fix cursor vpn auth diagnostics

Add Cursor protected-network diagnostics and handle missing CA file configuration.

Author: ya-nsh

README.md

@@ -213,6 +213,7 @@ Use these commands to manage Cursor authentication and the local cache that Toke
 tokenleak cursor login --name work
 tokenleak cursor status
 tokenleak cursor accounts --json
+tokenleak cursor doctor
 tokenleak cursor switch work
 tokenleak cursor logout --name work
 tokenleak cursor logout --all --purge-cache
@@ -255,6 +256,28 @@ bun packages/cli/dist/cli.js --provider cursor --format json
 - If `cursor status` is valid but `--list-providers` still shows Cursor as unavailable, run `tokenleak --provider cursor` once to sync the cache, then rerun `--list-providers`.
 - Cursor session tokens are stored in plaintext at `~/.config/tokenleak/cursor-credentials.json` (or under `TOKENLEAK_CURSOR_DIR`) with local-only file permissions.
 
+#### Corporate VPN / protected network
+
+If `tokenleak cursor login` works off VPN but fails on a company protected VPN with a connection, proxy, or certificate error, run the token-free doctor first:
+
+```bash
+tokenleak cursor doctor
+```
+
+For managed proxy networks, pass a Cursor-specific proxy or use your standard shell proxy variables:
+
+```bash
+TOKENLEAK_CURSOR_PROXY=http://proxy.company:8080 tokenleak cursor doctor
+```
+
+For TLS inspection networks, export the company root CA as a PEM file and point Tokenleak at it:
+
+```bash
+TOKENLEAK_CURSOR_CA_FILE=/path/company-root-ca.pem tokenleak cursor doctor --with-token
+```
+
+Tokenleak also honors `HTTPS_PROXY`, `HTTP_PROXY`, `NO_PROXY`, and `TOKENLEAK_CURSOR_TIMEOUT_MS` for Cursor API requests. `tokenleak cursor doctor --insecure-skip-tls-verify` exists only to prove that TLS inspection is the failure mode; do not use it for normal login or sync.
+
 ### Date filtering
 
 By default, Tokenleak shows the last **90 days** of usage.

packages/cli/src/cursor.test.ts

@@ -9,6 +9,7 @@ import {
   loadCursorCredentialsStore,
   removeAllCursorAccounts,
   resetCursorProviderState,
+  runCursorCommand,
   saveCursorCredentials,
   setActiveCursorAccount,
   shouldSyncCursorForRun,
@@ -24,21 +25,47 @@ const SAMPLE_CSV = [
 ].join('\n');
 
 describe('cursor auth and sync helpers', () => {
-  const originalCursorDir = process.env['TOKENLEAK_CURSOR_DIR'];
   const originalFetch = globalThis.fetch;
+  const originalEnv = { ...process.env };
   let tempRoot = '';
 
   beforeEach(() => {
     tempRoot = mkdtempSync(join(tmpdir(), 'tokenleak-cursor-'));
     process.env['TOKENLEAK_CURSOR_DIR'] = tempRoot;
+    for (const key of [
+      'TOKENLEAK_CURSOR_PROXY',
+      'TOKENLEAK_CURSOR_CA_FILE',
+      'TOKENLEAK_CURSOR_TIMEOUT_MS',
+      'HTTPS_PROXY',
+      'https_proxy',
+      'HTTP_PROXY',
+      'http_proxy',
+      'NO_PROXY',
+      'no_proxy',
+    ]) {
+      delete process.env[key];
+    }
     globalThis.fetch = originalFetch;
   });
 
