deplyze-code 0.1.0

package/src/utils/auth.ts

@@ -0,0 +1,2004 @@
+import chalk from 'chalk'
+import { exec } from 'child_process'
+import { execa } from 'execa'
+import { mkdir, stat } from 'fs/promises'
+import memoize from 'lodash-es/memoize.js'
+import { join } from 'path'
+import { CLAUDE_AI_PROFILE_SCOPE } from 'src/constants/oauth.js'
+import {
+  type AnalyticsMetadata_I_VERIFIED_THIS_IS_NOT_CODE_OR_FILEPATHS,
+  logEvent,
+} from 'src/services/analytics/index.js'
+import { getModelStrings } from 'src/utils/model/modelStrings.js'
+import { getAPIProvider } from 'src/utils/model/providers.js'
+import {
+  getIsNonInteractiveSession,
+  preferThirdPartyAuthentication,
+} from '../bootstrap/state.js'
+import {
+  getMockSubscriptionType,
+  shouldUseMockSubscription,
+} from '../services/mockRateLimits.js'
+import {
+  isOAuthTokenExpired,
+  refreshOAuthToken,
+  shouldUseClaudeAIAuth,
+} from '../services/oauth/client.js'
+import { getOauthProfileFromOauthToken } from '../services/oauth/getOauthProfile.js'
+import type { OAuthTokens, SubscriptionType } from '../services/oauth/types.js'
+import {
+  getApiKeyFromFileDescriptor,
+  getOAuthTokenFromFileDescriptor,
+} from './authFileDescriptor.js'
+import {
+  maybeRemoveApiKeyFromMacOSKeychainThrows,
+  normalizeApiKeyForConfig,
+} from './authPortable.js'
+import {
+  checkStsCallerIdentity,
+  clearAwsIniCache,
+  isValidAwsStsOutput,
+} from './aws.js'
+import { AwsAuthStatusManager } from './awsAuthStatusManager.js'
+import { clearBetasCaches } from './betas.js'
+import {
+  type AccountInfo,
+  checkHasTrustDialogAccepted,
+  getGlobalConfig,
+  saveGlobalConfig,
+} from './config.js'
+import { logAntError, logForDebugging } from './debug.js'
+import {
+  getClaudeConfigHomeDir,
+  isBareMode,
+  isEnvTruthy,
+  isRunningOnHomespace,
+} from './envUtils.js'
+import { errorMessage } from './errors.js'
+import { execSyncWithDefaults_DEPRECATED } from './execFileNoThrow.js'
+import * as lockfile from './lockfile.js'
+import { logError } from './log.js'
+import { memoizeWithTTLAsync } from './memoize.js'
+import { getSecureStorage } from './secureStorage/index.js'
+import {
+  clearLegacyApiKeyPrefetch,
+  getLegacyApiKeyPrefetchResult,
+} from './secureStorage/keychainPrefetch.js'
+import {
+  clearKeychainCache,
+  getMacOsKeychainStorageServiceName,
+  getUsername,
+} from './secureStorage/macOsKeychainHelpers.js'
+import {
+  getSettings_DEPRECATED,
+  getSettingsForSource,
+} from './settings/settings.js'
+import { sleep } from './sleep.js'
+import { jsonParse } from './slowOperations.js'
+import { clearToolSchemaCache } from './toolSchemaCache.js'
+
+/** Default TTL for API key helper cache in milliseconds (5 minutes) */
+const DEFAULT_API_KEY_HELPER_TTL = 5 * 60 * 1000
+
+/**
+ * CCR and Claude Desktop spawn the CLI with OAuth and should never fall back
+ * to the user's ~/.claude/settings.json API-key config (apiKeyHelper,
+ * env.ANTHROPIC_API_KEY, env.ANTHROPIC_AUTH_TOKEN). Those settings exist for
+ * the user's terminal CLI, not managed sessions. Without this guard, a user
+ * who runs `claude` in their terminal with an API key sees every CCD session
+ * also use that key — and fail if it's stale/wrong-org.
+ */
+function isManagedOAuthContext(): boolean {
+  return (
+    isEnvTruthy(process.env.CLAUDE_CODE_REMOTE) ||
+    process.env.CLAUDE_CODE_ENTRYPOINT === 'claude-desktop'
+  )
+}
+
+/** Whether we are supporting direct 1P auth. */
+// this code is closely related to getAuthTokenSource
+export function isAnthropicAuthEnabled(): boolean {
+  // --bare: API-key-only, never OAuth.
+  if (isBareMode()) return false
+
+  // `claude ssh` remote: ANTHROPIC_UNIX_SOCKET tunnels API calls through a
+  // local auth-injecting proxy. The launcher sets CLAUDE_CODE_OAUTH_TOKEN as a
+  // placeholder iff the local side is a subscriber (so the remote includes the
+  // oauth-2025 beta header to match what the proxy will inject). The remote's
+  // ~/.claude settings (apiKeyHelper, settings.env.ANTHROPIC_API_KEY) MUST NOT
+  // flip this — they'd cause a header mismatch with the proxy and a bogus
+  // "invalid x-api-key" from the API. See src/ssh/sshAuthProxy.ts.
