diff --git a/CLAUDE.md b/CLAUDE.md
index 0651b85..1bf1b3a 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -12,7 +12,7 @@ WorkOS CLI for installing AuthKit integrations and managing WorkOS resources (or
 ## Non-TTY Behavior
 
 - **Output**: Auto-switches to JSON when piped or `--json` flag. `WORKOS_FORCE_TTY=1` overrides.
-- **Auth**: Exits code 4 instead of opening browser. Requires prior `workos login` or `WORKOS_API_KEY` env var.
+- **Auth**: Exits code 4 instead of opening browser. Requires prior `workos auth login` or `WORKOS_API_KEY` env var.
 - **Errors**: Structured JSON to stderr: `{ "error": { "code": "...", "message": "..." } }`
 - **Exit codes**: 0=success, 1=error, 2=cancelled, 4=auth required (follows `gh` CLI convention)
 - **Headless flags**: `--no-branch`, `--no-commit`, `--create-pr`, `--no-git-check`
diff --git a/DEVELOPMENT.md b/DEVELOPMENT.md
index f4eadac..2eb83bd 100644
--- a/DEVELOPMENT.md
+++ b/DEVELOPMENT.md
@@ -26,8 +26,9 @@ src/
 │   ├── user.ts               # workos user (get/list/update/delete)
 │   ├── install.ts            # workos install
 │   ├── install-skill.ts      # workos install-skill
-│   ├── login.ts              # workos login
-│   └── logout.ts             # workos logout
+│   ├── auth-status.ts        # workos auth status
+│   ├── login.ts              # workos auth login
+│   └── logout.ts             # workos auth logout
 ├── dashboard/                # Ink/React TUI components
 ├── nextjs/                   # Next.js installer agent
 ├── react/                    # React SPA installer agent
diff --git a/README.md b/README.md
index 7a4571c..d1b6e1f 100644
--- a/README.md
+++ b/README.md
@@ -470,10 +470,13 @@ The CLI uses WorkOS Connect OAuth device flow for authentication:
 
 ```bash
 # Login (opens browser for authentication)
-workos login
+workos auth login
+
+# Check current auth status
+workos auth status
 
 # Logout (clears stored credentials)
-workos logout
+workos auth logout
 ```
 
 OAuth credentials are stored in the system keychain (with `~/.workos/credentials.json` fallback). Access tokens are not persisted long-term for security - users re-authenticate when tokens expire.
diff --git a/skills/workos-management/SKILL.md b/skills/workos-management/SKILL.md
index 62bb81d..4d9a605 100644
--- a/skills/workos-management/SKILL.md
+++ b/skills/workos-management/SKILL.md
@@ -5,7 +5,7 @@ description: Manage WorkOS resources (orgs, users, roles, SSO, directories, webh
 
 # WorkOS Management Commands
 
-Use these commands to manage WorkOS resources directly from the terminal. The CLI must be authenticated via `workos login` or `WORKOS_API_KEY` env var.
+Use these commands to manage WorkOS resources directly from the terminal. The CLI must be authenticated via `workos auth login` or `WORKOS_API_KEY` env var.
 
 All commands support `--json` for structured output. Use `--json` when you need to parse output (e.g., extract an ID).
 
diff --git a/src/bin.ts b/src/bin.ts
index 87c1b24..5891d0f 100644
--- a/src/bin.ts
+++ b/src/bin.ts
@@ -28,7 +28,7 @@ if (!satisfies(process.version, NODE_VERSION_RANGE)) {
 }
 
 import { isNonInteractiveEnvironment } from './utils/environment.js';
-import { resolveOutputMode, setOutputMode, outputJson, exitWithError } from './utils/output.js';
+import { resolveOutputMode, setOutputMode, isJsonMode, outputJson, exitWithError } from './utils/output.js';
 import clack from './utils/clack.js';
 import { registerSubcommand } from './utils/register-subcommand.js';
 
