) {
+      process.env.MOCK_SDK_EXIT_AFTER_FIRST_USER_MS = String(delayMs)
+    } else {
+      delete process.env.MOCK_SDK_EXIT_AFTER_FIRST_USER_MS
+    }
+
+    try {
+      return await callback()
+    } finally {
+      if (previousDelay === undefined) {
+        delete process.env.MOCK_SDK_EXIT_AFTER_FIRST_USER_MS
+      } else {
+        process.env.MOCK_SDK_EXIT_AFTER_FIRST_USER_MS = previousDelay
+      }
+    }
+  }
+
   async function runTurn(sessionId: string, content: string, allowError = false): Promise<any[]> {
     const messages: any[] = []
     const ws = new WebSocket(`${wsUrl}/ws/${sessionId}`)
@@ -277,6 +300,39 @@ describe('WebSocket Chat Integration', () => {
     return messages
   }
 
+  async function runTurnUntilComplete(sessionId: string, content: string): Promise<any[]> {
+    const messages: any[] = []
+    const ws = new WebSocket(`${wsUrl}/ws/${sessionId}`)
+
+    await new Promise<void>((resolve, reject) => {
+      const timeout = setTimeout(() => {
+        ws.close()
+        reject(new Error(`Timed out waiting for terminal event for session ${sessionId}`))
+      }, 10000)
+
+      ws.onmessage = (e) => {
+        const msg = JSON.parse(e.data as string)
+        messages.push(msg)
+        if (msg.type === 'connected') {
+          ws.send(JSON.stringify({ type: 'user_message', content }))
+        }
+        if (msg.type === 'message_complete') {
+          clearTimeout(timeout)
+          ws.close()
+          resolve()
+        }
+      }
+
+      ws.onerror = () => {
+        clearTimeout(timeout)
+        ws.close()
+        reject(new Error(`WebSocket error for session ${sessionId}`))
+      }
+    })
+
+    return messages
+  }
+
   async function waitUntil(
     predicate: () => boolean | Promise<boolean>,
     label: string,
@@ -434,6 +490,24 @@ describe('WebSocket Chat Integration', () => {
     ).toBe(true)
   })
 
+  it('should complete the client turn when the CLI exits after startup', async () => {
+    const messages = await withMockExitAfterFirstUser(50, () =>
+      runTurnUntilComplete(`chat-late-exit-${crypto.randomUUID()}`, 'trigger late exit'),
+    )
+
+    expect(
+      messages.some(
+        (m) =>
+          m.type === 'error' &&
+          m.code === 'CLI_ERROR' &&
+          typeof m.message === 'string' &&
+          m.message.includes('CLI process exited unexpectedly'),
+      ),
+    ).toBe(true)
+    expect(messages.some((m) => m.type === 'message_complete')).toBe(true)
+    expect(messages.at(-1)?.type).toBe('message_complete')
+  }, 15_000)
+
   it('should handle permission_response without error', async () => {
     const messages: any[] = []
     const ws = new WebSocket(`${wsUrl}/ws/chat-test-4`)
diff --git a/src/server/__tests__/fixtures/mock-sdk-cli.ts b/src/server/__tests__/fixtures/mock-sdk-cli.ts
index b0e624c3..20ebcabd 100644
--- a/src/server/__tests__/fixtures/mock-sdk-cli.ts
+++ b/src/server/__tests__/fixtures/mock-sdk-cli.ts
@@ -26,7 +26,10 @@ const sdkUrl = getArg('--sdk-url')
 const sessionId = getArg('--session-id') || crypto.randomUUID()
 const initMode = process.env.MOCK_SDK_INIT_MODE || 'on_open'
 const streamDelayMs = Number(process.env.MOCK_SDK_STREAM_DELAY_MS || '0')
+const exitAfterOpenMs = Number(process.env.MOCK_SDK_EXIT_AFTER_OPEN_MS || '0')
+const exitAfterFirstUserMs = Number(process.env.MOCK_SDK_EXIT_AFTER_FIRST_USER_MS || '0')
 let initSent = false
+let firstUserExitScheduled = false
 
 if (!sdkUrl) {
   console.error('Missing --sdk-url')
@@ -51,6 +54,9 @@ ws.addEventListener('open', () => {
   if (initMode !== 'on_first_user') {
     sendInit()
   }
+  if (exitAfterOpenMs > 0) {
+    setTimeout(() => process.exit(1), exitAfterOpenMs)
+  }
 })
 
 ws.addEventListener('message', (event) => {
@@ -63,6 +69,11 @@ ws.addEventListener('message', (event) => {
 
       if (parsed.type === 'user') {
         sendInit()
+        if (exitAfterFirstUserMs > 0 && !firstUserExitScheduled) {
+          firstUserExitScheduled = true
+          setTimeout(() => process.exit(1), exitAfterFirstUserMs)
+          continue
+        }
         const text = extractUserText(parsed)
         emit(ws, {
           type: 'stream_event',
diff --git a/src/server/services/conversationService.ts b/src/server/services/conversationService.ts
index 0db3170d..127d5532 100644
--- a/src/server/services/conversationService.ts
+++ b/src/server/services/conversationService.ts
@@ -477,6 +477,17 @@ export class ConversationService {
 
     const activeSession = this.sessions.get(sessionId)
     if (activeSession?.proc === proc) {
+      const exitError = this.buildRuntimeExitMessage(sessionId, code)
+      for (const cb of activeSession.outputCallbacks) {
+        cb({
+          type: 'result',
+          subtype: 'error',
+          is_error: true,
+          result: exitError,
+          usage: { input_tokens: 0, output_tokens: 0 },
+          session_id: sessionId,
+        })
+      }
       this.sessions.delete(sessionId)
     }
   }
@@ -783,6 +794,26 @@ export class ConversationService {
     )
   }
 
+  private buildRuntimeExitMessage(sessionId: string, exitCode: number): string {
+    const session = this.sessions.get(sessionId)
+    const stderrText = session?.stderrLines.join('\n').trim() ?? ''
+    const recentMessages = session?.sdkMessages ?? []
+    const resultMessage = [...recentMessages]
+      .reverse()
+      .find((msg) => msg?.type === 'result' && msg.is_error)
+    const authStatus = [...recentMessages]
+      .reverse()
+      .find((msg) => msg?.type === 'auth_status')
+    const detail =
+      this.extractStartupDetail(resultMessage) ||
+      this.extractStartupDetail(authStatus) ||
+      stderrText
+
+    return detail
+      ? `CLI process exited unexpectedly (code ${exitCode}): ${detail}`
+      : `CLI process exited unexpectedly with code ${exitCode}.`
+  }
+
   private extractStartupDetail(message: any): string {
     if (!message) return ''