+  if (process.env.ANTHROPIC_UNIX_SOCKET) {
+    return !!process.env.CLAUDE_CODE_OAUTH_TOKEN
+  }
+
+  const is3P =
+    isEnvTruthy(process.env.CLAUDE_CODE_USE_BEDROCK) ||
+    isEnvTruthy(process.env.CLAUDE_CODE_USE_VERTEX) ||
+    isEnvTruthy(process.env.CLAUDE_CODE_USE_FOUNDRY)
+
+  // Check if user has configured an external API key source
+  // This allows externally-provided API keys to work (without requiring proxy configuration)
+  const settings = getSettings_DEPRECATED() || {}
+  const apiKeyHelper = settings.apiKeyHelper
+  const hasExternalAuthToken =
+    process.env.ANTHROPIC_AUTH_TOKEN ||
+    apiKeyHelper ||
+    process.env.CLAUDE_CODE_API_KEY_FILE_DESCRIPTOR
+
+  // Check if API key is from an external source (not managed by /login)
+  const { source: apiKeySource } = getAnthropicApiKeyWithSource({
+    skipRetrievingKeyFromApiKeyHelper: true,
+  })
+  const hasExternalApiKey =
+    apiKeySource === 'ANTHROPIC_API_KEY' || apiKeySource === 'apiKeyHelper'
+
+  // Disable Anthropic auth if:
+  // 1. Using 3rd party services (Bedrock/Vertex/Foundry)
+  // 2. User has an external API key (regardless of proxy configuration)
+  // 3. User has an external auth token (regardless of proxy configuration)
+  // this may cause issues if users have complex proxy / gateway "client-side creds" auth scenarios,
+  // e.g. if they want to set X-Api-Key to a gateway key but use Anthropic OAuth for the Authorization
+  // if we get reports of that, we should probably add an env var to force OAuth enablement
+  const shouldDisableAuth =
+    is3P ||
+    (hasExternalAuthToken && !isManagedOAuthContext()) ||
+    (hasExternalApiKey && !isManagedOAuthContext())
+
+  return !shouldDisableAuth
+}
+
+/** Where the auth token is being sourced from, if any. */
+// this code is closely related to isAnthropicAuthEnabled
+export function getAuthTokenSource() {
+  // --bare: API-key-only. apiKeyHelper (from --settings) is the only
+  // bearer-token-shaped source allowed. OAuth env vars, FD tokens, and
+  // keychain are ignored.
+  if (isBareMode()) {
+    if (getConfiguredApiKeyHelper()) {
+      return { source: 'apiKeyHelper' as const, hasToken: true }
+    }
+    return { source: 'none' as const, hasToken: false }
+  }
+
+  if (process.env.ANTHROPIC_AUTH_TOKEN && !isManagedOAuthContext()) {
+    return { source: 'ANTHROPIC_AUTH_TOKEN' as const, hasToken: true }
+  }
+
+  if (process.env.CLAUDE_CODE_OAUTH_TOKEN) {
+    return { source: 'CLAUDE_CODE_OAUTH_TOKEN' as const, hasToken: true }
+  }
+
+  // Check for OAuth token from file descriptor (or its CCR disk fallback)
+  const oauthTokenFromFd = getOAuthTokenFromFileDescriptor()
+  if (oauthTokenFromFd) {
+    // getOAuthTokenFromFileDescriptor has a disk fallback for CCR subprocesses
+    // that can't inherit the pipe FD. Distinguish by env var presence so the
+    // org-mismatch message doesn't tell the user to unset a variable that
+    // doesn't exist. Call sites fall through correctly — the new source is
+    // !== 'none' (cli/handlers/auth.ts → oauth_token) and not in the
+    // isEnvVarToken set (auth.ts:1844 → generic re-login message).
+    if (process.env.CLAUDE_CODE_OAUTH_TOKEN_FILE_DESCRIPTOR) {
+      return {
+        source: 'CLAUDE_CODE_OAUTH_TOKEN_FILE_DESCRIPTOR' as const,
+        hasToken: true,
+      }
+    }
+    return {
+      source: 'CCR_OAUTH_TOKEN_FILE' as const,
+      hasToken: true,
+    }
+  }
+
+  // Check if apiKeyHelper is configured without executing it
+  // This prevents security issues where arbitrary code could execute before trust is established
+  const apiKeyHelper = getConfiguredApiKeyHelper()
+  if (apiKeyHelper && !isManagedOAuthContext()) {
+    return { source: 'apiKeyHelper' as const, hasToken: true }
+  }
+
+  const oauthTokens = getClaudeAIOAuthTokens()
+  if (shouldUseClaudeAIAuth(oauthTokens?.scopes) && oauthTokens?.accessToken) {
+    return { source: 'claude.ai' as const, hasToken: true }
+  }
+
+  return { source: 'none' as const, hasToken: false }
+}
+
+export type ApiKeySource =
+  | 'ANTHROPIC_API_KEY'
+  | 'apiKeyHelper'
+  | '/login managed key'
+  | 'none'
+
+export function getAnthropicApiKey(): null | string {
+  const { key } = getAnthropicApiKeyWithSource()
+  return key
+}
+
+export function hasAnthropicApiKeyAuth(): boolean {
+  const { key, source } = getAnthropicApiKeyWithSource({
+    skipRetrievingKeyFromApiKeyHelper: true,
+  })
+  return key !== null && source !== 'none'
+}
+
+export function getAnthropicApiKeyWithSource(
+  opts: { skipRetrievingKeyFromApiKeyHelper?: boolean } = {},
+): {
+  key: null | string
+  source: ApiKeySource
+} {
+  const geminiApiKeyEnv = process.env.GEMINI_API_KEY || process.env.GOOGLE_API_KEY
+
+  // --bare: hermetic auth. Only ANTHROPIC_API_KEY env or apiKeyHelper from
+  // the --settings flag. Never touches keychain, config file, or approval
+  // lists. 3P (Bedrock/Vertex/Foundry) uses provider creds, not this path.