@@ -177,8 +177,8 @@ const installerOptions = {
   },
 };
 
-// Check for updates (blocks up to 500ms)
-await checkForUpdates();
+// Check for updates (blocks up to 500ms, skip in JSON mode to keep stdout clean)
+if (!isJsonMode()) await checkForUpdates();
 
 yargs(rawArgs)
   .env('WORKOS_INSTALLER')
@@ -188,16 +188,43 @@ yargs(rawArgs)
     describe: 'Output results as JSON (auto-enabled in non-TTY)',
     global: true,
   })
-  .command('login', 'Authenticate with WorkOS via browser-based OAuth', insecureStorageOption, async (argv) => {
-    await applyInsecureStorage(argv.insecureStorage);
-    const { runLogin } = await import('./commands/login.js');
-    await runLogin();
-    process.exit(0);
-  })
-  .command('logout', 'Remove stored WorkOS credentials and tokens', insecureStorageOption, async (argv) => {
-    await applyInsecureStorage(argv.insecureStorage);
-    const { runLogout } = await import('./commands/logout.js');
-    await runLogout();
+  .command('auth', 'Manage authentication (login, logout, status)', (yargs) => {
+    yargs.options(insecureStorageOption);
+    registerSubcommand(
+      yargs,
+      'login',
+      'Authenticate with WorkOS via browser-based OAuth',
+      (y) => y,
+      async (argv) => {
+        await applyInsecureStorage(argv.insecureStorage);
+        const { runLogin } = await import('./commands/login.js');
+        await runLogin();
+        process.exit(0);
+      },
+    );
+    registerSubcommand(
+      yargs,
+      'logout',
+      'Remove stored WorkOS credentials and tokens',
+      (y) => y,
+      async (argv) => {
+        await applyInsecureStorage(argv.insecureStorage);
+        const { runLogout } = await import('./commands/logout.js');
+        await runLogout();
+      },
+    );
+    registerSubcommand(
+      yargs,
+      'status',
+      'Show current authentication status',
+      (y) => y,
+      async (argv) => {
+        await applyInsecureStorage(argv.insecureStorage);
+        const { runAuthStatus } = await import('./commands/auth-status.js');
+        await runAuthStatus();
+      },
+    );
+    return yargs.demandCommand(1, 'Please specify an auth subcommand').strict();
   })
   .command(
     'install-skill',
diff --git a/src/commands/auth-status.ts b/src/commands/auth-status.ts
new file mode 100644
index 0000000..c59e03b
--- /dev/null
+++ b/src/commands/auth-status.ts
@@ -0,0 +1,60 @@
+import chalk from 'chalk';
+import { getCredentials, isTokenExpired } from '../lib/credentials.js';
+import { getActiveEnvironment } from '../lib/config-store.js';
+import { isJsonMode, outputJson } from '../utils/output.js';
+
+function formatTimeRemaining(ms: number): string {
+  if (ms <= 0) return 'expired';
+  const seconds = Math.floor(ms / 1000);
+  const minutes = Math.floor(seconds / 60);
+  const hours = Math.floor(minutes / 60);
+  if (hours > 0) return `${hours}h ${minutes % 60}m`;
+  if (minutes > 0) return `${minutes}m ${seconds % 60}s`;
+  return `${seconds}s`;
+}
+
+export async function runAuthStatus(): Promise<void> {
+  const creds = getCredentials();
+  const activeEnv = getActiveEnvironment();
+
+  if (!creds) {
+    if (isJsonMode()) {
+      outputJson({ authenticated: false });
+      return;
+    }
+    console.log(chalk.yellow('Not logged in'));
+    console.log(chalk.dim('Run `workos auth login` to authenticate'));
+    return;
+  }
+
+  const expired = isTokenExpired(creds);
+  const timeRemaining = creds.expiresAt - Date.now();
+
+  if (isJsonMode()) {
+    outputJson({
+      authenticated: true,
+      email: creds.email ?? null,
+      userId: creds.userId,
+      tokenExpired: expired,
+      tokenExpiresAt: new Date(creds.expiresAt).toISOString(),
+      tokenExpiresIn: expired ? null : formatTimeRemaining(timeRemaining),
+      hasRefreshToken: !!creds.refreshToken,
+      activeEnvironment: activeEnv ? { name: activeEnv.name, type: activeEnv.type } : null,
+    });
+    return;
+  }
+
+  console.log(chalk.green(`Logged in as ${creds.email ?? creds.userId}`));
+
+  if (expired) {
+    console.log(chalk.yellow(`Token expired ${formatTimeRemaining(-timeRemaining)} ago`));
+  } else {
+    console.log(chalk.dim(`Token expires in ${formatTimeRemaining(timeRemaining)}`));
+  }
+
+  console.log(chalk.dim(`Refresh token: ${creds.refreshToken ? 'present' : 'absent'}`));
+
+  if (activeEnv) {
+    console.log(chalk.dim(`Environment: ${activeEnv.name} (${activeEnv.type})`));
+  }
+}
diff --git a/src/commands/login.ts b/src/commands/login.ts
index 5b73276..6c612b0 100644
--- a/src/commands/login.ts
+++ b/src/commands/login.ts
@@ -1,4 +1,5 @@
 import open from 'opn';
+import chalk from 'chalk';
 import clack from '../utils/clack.js';
 import { saveCredentials, getCredentials, getAccessToken, isTokenExpired, updateTokens } from '../lib/credentials.js';
 import { getCliAuthClientId, getAuthkitDomain } from '../lib/settings.js';
@@ -76,8 +77,8 @@ export async function runLogin(): Promise<void> {
   // Check if already logged in with valid token
   if (getAccessToken()) {
     const creds = getCredentials();
-    clack.log.info(`Already logged in as ${creds?.email ?? 'unknown'}`);
-    clack.log.info('Run `workos logout` to log out');
+    console.log(chalk.green(`Already logged in as ${creds?.email ?? 'unknown'}`));
+    console.log(chalk.dim('Run `workos auth logout` to log out'));
     return;
   }
 
