diff --git a/src/__tests__/mcp-server.test.ts b/src/__tests__/mcp-server.test.ts
index cfec208b..021c1497 100644
--- a/src/__tests__/mcp-server.test.ts
+++ b/src/__tests__/mcp-server.test.ts
@@ -659,6 +659,42 @@ describe('MCP Tool Handlers', () => {
     expect(result.content[0].text).toContain('Session not found');
   });
 
+  it('get_status handler includes pendingQuestion when session is ask_question', async () => {
+    let callCount = 0;
+    const ts = Date.now();
+    (fetch as any).mockImplementation(() => {
+      callCount++;
+      if (callCount === 1) {
+        return {
+          ok: true,
+          json: () => Promise.resolve({
+            id: UUID,
+            status: 'ask_question',
+            pendingQuestion: {
+              toolUseId: 'toolu_abc123',
+              content: 'Which strategy? 1) Clean up 2) Auto-restart 3) Both',
+              options: ['Clean up', 'Auto-restart', 'Both'],
+              since: ts,
+            },
+          }),
+        };
+      }
+      return { ok: true, json: () => Promise.resolve({ alive: true, status: 'ask_question' }) };
+    });
+
+    const handler = getToolHandler('get_status');
+    const result = await handler({ sessionId: UUID });
+    expect(result.isError).toBeFalsy();
+    const data = parseResult(result);
+    expect(data.status).toBe('ask_question');
+    expect(data.pendingQuestion).toEqual({
+      toolUseId: 'toolu_abc123',
+      content: 'Which strategy? 1) Clean up 2) Auto-restart 3) Both',
+      options: ['Clean up', 'Auto-restart', 'Both'],
+      since: ts,
+    });
+  });
+
   // ── get_transcript handler ──
 
   it('get_transcript handler returns transcript', async () => {
diff --git a/src/server.ts b/src/server.ts
index dd0e3c9d..aeed354b 100644
--- a/src/server.ts
+++ b/src/server.ts
@@ -577,12 +577,12 @@ app.post('/sessions', async (req, reply) => {
 app.get<{ Params: { id: string } }>('/v1/sessions/:id', async (req, reply) => {
   const session = sessions.getSession(req.params.id);
   if (!session) return reply.status(404).send({ error: 'Session not found' });
-  return addActionHints(session);
+  return addActionHints(session, sessions);
 });
 app.get<{ Params: { id: string } }>('/sessions/:id', async (req, reply) => {
   const session = sessions.getSession(req.params.id);
   if (!session) return reply.status(404).send({ error: 'Session not found' });
-  return addActionHints(session);
+  return addActionHints(session, sessions);
 });
 
 // #128: Bulk health check — returns health for all sessions in one request
@@ -1276,7 +1276,10 @@ async function reapZombieSessions(): Promise<void> {
 // ── Helpers ──────────────────────────────────────────────────────────
 
 /** Issue #20: Add actionHints to session response for interactive states. */
-function addActionHints(session: import('./session.js').SessionInfo): Record<string, unknown> {
+function addActionHints(
+  session: import('./session.js').SessionInfo,
+  sessions?: SessionManager,
+): Record<string, unknown> {
   // #357: Convert Set to array for JSON serialization
   const result: Record<string, unknown> = {
     ...session,
@@ -1288,9 +1291,34 @@ function addActionHints(session: import('./session.js').SessionInfo): Record<str
       reject: { method: 'POST', url: `/v1/sessions/${session.id}/reject`, description: 'Reject the pending permission' },
     };
   }
+  // #599: Expose pending question data for MCP/REST callers
+  if (session.status === 'ask_question' && sessions) {
+    const info = sessions.getPendingQuestionInfo(session.id);
+    if (info) {
+      result.pendingQuestion = {
+        toolUseId: info.toolUseId,
+        content: info.question,
+        options: extractQuestionOptions(info.question),
+        since: info.timestamp,
+      };
+    }
+  }
   return result;
 }
 
+/** #599: Extract selectable options from AskUserQuestion text. */
+function extractQuestionOptions(text: string): string[] | null {
+  // Numbered options: "1. Foo\n2. Bar"
+  const numberedRegex = /^\s*(\d+)\.\s+(.+)$/gm;
+  const options: string[] = [];
+  let m;
+  while ((m = numberedRegex.exec(text)) !== null) {
+    options.push(m[2].trim());
+  }
+  if (options.length >= 2) return options.slice(0, 4);
+  return null;
+}
+
 function makePayload(
   event: SessionEvent,
   sessionId: string,
diff --git a/src/session.ts b/src/session.ts
index 4b5b06ff..881cc2c3 100644
--- a/src/session.ts
+++ b/src/session.ts
@@ -85,6 +85,7 @@ interface PendingQuestion {
   timer: NodeJS.Timeout;
   toolUseId: string;
   question: string;
+  timestamp: number;
 }
 
 export class SessionManager {
@@ -955,7 +956,7 @@ export class SessionManager {
         resolve(null);
       }, timeoutMs);
 
-      this.pendingQuestions.set(sessionId, { resolve, timer, toolUseId, question });
+      this.pendingQuestions.set(sessionId, { resolve, timer, toolUseId, question, timestamp: Date.now() });
     });
   }
 
@@ -976,9 +977,9 @@ export class SessionManager {
   }
 
   /** Issue #336: Get info about a pending question. */
-  getPendingQuestionInfo(sessionId: string): { toolUseId: string; question: string } | null {
+  getPendingQuestionInfo(sessionId: string): { toolUseId: string; question: string; timestamp: number } | null {
     const pending = this.pendingQuestions.get(sessionId);
-    return pending ? { toolUseId: pending.toolUseId, question: pending.question } : null;
+    return pending ? { toolUseId: pending.toolUseId, question: pending.question, timestamp: pending.timestamp } : null;
   }
 
   /** Issue #336: Clean up any pending question for a session. */