+  if (isBareMode()) {
+    if (geminiApiKeyEnv) {
+      return { key: geminiApiKeyEnv, source: 'ANTHROPIC_API_KEY' }
+    }
+    if (getConfiguredApiKeyHelper()) {
+      return {
+        key: opts.skipRetrievingKeyFromApiKeyHelper
+          ? null
+          : getApiKeyFromApiKeyHelperCached(),
+        source: 'apiKeyHelper',
+      }
+    }
+    return { key: null, source: 'none' }
+  }
+
+  // On homespace, don't use ANTHROPIC_API_KEY (use Console key instead)
+  // https://anthropic.slack.com/archives/C08428WSLKV/p1747331773214779
+  const apiKeyEnv = isRunningOnHomespace()
+    ? undefined
+    : geminiApiKeyEnv
+
+  // Always check for direct environment variable when the user ran claude --print.
+  // This is useful for CI, etc.
+  if (preferThirdPartyAuthentication() && apiKeyEnv) {
+    return {
+      key: apiKeyEnv,
+      source: 'ANTHROPIC_API_KEY',
+    }
+  }
+
+  if (isEnvTruthy(process.env.CI) || process.env.NODE_ENV === 'test') {
+    // Check for API key from file descriptor first
+    const apiKeyFromFd = getApiKeyFromFileDescriptor()
+    if (apiKeyFromFd) {
+      return {
+        key: apiKeyFromFd,
+        source: 'ANTHROPIC_API_KEY',
+      }
+    }
+
+    if (
+      !apiKeyEnv &&
+      !process.env.CLAUDE_CODE_OAUTH_TOKEN &&
+      !process.env.CLAUDE_CODE_OAUTH_TOKEN_FILE_DESCRIPTOR
+    ) {
+      throw new Error(
+        'GEMINI_API_KEY or GOOGLE_API_KEY env var is required',
+      )
+    }
+
+    if (apiKeyEnv) {
+      return {
+        key: apiKeyEnv,
+        source: 'ANTHROPIC_API_KEY',
+      }
+    }
+
+    // OAuth token is present but this function returns API keys only
+    return {
+      key: null,
+      source: 'none',
+    }
+  }
+  // Check for ANTHROPIC_API_KEY before checking the apiKeyHelper or /login-managed key
+  if (
+    apiKeyEnv &&
+    getGlobalConfig().customApiKeyResponses?.approved?.includes(
+      normalizeApiKeyForConfig(apiKeyEnv),
+    )
+  ) {
+    return {
+      key: apiKeyEnv,
+      source: 'ANTHROPIC_API_KEY',
+    }
+  }
+
+  // Check for API key from file descriptor
+  const apiKeyFromFd = getApiKeyFromFileDescriptor()
+  if (apiKeyFromFd) {
+    return {
+      key: apiKeyFromFd,
+      source: 'ANTHROPIC_API_KEY',
+    }
+  }
+
+  // Check for apiKeyHelper — use sync cache, never block
+  const apiKeyHelperCommand = getConfiguredApiKeyHelper()
+  if (apiKeyHelperCommand) {
+    if (opts.skipRetrievingKeyFromApiKeyHelper) {
+      return {
+        key: null,
+        source: 'apiKeyHelper',
+      }
+    }
+    // Cache may be cold (helper hasn't finished yet). Return null with
+    // source='apiKeyHelper' rather than falling through to keychain —
+    // apiKeyHelper must win. Callers needing a real key must await
+    // getApiKeyFromApiKeyHelper() first (client.ts, useApiKeyVerification do).
+    return {
+      key: getApiKeyFromApiKeyHelperCached(),
+      source: 'apiKeyHelper',
+    }
+  }
+
+  const apiKeyFromConfigOrMacOSKeychain = getApiKeyFromConfigOrMacOSKeychain()
+  if (apiKeyFromConfigOrMacOSKeychain) {
+    return apiKeyFromConfigOrMacOSKeychain
+  }
+
+  return {
+    key: null,
+    source: 'none',
+  }
+}
+
+/**
+ * Get the configured apiKeyHelper from settings.
+ * In bare mode, only the --settings flag source is consulted — apiKeyHelper
+ * from ~/.claude/settings.json or project settings is ignored.