@@ -90,8 +91,8 @@ export async function runLogin(): Promise<void> {
       if (result.accessToken && result.expiresAt) {
         updateTokens(result.accessToken, result.expiresAt, result.refreshToken);
         logInfo('[login] Session refreshed via refresh token');
-        clack.log.info(`Already logged in as ${existingCreds.email ?? 'unknown'}`);
-        clack.log.info('Run `workos logout` to log out');
+        console.log(chalk.green(`Already logged in as ${existingCreds.email ?? 'unknown'}`));
+        console.log(chalk.dim('Run `workos auth logout` to log out'));
         return;
       }
     } catch {
diff --git a/src/doctor/checks/ai-analysis.ts b/src/doctor/checks/ai-analysis.ts
index 43f09bf..0b25b39 100644
--- a/src/doctor/checks/ai-analysis.ts
+++ b/src/doctor/checks/ai-analysis.ts
@@ -61,10 +61,10 @@ async function callModel(prompt: string, model: string): Promise<string> {
   if (!creds) throw new Error('Not authenticated');
 
   if (isTokenExpired(creds)) {
-    if (!creds.refreshToken) throw new Error('Session expired — run `workos login` to re-authenticate');
+    if (!creds.refreshToken) throw new Error('Session expired — run `workos auth login` to re-authenticate');
     const result = await refreshAccessToken(getAuthkitDomain(), getCliAuthClientId());
     if (!result.success || !result.accessToken || !result.expiresAt) {
-      throw new Error('Session expired — run `workos login` to re-authenticate');
+      throw new Error('Session expired — run `workos auth login` to re-authenticate');
     }
     updateTokens(result.accessToken, result.expiresAt, result.refreshToken);
     creds = getCredentials()!;
@@ -111,7 +111,7 @@ export async function checkAiAnalysis(context: AnalysisContext, options: { skipA
       process.stderr.write(`    ${line}\n`);
     }
     process.stderr.write('\n');
-    return skippedResult('Not authenticated — run `workos login` for AI-powered analysis');
+    return skippedResult('Not authenticated — run `workos auth login` for AI-powered analysis');
   }
 