   afterEach(() => {
-    if (originalCursorDir === undefined) {
-      delete process.env['TOKENLEAK_CURSOR_DIR'];
-    } else {
-      process.env['TOKENLEAK_CURSOR_DIR'] = originalCursorDir;
+    for (const key of [
+      'TOKENLEAK_CURSOR_DIR',
+      'TOKENLEAK_CURSOR_PROXY',
+      'TOKENLEAK_CURSOR_CA_FILE',
+      'TOKENLEAK_CURSOR_TIMEOUT_MS',
+      'HTTPS_PROXY',
+      'https_proxy',
+      'HTTP_PROXY',
+      'http_proxy',
+      'NO_PROXY',
+      'no_proxy',
+    ]) {
+      if (originalEnv[key] === undefined) {
+        delete process.env[key];
+      } else {
+        process.env[key] = originalEnv[key];
+      }
     }
     globalThis.fetch = originalFetch;
     rmSync(tempRoot, { recursive: true, force: true });
@@ -168,4 +195,99 @@ describe('cursor auth and sync helpers', () => {
     expect(existsSync(join(getCursorCacheDir(), 'usage.csv'))).toBe(false);
     expect(listCursorAccounts()).toEqual([]);
   });
+
+  test('cursor help includes doctor diagnostics', async () => {
+    let output = '';
+    const originalWrite = process.stdout.write;
+    process.stdout.write = ((chunk: string | Uint8Array) => {
+      output += String(chunk);
+      return true;
+    }) as typeof process.stdout.write;
+
+    try {
+      await runCursorCommand(['--help']);
+    } finally {
+      process.stdout.write = originalWrite;
+    }
+
+    expect(output).toContain('tokenleak cursor doctor [--name <label>] [--with-token] [--insecure-skip-tls-verify]');
+  });
+
+  test('cursor doctor redacts proxy credentials and saved token details', async () => {
+    process.env['TOKENLEAK_CURSOR_PROXY'] = 'http://user:secret@proxy.company:8080';
+    saveCursorCredentials('user-work::super-secret-token', 'work');
+    globalThis.fetch = (async (url, init) => {
+      const cookie = String((init?.headers as Record<string, string> | undefined)?.['Cookie'] ?? '');
+      const hasToken = cookie.includes('super-secret-token');
+      if (String(url).includes('/api/usage-summary')) {
+        if (!hasToken) {
+          return new Response(JSON.stringify({ error: 'not_authenticated' }), { status: 401 });
+        }
+        return new Response(JSON.stringify({
+          billingCycleStart: '2026-03-01',
+          billingCycleEnd: '2026-03-31',
+          membershipType: 'pro',
+        }), { status: 200 });
+      }
+      if (!hasToken) {
+        return new Response('', { status: 307, headers: { location: 'https://api.workos.com' } });
+      }
+      return new Response(SAMPLE_CSV, { status: 200 });
+    }) as typeof fetch;
+
+    let output = '';
+    const originalWrite = process.stdout.write;
+    process.stdout.write = ((chunk: string | Uint8Array) => {
+      output += String(chunk);
+      return true;
+    }) as typeof process.stdout.write;
+
+    try {
+      await runCursorCommand(['doctor', '--name', 'work', '--with-token']);
+    } finally {
+      process.stdout.write = originalWrite;
+    }
+
+    expect(output).toContain('Cursor network doctor');
+    expect(output).toContain('Proxy: http://***:***@proxy.company:8080');
+    expect(output).toContain('Token check: enabled');
+    expect(output).not.toContain('super-secret-token');
+    expect(output).not.toContain('user:secret');
+    expect(output).not.toContain('Set-Cookie');
+  });
+
+  test('cursor login network errors point to doctor and Cursor network env vars', async () => {
+    globalThis.fetch = (async () => {
+      throw new Error('self signed certificate in certificate chain');
+    }) as typeof fetch;
+
+    await expect(validateCursorSession('token-123')).resolves.toMatchObject({
+      valid: false,
+      reason: 'network',
+      error: expect.stringContaining('TOKENLEAK_CURSOR_CA_FILE'),
+    });
+  });
+
+  test('cursor doctor reports a missing CA file without crashing', async () => {
+    const missingCaPath = join(tempRoot, 'missing-company-root-ca.pem');
+    process.env['TOKENLEAK_CURSOR_CA_FILE'] = missingCaPath;
+    let output = '';
+    const originalWrite = process.stdout.write;
+    process.stdout.write = ((chunk: string | Uint8Array) => {
+      output += String(chunk);
+      return true;
+    }) as typeof process.stdout.write;
+
+    try {
+      await runCursorCommand(['doctor']);
+    } finally {
+      process.stdout.write = originalWrite;
+    }
+
+    expect(output).toContain('Cursor network doctor');
+    expect(output).toContain('CA file:');
+    expect(output).toContain(missingCaPath);
+    expect(output).toContain('[fail] ca-file');
+    expect(output).toContain('TOKENLEAK_CURSOR_CA_FILE');
+  });
 });

packages/cli/src/cursor.ts

@@ -1,5 +1,6 @@
 import {
   CursorAuthError,
+  diagnoseCursorConnection,
   getActiveCursorCredentials,
   getCursorCacheDir,
   getCursorCredentialsFor,
@@ -19,6 +20,8 @@ import {
   type CursorAccountInfo,
   type CursorCredentials,
   type CursorCredentialsStore,
+  type CursorDiagnosticCheck,
+  type CursorDiagnosticResult,
   type SyncCursorResult,
   type ValidateCursorSessionResult,
 } from '@tokenleak/registry';
@@ -43,11 +46,14 @@ export {
   shouldSyncCursorForRun,
   syncCursorCache,
   validateCursorSession,
+  diagnoseCursorConnection,
 };
 export type {
   CursorAccountInfo,
   CursorCredentials,
   CursorCredentialsStore,
+  CursorDiagnosticCheck,
+  CursorDiagnosticResult,
   SyncCursorResult,
   ValidateCursorSessionResult,
 };
@@ -118,6 +124,7 @@ export function buildCursorHelpText(): string {
     'Usage:',
     '  tokenleak cursor login [--name <label>]',
     '  tokenleak cursor status [--name <label>]',
+    '  tokenleak cursor doctor [--name <label>] [--with-token] [--insecure-skip-tls-verify]',
     '  tokenleak cursor accounts [--json]',
     '  tokenleak cursor switch <name-or-id>',
     '  tokenleak cursor logout [--name <label> | --all] [--purge-cache]',
@@ -126,12 +133,40 @@ export function buildCursorHelpText(): string {
     'Notes:',
     '  Session tokens come from https://www.cursor.com/settings',
     '  Session tokens are stored in plaintext with local-only file permissions.',
+    '  For protected VPN/proxy networks, run: tokenleak cursor doctor',
     `  Credentials: ${getCursorCredentialsPath()}`,
     `  Cache: ${getCursorCacheDir()}`,
     '',
   ].join('\n');
 }
 