+ */
+export function getConfiguredApiKeyHelper(): string | undefined {
+  if (isBareMode()) {
+    return getSettingsForSource('flagSettings')?.apiKeyHelper
+  }
+  const mergedSettings = getSettings_DEPRECATED() || {}
+  return mergedSettings.apiKeyHelper
+}
+
+/**
+ * Check if the configured apiKeyHelper comes from project settings (projectSettings or localSettings)
+ */
+function isApiKeyHelperFromProjectOrLocalSettings(): boolean {
+  const apiKeyHelper = getConfiguredApiKeyHelper()
+  if (!apiKeyHelper) {
+    return false
+  }
+
+  const projectSettings = getSettingsForSource('projectSettings')
+  const localSettings = getSettingsForSource('localSettings')
+  return (
+    projectSettings?.apiKeyHelper === apiKeyHelper ||
+    localSettings?.apiKeyHelper === apiKeyHelper
+  )
+}
+
+/**
+ * Get the configured awsAuthRefresh from settings
+ */
+function getConfiguredAwsAuthRefresh(): string | undefined {
+  const mergedSettings = getSettings_DEPRECATED() || {}
+  return mergedSettings.awsAuthRefresh
+}
+
+/**
+ * Check if the configured awsAuthRefresh comes from project settings
+ */
+export function isAwsAuthRefreshFromProjectSettings(): boolean {
+  const awsAuthRefresh = getConfiguredAwsAuthRefresh()
+  if (!awsAuthRefresh) {
+    return false
+  }
+
+  const projectSettings = getSettingsForSource('projectSettings')
+  const localSettings = getSettingsForSource('localSettings')
+  return (
+    projectSettings?.awsAuthRefresh === awsAuthRefresh ||
+    localSettings?.awsAuthRefresh === awsAuthRefresh
+  )
+}
+
+/**
+ * Get the configured awsCredentialExport from settings
+ */
+function getConfiguredAwsCredentialExport(): string | undefined {
+  const mergedSettings = getSettings_DEPRECATED() || {}
+  return mergedSettings.awsCredentialExport
+}
+
+/**
+ * Check if the configured awsCredentialExport comes from project settings
+ */
+export function isAwsCredentialExportFromProjectSettings(): boolean {
+  const awsCredentialExport = getConfiguredAwsCredentialExport()
+  if (!awsCredentialExport) {
+    return false
+  }
+
+  const projectSettings = getSettingsForSource('projectSettings')
+  const localSettings = getSettingsForSource('localSettings')
+  return (
+    projectSettings?.awsCredentialExport === awsCredentialExport ||
+    localSettings?.awsCredentialExport === awsCredentialExport
+  )
+}
+
+/**
+ * Calculate TTL in milliseconds for the API key helper cache
+ * Uses CLAUDE_CODE_API_KEY_HELPER_TTL_MS env var if set and valid,
+ * otherwise defaults to 5 minutes
+ */
+export function calculateApiKeyHelperTTL(): number {
+  const envTtl = process.env.CLAUDE_CODE_API_KEY_HELPER_TTL_MS
+
+  if (envTtl) {
+    const parsed = parseInt(envTtl, 10)
+    if (!Number.isNaN(parsed) && parsed >= 0) {
+      return parsed
+    }
+    logForDebugging(
+      `Found CLAUDE_CODE_API_KEY_HELPER_TTL_MS env var, but it was not a valid number. Got ${envTtl}`,
+      { level: 'error' },
+    )
+  }
+
+  return DEFAULT_API_KEY_HELPER_TTL
+}
+
+// Async API key helper with sync cache for non-blocking reads.
+// Epoch bumps on clearApiKeyHelperCache() — orphaned executions check their
+// captured epoch before touching module state so a settings-change or 401-retry
+// mid-flight can't clobber the newer cache/inflight.
+let _apiKeyHelperCache: { value: string; timestamp: number } | null = null
+let _apiKeyHelperInflight: {
+  promise: Promise<string | null>
+  // Only set on cold launches (user is waiting); null for SWR background refreshes.
+  startedAt: number | null
+} | null = null
+let _apiKeyHelperEpoch = 0
+
+export function getApiKeyHelperElapsedMs(): number {
+  const startedAt = _apiKeyHelperInflight?.startedAt
+  return startedAt ? Date.now() - startedAt : 0
+}
+
+export async function getApiKeyFromApiKeyHelper(
+  isNonInteractiveSession: boolean,
+): Promise<string | null> {
+  if (!getConfiguredApiKeyHelper()) return null
+  const ttl = calculateApiKeyHelperTTL()
+  if (_apiKeyHelperCache) {
+    if (Date.now() - _apiKeyHelperCache.timestamp < ttl) {
+      return _apiKeyHelperCache.value
+    }
+    // Stale — return stale value now, refresh in the background.
+    // `??=` banned here by eslint no-nullish-assign-object-call (bun bug).
+    if (!_apiKeyHelperInflight) {
+      _apiKeyHelperInflight = {
+        promise: _runAndCache(
+          isNonInteractiveSession,
+          false,
+          _apiKeyHelperEpoch,
+        ),
+        startedAt: null,
+      }
+    }
+    return _apiKeyHelperCache.value
+  }
+  // Cold cache — deduplicate concurrent calls
+  if (_apiKeyHelperInflight) return _apiKeyHelperInflight.promise
+  _apiKeyHelperInflight = {
+    promise: _runAndCache(isNonInteractiveSession, true, _apiKeyHelperEpoch),
+    startedAt: Date.now(),
+  }
+  return _apiKeyHelperInflight.promise
+}
+
+async function _runAndCache(
+  isNonInteractiveSession: boolean,
+  isCold: boolean,
+  epoch: number,
+): Promise<string | null> {
+  try {
+    const value = await _executeApiKeyHelper(isNonInteractiveSession)
+    if (epoch !== _apiKeyHelperEpoch) return value
+    if (value !== null) {
+      _apiKeyHelperCache = { value, timestamp: Date.now() }
+    }
+    return value
+  } catch (e) {
+    if (epoch !== _apiKeyHelperEpoch) return ' '
+    const detail = e instanceof Error ? e.message : String(e)
+    // biome-ignore lint/suspicious/noConsole: user-configured script failed; must be visible without --debug
+    console.error(chalk.red(`apiKeyHelper failed: ${detail}`))
+    logForDebugging(`Error getting API key from apiKeyHelper: ${detail}`, {
+      level: 'error',
+    })
+    // SWR path: a transient failure shouldn't replace a working key with
+    // the ' ' sentinel — keep serving the stale value and bump timestamp
+    // so we don't hammer-retry every call.