   const startTime = Date.now();
diff --git a/src/lib/adapters/cli-adapter.ts b/src/lib/adapters/cli-adapter.ts
index 085c346..9bed10f 100644
--- a/src/lib/adapters/cli-adapter.ts
+++ b/src/lib/adapters/cli-adapter.ts
@@ -406,7 +406,7 @@ export class CLIAdapter implements InstallerAdapter {
 
     // Add actionable hints for common errors
     if (message.includes('authentication') || message.includes('auth')) {
-      clack.log.info('Try running: workos logout && workos install');
+      clack.log.info('Try running: workos auth logout && workos install');
     }
     if (message.includes('ENOENT') || message.includes('not found')) {
       clack.log.info('Ensure you are in a project directory');
diff --git a/src/lib/agent-interface.ts b/src/lib/agent-interface.ts
index 33a73bf..557438c 100644
--- a/src/lib/agent-interface.ts
+++ b/src/lib/agent-interface.ts
@@ -3,7 +3,6 @@
  * Uses Claude Agent SDK directly with WorkOS MCP server
  */
 
-import path from 'path';
 import { getPackageRoot } from '../utils/paths.js';
 import { debug, logInfo, logWarn, logError, initLogFile, getLogFilePath } from '../utils/debug.js';
 import type { InstallerOptions } from '../utils/types.js';
@@ -361,12 +360,12 @@ export async function initializeAgent(config: AgentConfig, options: InstallerOpt
       // Check/refresh authentication for production (unless skipping auth)
       if (!options.skipAuth && !options.local) {
         if (!hasCredentials()) {
-          throw new Error('Not authenticated. Run `workos login` to authenticate.');
+          throw new Error('Not authenticated. Run `workos auth login` to authenticate.');
         }
 
         const creds = getCredentials();
         if (!creds) {
-          throw new Error('Not authenticated. Run `workos login` to authenticate.');
+          throw new Error('Not authenticated. Run `workos auth login` to authenticate.');
         }
 