+function formatDiagnosticCheck(check: CursorDiagnosticCheck): string {
+  const prefix = check.ok ? '[ok]' : '[fail]';
+  const status = check.status === undefined ? '' : ` HTTP ${check.status}`;
+  const kind = check.kind ? ` ${check.kind}` : '';
+  const hint = check.hint ? `\n       Hint: ${check.hint}` : '';
+  return `  ${prefix} ${check.name}${status}${kind}: ${check.message}${hint}`;
+}
+
+function printCursorDoctorResult(result: CursorDiagnosticResult, tokenEnabled: boolean): void {
+  process.stdout.write('Cursor network doctor\n');
+  process.stdout.write(`Timeout: ${result.network.timeoutMs}ms\n`);
+  process.stdout.write(`Proxy: ${result.network.proxy ?? 'not configured'}\n`);
+  if (result.network.proxySource) {
+    process.stdout.write(`Proxy source: ${result.network.proxySource}\n`);
+  }
+  if (result.network.noProxyMatched) {
+    process.stdout.write('Proxy bypass: matched NO_PROXY/no_proxy\n');
+  }
+  process.stdout.write(`CA file: ${result.network.caFile ?? 'not configured'}\n`);
+  process.stdout.write(`TLS verification: ${result.network.tlsVerification}\n`);
+  process.stdout.write(`Token check: ${tokenEnabled ? 'enabled' : 'disabled'}\n`);
+  process.stdout.write('Checks:\n');
+  for (const check of result.checks) {
+    process.stdout.write(`${formatDiagnosticCheck(check)}\n`);
+  }
+}
+
 function printCursorAccounts(json: boolean): void {
   const accounts = listCursorAccounts();
   if (json) {
@@ -193,6 +228,27 @@ async function runCursorStatus(name?: string): Promise<void> {
   }
 }
 
+async function runCursorDoctor(options: {
+  name?: string;
+  withToken: boolean;
+  insecureSkipTlsVerify: boolean;
+}): Promise<void> {
+  let credentials: CursorCredentials | null = null;
+  if (options.withToken) {
+    credentials = options.name ? getCursorCredentialsFor(options.name) : getActiveCursorCredentials();
+    if (!credentials) {
+      throw new TokenleakError(options.name ? `Account not found: ${options.name}` : 'No saved Cursor accounts');
+    }
+  }
+
+  const result = await diagnoseCursorConnection({
+    credentials,
+    includeToken: options.withToken,
+    insecureSkipTlsVerify: options.insecureSkipTlsVerify,
+  });
+  printCursorDoctorResult(result, options.withToken);
+}
+
 function runCursorLogout(name: string | undefined, all: boolean, purgeCache: boolean): void {
   if (all) {
     removeAllCursorAccounts(purgeCache);
@@ -278,6 +334,37 @@ export async function runCursorCommand(argv: string[]): Promise<void> {
     return;
   }
 
+  if (command === 'doctor') {
+    let name: string | undefined;
+    let withToken = false;
+    let insecureSkipTlsVerify = false;
+    for (let index = 1; index < argv.length; ) {
+      const arg = argv[index]!;
+      if (arg === '--name') {
+        [name, index] = parseNameFlag(argv, index);
+        continue;
+      }
+      if (arg === '--with-token') {
+        withToken = true;
+        index += 1;
+        continue;
+      }
+      if (arg === '--insecure-skip-tls-verify') {
+        insecureSkipTlsVerify = true;
+        index += 1;
+        continue;
+      }
+      throw new TokenleakError(`Unknown cursor doctor flag "${arg}"`);
+    }
+
+    try {
+      await runCursorDoctor({ name, withToken, insecureSkipTlsVerify });
+    } catch (error: unknown) {
+      wrapCursorError(error);
+    }
+    return;
+  }
+
   if (command === 'accounts') {
     if (argv.length > 2 || (argv[1] && argv[1] !== '--json')) {
       throw new TokenleakError(`Unknown cursor flag "${argv[1]}"`);