+    if (!isCold && _apiKeyHelperCache && _apiKeyHelperCache.value !== ' ') {
+      _apiKeyHelperCache = { ..._apiKeyHelperCache, timestamp: Date.now() }
+      return _apiKeyHelperCache.value
+    }
+    // Cold cache or prior error — cache ' ' so callers don't fall back to OAuth
+    _apiKeyHelperCache = { value: ' ', timestamp: Date.now() }
+    return ' '
+  } finally {
+    if (epoch === _apiKeyHelperEpoch) {
+      _apiKeyHelperInflight = null
+    }
+  }
+}
+
+async function _executeApiKeyHelper(
+  isNonInteractiveSession: boolean,
+): Promise<string | null> {
+  const apiKeyHelper = getConfiguredApiKeyHelper()
+  if (!apiKeyHelper) {
+    return null
+  }
+
+  if (isApiKeyHelperFromProjectOrLocalSettings()) {
+    const hasTrust = checkHasTrustDialogAccepted()
+    if (!hasTrust && !isNonInteractiveSession) {
+      const error = new Error(
+        `Security: apiKeyHelper executed before workspace trust is confirmed. If you see this message, post in ${MACRO.FEEDBACK_CHANNEL}.`,
+      )
+      logAntError('apiKeyHelper invoked before trust check', error)
+      logEvent('tengu_apiKeyHelper_missing_trust11', {})
+      return null
+    }
+  }
+
+  const result = await execa(apiKeyHelper, {
+    shell: true,
+    timeout: 10 * 60 * 1000,
+    reject: false,
+  })
+  if (result.failed) {
+    // reject:false — execa resolves on exit≠0/timeout, stderr is on result
+    const why = result.timedOut ? 'timed out' : `exited ${result.exitCode}`
+    const stderr = result.stderr?.trim()
+    throw new Error(stderr ? `${why}: ${stderr}` : why)
+  }
+  const stdout = result.stdout?.trim()
+  if (!stdout) {
+    throw new Error('did not return a value')
+  }
+  return stdout
+}
+
+/**
+ * Sync cache reader — returns the last fetched apiKeyHelper value without executing.
+ * Returns stale values to match SWR semantics of the async reader.
+ * Returns null only if the async fetch hasn't completed yet.
+ */
+export function getApiKeyFromApiKeyHelperCached(): string | null {
+  return _apiKeyHelperCache?.value ?? null
+}
+
+export function clearApiKeyHelperCache(): void {
+  _apiKeyHelperEpoch++
+  _apiKeyHelperCache = null
+  _apiKeyHelperInflight = null
+}
+
+export function prefetchApiKeyFromApiKeyHelperIfSafe(
+  isNonInteractiveSession: boolean,
+): void {
+  // Skip if trust not yet accepted — the inner _executeApiKeyHelper check
+  // would catch this too, but would fire a false-positive analytics event.
+  if (
+    isApiKeyHelperFromProjectOrLocalSettings() &&
+    !checkHasTrustDialogAccepted()
+  ) {
+    return
+  }
+  void getApiKeyFromApiKeyHelper(isNonInteractiveSession)
+}
+
+/** Default STS credentials are one hour. We manually manage invalidation, so not too worried about this being accurate. */
+const DEFAULT_AWS_STS_TTL = 60 * 60 * 1000
+
+/**
+ * Run awsAuthRefresh to perform interactive authentication (e.g., aws sso login)
+ * Streams output in real-time for user visibility
+ */
+async function runAwsAuthRefresh(): Promise<boolean> {
+  const awsAuthRefresh = getConfiguredAwsAuthRefresh()
+
+  if (!awsAuthRefresh) {
+    return false // Not configured, treat as success
+  }
+
+  // SECURITY: Check if awsAuthRefresh is from project settings
+  if (isAwsAuthRefreshFromProjectSettings()) {
+    // Check if trust has been established for this project
+    const hasTrust = checkHasTrustDialogAccepted()
+    if (!hasTrust && !getIsNonInteractiveSession()) {
+      const error = new Error(
+        `Security: awsAuthRefresh executed before workspace trust is confirmed. If you see this message, post in ${MACRO.FEEDBACK_CHANNEL}.`,
+      )
+      logAntError('awsAuthRefresh invoked before trust check', error)
+      logEvent('tengu_awsAuthRefresh_missing_trust', {})
+      return false
+    }
+  }
+
+  try {
+    logForDebugging('Fetching AWS caller identity for AWS auth refresh command')
+    await checkStsCallerIdentity()
+    logForDebugging(
+      'Fetched AWS caller identity, skipping AWS auth refresh command',
+    )
+    return false
+  } catch {
+    // only actually do the refresh if caller-identity calls
+    return refreshAwsAuth(awsAuthRefresh)
+  }
+}
+
+// Timeout for AWS auth refresh command (3 minutes).