         // Check if we have refresh token capability and proxy is not disabled
@@ -387,7 +386,7 @@ export async function initializeAgent(config: AgentConfig, options: InstallerOpt
               onRefreshExpired: () => {
                 logError('[agent-interface] Session expired, refresh token invalid');
                 options.emitter?.emit('error', {
-                  message: 'Session expired. Run `workos login` to re-authenticate.',
+                  message: 'Session expired. Run `workos auth login` to re-authenticate.',
                 });
               },
             },
@@ -404,9 +403,9 @@ export async function initializeAgent(config: AgentConfig, options: InstallerOpt
           // No refresh token OR proxy disabled - fall back to old behavior (5 min limit)
           if (!creds.refreshToken) {
             logWarn('[agent-interface] No refresh token available, session limited to 5 minutes');
-            logWarn('[agent-interface] Run `workos login` to enable extended sessions');
+            logWarn('[agent-interface] Run `workos auth login` to enable extended sessions');
             options.emitter?.emit('status', {
-              message: 'Note: Run `workos login` to enable extended sessions',
+              message: 'Note: Run `workos auth login` to enable extended sessions',
             });
           } else {
             logWarn('[agent-interface] Proxy disabled via INSTALLER_DISABLE_PROXY');
diff --git a/src/lib/credential-proxy.ts b/src/lib/credential-proxy.ts
index 63638bf..7b7b895 100644
--- a/src/lib/credential-proxy.ts
+++ b/src/lib/credential-proxy.ts
@@ -251,7 +251,7 @@ async function handleRequest(
     res.end(
       JSON.stringify({
         error: 'credentials_unavailable',
-        message: 'Not authenticated. Run `workos login` first.',
+        message: 'Not authenticated. Run `workos auth login` first.',
       }),
     );
     return;
diff --git a/src/lib/ensure-auth.ts b/src/lib/ensure-auth.ts
index 8e0be91..ba47ba8 100644
--- a/src/lib/ensure-auth.ts
+++ b/src/lib/ensure-auth.ts
@@ -77,7 +77,9 @@ export async function ensureAuthenticated(): Promise<EnsureAuthResult> {
       if (refreshResult.errorType === 'invalid_grant') {
         clearCredentials();
         if (isNonInteractiveEnvironment()) {
-          exitWithAuthRequired('Session expired. Run `workos login` in an interactive terminal to re-authenticate.');
+          exitWithAuthRequired(
+            'Session expired. Run `workos auth login` in an interactive terminal to re-authenticate.',
+          );
         }
         logInfo('[ensure-auth] Refresh token expired, triggering login');
         await runLogin();
@@ -89,7 +91,7 @@ export async function ensureAuthenticated(): Promise<EnsureAuthResult> {
       // Network or server error - keep credentials intact for retry
       if (isNonInteractiveEnvironment()) {
         exitWithAuthRequired(
-          `Authentication refresh failed (${refreshResult.errorType}). Run \`workos login\` in an interactive terminal.`,
+          `Authentication refresh failed (${refreshResult.errorType}). Run \`workos auth login\` in an interactive terminal.`,
         );
       }
       logInfo(`[ensure-auth] Refresh failed (${refreshResult.errorType}), triggering login`);
@@ -103,7 +105,7 @@ export async function ensureAuthenticated(): Promise<EnsureAuthResult> {
   // Case 4: No refresh token available — clear stale creds, must login
   clearCredentials();
   if (isNonInteractiveEnvironment()) {
-    exitWithAuthRequired('Session expired. Run `workos login` in an interactive terminal to re-authenticate.');
+    exitWithAuthRequired('Session expired. Run `workos auth login` in an interactive terminal to re-authenticate.');
   }
   logInfo('[ensure-auth] No refresh token, triggering login');
   await runLogin();
diff --git a/src/lib/run-with-core.ts b/src/lib/run-with-core.ts
index 57bcbc8..b7f47c1 100644
--- a/src/lib/run-with-core.ts
+++ b/src/lib/run-with-core.ts
@@ -223,7 +223,7 @@ export async function runWithCore(options: InstallerOptions): Promise<void> {
         if (!token) {
           // This should rarely happen since bin.ts handles auth first
           // But keep as safety net for programmatic usage
-          throw new Error('Not authenticated. Run `workos login` first.');
+          throw new Error('Not authenticated. Run `workos auth login` first.');
         }
 
         // Set telemetry from existing credentials
diff --git a/src/lib/token-refresh-client.ts b/src/lib/token-refresh-client.ts
index ad7fb1c..7952a07 100644
--- a/src/lib/token-refresh-client.ts
+++ b/src/lib/token-refresh-client.ts
@@ -73,7 +73,7 @@ export async function refreshAccessToken(authkitDomain: string, clientId: string
       if (errorData.error === 'invalid_grant') {
         return {
           success: false,
-          error: 'Session expired. Run `workos login` to re-authenticate.',
+          error: 'Session expired. Run `workos auth login` to re-authenticate.',
           errorType: 'invalid_grant',
         };
       }
diff --git a/src/lib/token-refresh.spec.ts b/src/lib/token-refresh.spec.ts
index 2b88884..4f04e42 100644
--- a/src/lib/token-refresh.spec.ts
+++ b/src/lib/token-refresh.spec.ts
@@ -92,7 +92,7 @@ describe('token-refresh', () => {
 
