diff --git a/bin/atris.js b/bin/atris.js
index d0cdb2747..b062eba3e 100755
--- a/bin/atris.js
+++ b/bin/atris.js
@@ -2395,7 +2395,7 @@ if (command === 'guide') {
   upgradeAtris().then(() => process.exit(0)).catch((err) => { console.error(`\n✗ Error: ${err.message || err}`); process.exit(1); });
 } else if (command === 'chat' && (process.argv[3] === '--personal' || process.argv[3] === '-p')) {
   require('../commands/ask').askAtris(process.argv.slice(4))
-    .then(() => exitAfterStdoutDrain(0))
+    .then((code) => exitAfterStdoutDrain(code || 0))
     .catch((error) => {
       console.error(`✗ Ask failed: ${error.message || error}`);
       process.exit(1);
diff --git a/commands/ask.js b/commands/ask.js
index 7787eb123..010685ddb 100644
--- a/commands/ask.js
+++ b/commands/ask.js
@@ -129,6 +129,7 @@ async function askAtris(args) {
       const body = await sendMessage(token, oneShot);
       spinner.stop();
       await typeOut(stripEvents(body.response) || JSON.stringify(body));
+      if (body.success === false) return 1;
     } catch (err) {
       spinner.stop();
       console.error(`✗ ${err.message}`);
diff --git a/test/personal-chat-failure-status.test.js b/test/personal-chat-failure-status.test.js
new file mode 100644
index 000000000..e42cb7671
--- /dev/null
+++ b/test/personal-chat-failure-status.test.js
@@ -0,0 +1,69 @@
+'use strict';
+const test = require('node:test');
+const assert = require('node:assert/strict');
+const fs = require('node:fs');
+const os = require('node:os');
+const path = require('node:path');
+const http = require('node:http');
+const { spawn } = require('node:child_process');
+
+async function runChat(t, reply, interactive = false) {
+  const dir = fs.mkdtempSync(path.join(os.tmpdir(), 'atris-chat-status-'));
+  t.after(() => fs.rmSync(dir, { recursive: true, force: true }));
+  const requests = [];
+  const server = http.createServer((req, res) => {
+    let body = '';
+    req.on('data', chunk => { body += chunk; });
+    req.on('end', () => {
+      requests.push({ path: req.url, body: JSON.parse(body) });
+      res.writeHead(200, { 'content-type': 'application/json' });
+      res.end(JSON.stringify(reply));
+    });
+  });
+  await new Promise(resolve => server.listen(0, '127.0.0.1', resolve));
+  t.after(() => new Promise(resolve => { server.closeAllConnections(); server.close(resolve); }));
+  const token = `test.${Buffer.from(JSON.stringify({ type: 'agent_access', exp: Math.floor(Date.now() / 1000) + 3600 })).toString('base64url')}.test`;
+  const env = { PATH: process.env.PATH, HOME: dir, TMPDIR: dir, ATRIS_SKIP_UPDATE_CHECK: '1', ATRIS_AGENT_TOKEN_FILE: path.join(dir, 'token.json'), ATRIS_TOKEN: token, ATRIS_API_URL: `http://127.0.0.1:${server.address().port}/api`, NO_COLOR: '1' };
+  const args = [path.resolve(__dirname, '../bin/atris.js'), 'chat', '--personal', ...(interactive ? [] : ['hello'])];
+  const child = spawn(process.execPath, args, { cwd: dir, env, stdio: [interactive ? 'pipe' : 'ignore', 'pipe', 'pipe'] });
+  let stdout = '', stderr = '', sentBye = false;
+  child.stdout.on('data', chunk => {
+    stdout += chunk;
+    if (interactive && !sentBye && stdout.includes('confirm whether it finished')) {
+      sentBye = true;
+      setTimeout(() => child.stdin.end('bye\n'), 50);
+    }
+  });
+  if (interactive) child.stdin.write('hello\n');
+  child.stderr.on('data', chunk => { stderr += chunk; });
+  const timer = setTimeout(() => child.kill('SIGKILL'), 5000);
+  let code;
+  try {
+    code = await new Promise((resolve, reject) => { child.once('error', reject); child.once('close', resolve); });
+  } finally { clearTimeout(timer); }
+  return { code, stdout, stderr, requests };
+}
+
+test('one-shot personal chat prints uncertainty and reports failure', async t => {
+  const result = await runChat(t, { success: false, intent: 'message_received', response: "I received this request, but I can't confirm whether it finished. Check the result before starting it again.", agent_id: 'agent-1' });
+  assert.equal(result.code, 1, result.stderr);
+  assert.match(result.stdout, /can't confirm whether it finished/);
+  assert.deepEqual(result.requests, [{ path: '/api/message/incoming', body: { message: 'hello', source: 'cli' } }]);
+});
+
+test('one-shot personal chat retains success and legacy response handling', async t => {
+  for (const reply of [{ success: true, response: 'All done.' }, { response: 'Older reply.' }]) {
+    const result = await runChat(t, reply);
+    assert.equal(result.code, 0, result.stderr);
+    assert.match(result.stdout, new RegExp(reply.response.replace('.', '\\.')));
+    assert.equal(result.requests.length, 1);
+  }
+});
+
+
+test('interactive personal chat shows uncertainty without retrying it', async t => {
+  const result = await runChat(t, { success: false, intent: 'message_received', response: "I received this request, but I can't confirm whether it finished. Check the result before starting it again.", agent_id: 'agent-1' }, true);
+  assert.equal(result.code, 0, result.stderr);
+  assert.match(result.stdout, /can't confirm whether it finished/);
+  assert.equal(result.requests.length, 1);
+});