+// Long enough for browser-based SSO flows, short enough to prevent indefinite hangs.
+const AWS_AUTH_REFRESH_TIMEOUT_MS = 3 * 60 * 1000
+
+export function refreshAwsAuth(awsAuthRefresh: string): Promise<boolean> {
+  logForDebugging('Running AWS auth refresh command')
+  // Start tracking authentication status
+  const authStatusManager = AwsAuthStatusManager.getInstance()
+  authStatusManager.startAuthentication()
+
+  return new Promise(resolve => {
+    const refreshProc = exec(awsAuthRefresh, {
+      timeout: AWS_AUTH_REFRESH_TIMEOUT_MS,
+    })
+    refreshProc.stdout!.on('data', data => {
+      const output = data.toString().trim()
+      if (output) {
+        // Add output to status manager for UI display
+        authStatusManager.addOutput(output)
+        // Also log for debugging
+        logForDebugging(output, { level: 'debug' })
+      }
+    })
+
+    refreshProc.stderr!.on('data', data => {
+      const error = data.toString().trim()
+      if (error) {
+        authStatusManager.setError(error)
+        logForDebugging(error, { level: 'error' })
+      }
+    })
+
+    refreshProc.on('close', (code, signal) => {
+      if (code === 0) {
+        logForDebugging('AWS auth refresh completed successfully')
+        authStatusManager.endAuthentication(true)
+        void resolve(true)
+      } else {
+        const timedOut = signal === 'SIGTERM'
+        const message = timedOut
+          ? chalk.red(
+              'AWS auth refresh timed out after 3 minutes. Run your auth command manually in a separate terminal.',
+            )
+          : chalk.red(
+              'Error running awsAuthRefresh (in settings or ~/.claude.json):',
+            )
+        // biome-ignore lint/suspicious/noConsole:: intentional console output
+        console.error(message)
+        authStatusManager.endAuthentication(false)
+        void resolve(false)
+      }
+    })
+  })
+}
+
+/**
+ * Run awsCredentialExport to get credentials and set environment variables
+ * Expects JSON output containing AWS credentials
+ */
+async function getAwsCredsFromCredentialExport(): Promise<{
+  accessKeyId: string
+  secretAccessKey: string
+  sessionToken: string
+} | null> {
+  const awsCredentialExport = getConfiguredAwsCredentialExport()
+
+  if (!awsCredentialExport) {
+    return null
+  }
+
+  // SECURITY: Check if awsCredentialExport is from project settings
+  if (isAwsCredentialExportFromProjectSettings()) {
+    // Check if trust has been established for this project
+    const hasTrust = checkHasTrustDialogAccepted()
+    if (!hasTrust && !getIsNonInteractiveSession()) {
+      const error = new Error(
+        `Security: awsCredentialExport executed before workspace trust is confirmed. If you see this message, post in ${MACRO.FEEDBACK_CHANNEL}.`,
+      )
+      logAntError('awsCredentialExport invoked before trust check', error)
+      logEvent('tengu_awsCredentialExport_missing_trust', {})
+      return null
+    }
+  }
+
+  try {
+    logForDebugging(
+      'Fetching AWS caller identity for credential export command',
+    )
+    await checkStsCallerIdentity()
+    logForDebugging(
+      'Fetched AWS caller identity, skipping AWS credential export command',
+    )
+    return null
+  } catch {
+    // only actually do the export if caller-identity calls
+    try {
+      logForDebugging('Running AWS credential export command')
+      const result = await execa(awsCredentialExport, {
+        shell: true,
+        reject: false,
+      })
+      if (result.exitCode !== 0 || !result.stdout) {
+        throw new Error('awsCredentialExport did not return a valid value')
+      }
+
+      // Parse the JSON output from aws sts commands
+      const awsOutput = jsonParse(result.stdout.trim())
+
+      if (!isValidAwsStsOutput(awsOutput)) {
+        throw new Error(
+          'awsCredentialExport did not return valid AWS STS output structure',
+        )
+      }
+
+      logForDebugging('AWS credentials retrieved from awsCredentialExport')
+      return {
+        accessKeyId: awsOutput.Credentials.AccessKeyId,
+        secretAccessKey: awsOutput.Credentials.SecretAccessKey,
+        sessionToken: awsOutput.Credentials.SessionToken,
+      }
+    } catch (e) {
+      const message = chalk.red(
+        'Error getting AWS credentials from awsCredentialExport (in settings or ~/.claude.json):',
+      )
+      if (e instanceof Error) {
+        // biome-ignore lint/suspicious/noConsole:: intentional console output
+        console.error(message, e.message)
+      } else {
+        // biome-ignore lint/suspicious/noConsole:: intentional console output
+        console.error(message, e)
+      }
+      return null
+    }
+  }
+}
+
+/**
+ * Refresh AWS authentication and get credentials with cache clearing