       expect(result.success).toBe(false);
       expect(result.error).toContain('Session expired');
-      expect(result.error).toContain('workos login');
+      expect(result.error).toContain('workos auth login');
     });
 
     it('preserves credentials on valid token', async () => {
diff --git a/src/lib/token-refresh.ts b/src/lib/token-refresh.ts
index 709ece1..8430607 100644
--- a/src/lib/token-refresh.ts
+++ b/src/lib/token-refresh.ts
@@ -27,7 +27,7 @@ export async function ensureValidToken(): Promise<TokenValidationResult> {
     logInfo('[ensureValidToken] Token expired, re-authentication required');
     return {
       success: false,
-      error: 'Session expired. Run `workos login` to re-authenticate.',
+      error: 'Session expired. Run `workos auth login` to re-authenticate.',
     };
   }
 
diff --git a/src/lib/version-check.ts b/src/lib/version-check.ts
index 357f0d6..4fc9c4e 100644
--- a/src/lib/version-check.ts
+++ b/src/lib/version-check.ts
@@ -37,7 +37,8 @@ export async function checkForUpdates(): Promise<void> {
     if (lt(currentVersion, latestVersion)) {
       hasWarned = true;
       yellow(`Update available: ${currentVersion} → ${latestVersion}`);
-      dim(`Run: npx workos@latest`);
+      dim('Run: npx workos@latest');
+      console.log();
     }
   } catch {
     // Silently ignore all errors (timeout, network, parse, etc.)
diff --git a/src/utils/exit-codes.ts b/src/utils/exit-codes.ts
index 3cfc111..ab77f8f 100644
--- a/src/utils/exit-codes.ts
+++ b/src/utils/exit-codes.ts
@@ -30,6 +30,6 @@ export function exitWithCode(code: ExitCodeValue, error?: { code: string; messag
 export function exitWithAuthRequired(message?: string): never {
   exitWithCode(ExitCode.AUTH_REQUIRED, {
     code: 'auth_required',
-    message: message ?? 'Not authenticated. Run `workos login` in an interactive terminal, or set WORKOS_API_KEY.',
+    message: message ?? 'Not authenticated. Run `workos auth login` in an interactive terminal, or set WORKOS_API_KEY.',
   });
 }
diff --git a/src/utils/help-json.spec.ts b/src/utils/help-json.spec.ts
index 08a9bf2..4744301 100644
--- a/src/utils/help-json.spec.ts
+++ b/src/utils/help-json.spec.ts
@@ -29,8 +29,9 @@ describe('help-json', () => {
       const names = (tree as { commands: { name: string }[] }).commands.map((c) => c.name);
       expect(names).toEqual(
         expect.arrayContaining([
-          'login',
-          'logout',
+          'auth login',
+          'auth logout',
+          'auth status',
           'install-skill',
           'doctor',
           'env',
diff --git a/src/utils/help-json.ts b/src/utils/help-json.ts
index 6d46bc4..f8a44cb 100644
--- a/src/utils/help-json.ts
+++ b/src/utils/help-json.ts
@@ -96,15 +96,20 @@ const paginationOpts: OptionSchema[] = [
 
 const commands: CommandSchema[] = [
   {
-    name: 'login',
+    name: 'auth login',
     description: 'Authenticate with WorkOS via browser-based OAuth',
     options: [insecureStorageOpt],
   },
   {
-    name: 'logout',
+    name: 'auth logout',
     description: 'Remove stored WorkOS credentials and tokens',
     options: [insecureStorageOpt],
   },
+  {
+    name: 'auth status',
+    description: 'Show current authentication status',
+    options: [insecureStorageOpt],
+  },
   {
     name: 'install-skill',
     description: 'Install bundled AuthKit skills to coding agents (Claude Code, Codex, Cursor, Goose)',