From f41c1620091185a65239e2169c1d402a731a916d Mon Sep 17 00:00:00 2001
From: Pankaj Garg <pankajn17@gmail.com>
Date: Fri, 24 Apr 2026 08:42:10 +0200
Subject: [PATCH] detect setup auth ping failures

---
 setup/lib/agent-ping.test.ts | 30 ++++++++++++++++++++++++++++++
 setup/lib/agent-ping.ts      | 24 ++++++++++++++++++++----
 setup/verify.ts              |  2 +-
 3 files changed, 51 insertions(+), 5 deletions(-)
 create mode 100644 setup/lib/agent-ping.test.ts

diff --git a/setup/lib/agent-ping.test.ts b/setup/lib/agent-ping.test.ts
new file mode 100644
index 000000000..5f2be2cd9
--- /dev/null
+++ b/setup/lib/agent-ping.test.ts
@@ -0,0 +1,30 @@
+import { describe, expect, it } from 'vitest';
+
+import { classifyPingResult } from './agent-ping.js';
+
+describe('classifyPingResult', () => {
+  it('treats a normal text reply as ok', () => {
+    expect(classifyPingResult(0, 'pong\n')).toBe('ok');
+  });
+
+  it('detects Anthropic auth errors printed as a chat reply', () => {
+    expect(
+      classifyPingResult(
+        0,
+        'Failed to authenticate. API Error: 401 {"type":"error","error":{"type":"authentication_error","message":"Invalid bearer token"}}',
+      ),
+    ).toBe('auth_error');
+  });
+
+  it('detects auth errors on stderr too', () => {
+    expect(classifyPingResult(1, '', 'Authentication error')).toBe('auth_error');
+  });
+
+  it('preserves socket errors', () => {
+    expect(classifyPingResult(2, '')).toBe('socket_error');
+  });
+
+  it('treats empty output as no reply', () => {
+    expect(classifyPingResult(0, '')).toBe('no_reply');
+  });
+});
diff --git a/setup/lib/agent-ping.ts b/setup/lib/agent-ping.ts
index 8c5127f00..49c5fe294 100644
--- a/setup/lib/agent-ping.ts
+++ b/setup/lib/agent-ping.ts
@@ -13,7 +13,21 @@
  */
 import { spawn } from 'child_process';
 
-export type PingResult = 'ok' | 'no_reply' | 'socket_error';
+export type PingResult = 'ok' | 'no_reply' | 'socket_error' | 'auth_error';
+
+export function classifyPingResult(exitCode: number | null, stdout: string, stderr = ''): PingResult {
+  const output = `${stdout}\n${stderr}`;
+  if (
+    /Invalid bearer token/i.test(output) ||
+    /authentication[_ ]error/i.test(output) ||
+    /Failed to authenticate/i.test(output)
+  ) {
+    return 'auth_error';
+  }
+  if (exitCode === 2) return 'socket_error';
+  if (exitCode === 0 && stdout.trim().length > 0) return 'ok';
+  return 'no_reply';
+}
 
 export function pingCliAgent(timeoutMs = 30_000): Promise<PingResult> {
   return new Promise((resolve) => {
@@ -21,6 +35,7 @@ export function pingCliAgent(timeoutMs = 30_000): Promise<PingResult> {
       stdio: ['ignore', 'pipe', 'pipe'],
     });
     let stdout = '';
+    let stderr = '';
     let settled = false;
     const timer = setTimeout(() => {
       if (settled) return;
@@ -32,13 +47,14 @@ export function pingCliAgent(timeoutMs = 30_000): Promise<PingResult> {
     child.stdout.on('data', (chunk: Buffer) => {
       stdout += chunk.toString('utf-8');
     });
+    child.stderr.on('data', (chunk: Buffer) => {
+      stderr += chunk.toString('utf-8');
+    });
     child.on('close', (code) => {
       if (settled) return;
       settled = true;
       clearTimeout(timer);
-      if (code === 2) resolve('socket_error');
-      else if (code === 0 && stdout.trim().length > 0) resolve('ok');
-      else resolve('no_reply');
+      resolve(classifyPingResult(code, stdout, stderr));
     });
     child.on('error', () => {
       if (settled) return;
diff --git a/setup/verify.ts b/setup/verify.ts
index 281b243ce..873af66ff 100644
--- a/setup/verify.ts
+++ b/setup/verify.ts
@@ -220,7 +220,7 @@ export async function run(_args: string[]): Promise<void> {
 
   // 7. End-to-end: ping the CLI agent and confirm it replies. Only run if
   // everything upstream looks healthy, since a broken socket would just hang.
-  let agentPing: 'ok' | 'no_reply' | 'socket_error' | 'skipped' = 'skipped';
+  let agentPing: 'ok' | 'no_reply' | 'socket_error' | 'auth_error' | 'skipped' = 'skipped';
   if (service === 'running' && registeredGroups > 0) {
     log.info('Pinging CLI agent');
     agentPing = await pingCliAgent();