+ * This combines runAwsAuthRefresh, getAwsCredsFromCredentialExport, and clearAwsIniCache
+ * to ensure fresh credentials are always used
+ */
+export const refreshAndGetAwsCredentials = memoizeWithTTLAsync(
+  async (): Promise<{
+    accessKeyId: string
+    secretAccessKey: string
+    sessionToken: string
+  } | null> => {
+    // First run auth refresh if needed
+    const refreshed = await runAwsAuthRefresh()
+
+    // Get credentials from export
+    const credentials = await getAwsCredsFromCredentialExport()
+
+    // Clear AWS INI cache to ensure fresh credentials are used
+    if (refreshed || credentials) {
+      await clearAwsIniCache()
+    }
+
+    return credentials
+  },
+  DEFAULT_AWS_STS_TTL,
+)
+
+export function clearAwsCredentialsCache(): void {
+  refreshAndGetAwsCredentials.cache.clear()
+}
+
+/**
+ * Get the configured gcpAuthRefresh from settings
+ */
+function getConfiguredGcpAuthRefresh(): string | undefined {
+  const mergedSettings = getSettings_DEPRECATED() || {}
+  return mergedSettings.gcpAuthRefresh
+}
+
+/**
+ * Check if the configured gcpAuthRefresh comes from project settings
+ */
+export function isGcpAuthRefreshFromProjectSettings(): boolean {
+  const gcpAuthRefresh = getConfiguredGcpAuthRefresh()
+  if (!gcpAuthRefresh) {
+    return false
+  }
+
+  const projectSettings = getSettingsForSource('projectSettings')
+  const localSettings = getSettingsForSource('localSettings')
+  return (
+    projectSettings?.gcpAuthRefresh === gcpAuthRefresh ||
+    localSettings?.gcpAuthRefresh === gcpAuthRefresh
+  )
+}
+
+/** Short timeout for the GCP credentials probe. Without this, when no local
+ *  credential source exists (no ADC file, no env var), google-auth-library falls
+ *  through to the GCE metadata server which hangs ~12s outside GCP. */
+const GCP_CREDENTIALS_CHECK_TIMEOUT_MS = 5_000
+
+/**
+ * Check if GCP credentials are currently valid by attempting to get an access token.
+ * This uses the same authentication chain that the Vertex SDK uses.
+ */
+export async function checkGcpCredentialsValid(): Promise<boolean> {
+  try {
+    // Dynamically import to avoid loading google-auth-library unnecessarily
+    const { GoogleAuth } = await import('google-auth-library')
+    const auth = new GoogleAuth({
+      scopes: ['https://www.googleapis.com/auth/cloud-platform'],
+    })
+    const probe = (async () => {
+      const client = await auth.getClient()
+      await client.getAccessToken()
+    })()
+    const timeout = sleep(GCP_CREDENTIALS_CHECK_TIMEOUT_MS).then(() => {
+      throw new GcpCredentialsTimeoutError('GCP credentials check timed out')
+    })
+    await Promise.race([probe, timeout])
+    return true
+  } catch {
+    return false
+  }
+}
+
+/** Default GCP credential TTL - 1 hour to match typical ADC token lifetime */
+const DEFAULT_GCP_CREDENTIAL_TTL = 60 * 60 * 1000
+
+/**
+ * Run gcpAuthRefresh to perform interactive authentication (e.g., gcloud auth application-default login)
+ * Streams output in real-time for user visibility
+ */
+async function runGcpAuthRefresh(): Promise<boolean> {
+  const gcpAuthRefresh = getConfiguredGcpAuthRefresh()
+
+  if (!gcpAuthRefresh) {
+    return false // Not configured, treat as success
+  }
+
+  // SECURITY: Check if gcpAuthRefresh is from project settings
+  if (isGcpAuthRefreshFromProjectSettings()) {
+    // Check if trust has been established for this project
+    // Pass true to indicate this is a dangerous feature that requires trust
+    const hasTrust = checkHasTrustDialogAccepted()
+    if (!hasTrust && !getIsNonInteractiveSession()) {
+      const error = new Error(
+        `Security: gcpAuthRefresh executed before workspace trust is confirmed. If you see this message, post in ${MACRO.FEEDBACK_CHANNEL}.`,
+      )
+      logAntError('gcpAuthRefresh invoked before trust check', error)
+      logEvent('tengu_gcpAuthRefresh_missing_trust', {})
+      return false
+    }
+  }
+
+  try {
+    logForDebugging('Checking GCP credentials validity for auth refresh')
+    const isValid = await checkGcpCredentialsValid()
+    if (isValid) {
+      logForDebugging(
+        'GCP credentials are valid, skipping auth refresh command',
+      )
+      return false
+    }
+  } catch {
+    // Credentials check failed, proceed with refresh
+  }
+
+  return refreshGcpAuth(gcpAuthRefresh)
+}
+
+// Timeout for GCP auth refresh command (3 minutes).
+// Long enough for browser-based auth flows, short enough to prevent indefinite hangs.
+const GCP_AUTH_REFRESH_TIMEOUT_MS = 3 * 60 * 1000
+
+export function refreshGcpAuth(gcpAuthRefresh: string): Promise<boolean> {
+  logForDebugging('Running GCP auth refresh command')
+  // Start tracking authentication status. AwsAuthStatusManager is cloud-provider-agnostic
+  // despite the name — print.ts emits its updates as generic SDK 'auth_status' messages.
+  const authStatusManager = AwsAuthStatusManager.getInstance()
+  authStatusManager.startAuthentication()
+
+  return new Promise(resolve => {
+    const refreshProc = exec(gcpAuthRefresh, {
+      timeout: GCP_AUTH_REFRESH_TIMEOUT_MS,
+    })
+    refreshProc.stdout!.on('data', data => {
+      const output = data.toString().trim()
+      if (output) {
+        // Add output to status manager for UI display
+        authStatusManager.addOutput(output)
+        // Also log for debugging
+        logForDebugging(output, { level: 'debug' })
+      }
+    })
+
+    refreshProc.stderr!.on('data', data => {
+      const error = data.toString().trim()
+      if (error) {
+        authStatusManager.setError(error)
+        logForDebugging(error, { level: 'error' })
+      }
+    })
+
+    refreshProc.on('close', (code, signal) => {
+      if (code === 0) {
+        logForDebugging('GCP auth refresh completed successfully')
+        authStatusManager.endAuthentication(true)
+        void resolve(true)
+      } else {
+        const timedOut = signal === 'SIGTERM'
+        const message = timedOut
+          ? chalk.red(
+              'GCP auth refresh timed out after 3 minutes. Run your auth command manually in a separate terminal.',
+            )
+          : chalk.red(
+              'Error running gcpAuthRefresh (in settings or ~/.claude.json):',
+            )
+        // biome-ignore lint/suspicious/noConsole:: intentional console output
+        console.error(message)
+        authStatusManager.endAuthentication(false)
+        void resolve(false)
+      }
+    })
+  })
+}
+
+/**
+ * Refresh GCP authentication if needed.
+ * This function checks if credentials are valid and runs the refresh command if not.
+ * Memoized with TTL to avoid excessive refresh attempts.
+ */
+export const refreshGcpCredentialsIfNeeded = memoizeWithTTLAsync(
+  async (): Promise<boolean> => {
+    // Run auth refresh if needed
+    const refreshed = await runGcpAuthRefresh()
+    return refreshed
+  },
+  DEFAULT_GCP_CREDENTIAL_TTL,
+)
+
+export function clearGcpCredentialsCache(): void {
+  refreshGcpCredentialsIfNeeded.cache.clear()
+}
+
+/**
+ * Prefetches GCP credentials only if workspace trust has already been established.
+ * This allows us to start the potentially slow GCP commands early for trusted workspaces
+ * while maintaining security for untrusted ones.
+ *
+ * Returns void to prevent misuse - use refreshGcpCredentialsIfNeeded() to actually refresh.
+ */
+export function prefetchGcpCredentialsIfSafe(): void {
+  // Check if gcpAuthRefresh is configured
+  const gcpAuthRefresh = getConfiguredGcpAuthRefresh()
+
+  if (!gcpAuthRefresh) {
+    return
+  }
+
+  // Check if gcpAuthRefresh is from project settings
+  if (isGcpAuthRefreshFromProjectSettings()) {
+    // Only prefetch if trust has already been established
+    const hasTrust = checkHasTrustDialogAccepted()
+    if (!hasTrust && !getIsNonInteractiveSession()) {
+      // Don't prefetch - wait for trust to be established first
+      return
+    }
+  }
+
+  // Safe to prefetch - either not from project settings or trust already established
+  void refreshGcpCredentialsIfNeeded()
+}
+
+/**
+ * Prefetches AWS credentials only if workspace trust has already been established.
+ * This allows us to start the potentially slow AWS commands early for trusted workspaces
+ * while maintaining security for untrusted ones.
+ *
+ * Returns void to prevent misuse - use refreshAndGetAwsCredentials() to actually retrieve credentials.
+ */
+export function prefetchAwsCredentialsAndBedRockInfoIfSafe(): void {
+  // Check if either AWS command is configured
+  const awsAuthRefresh = getConfiguredAwsAuthRefresh()
+  const awsCredentialExport = getConfiguredAwsCredentialExport()
+
+  if (!awsAuthRefresh && !awsCredentialExport) {
+    return
+  }
+
+  // Check if either command is from project settings
+  if (
+    isAwsAuthRefreshFromProjectSettings() ||
+    isAwsCredentialExportFromProjectSettings()
+  ) {
+    // Only prefetch if trust has already been established
+    const hasTrust = checkHasTrustDialogAccepted()
+    if (!hasTrust && !getIsNonInteractiveSession()) {
+      // Don't prefetch - wait for trust to be established first
+      return
+    }
+  }
+
+  // Safe to prefetch - either not from project settings or trust already established
+  void refreshAndGetAwsCredentials()
+  getModelStrings()
+}
+
+/** @private Use {@link getAnthropicApiKey} or {@link getAnthropicApiKeyWithSource} */
+export const getApiKeyFromConfigOrMacOSKeychain = memoize(
+  (): { key: string; source: ApiKeySource } | null => {
+    if (isBareMode()) return null
+    // TODO: migrate to SecureStorage
+    if (process.platform === 'darwin') {
+      // keychainPrefetch.ts fires this read at main.tsx top-level in parallel
+      // with module imports. If it completed, use that instead of spawning a
+      // sync `security` subprocess here (~33ms).
+      const prefetch = getLegacyApiKeyPrefetchResult()
+      if (prefetch) {
+        if (prefetch.stdout) {
+          return { key: prefetch.stdout, source: '/login managed key' }
+        }
+        // Prefetch completed with no key — fall through to config, not keychain.
+      } else {
+        const storageServiceName = getMacOsKeychainStorageServiceName()
+        try {
+          const result = execSyncWithDefaults_DEPRECATED(
+            `security find-generic-password -a $USER -w -s "${storageServiceName}"`,
+          )
+          if (result) {
+            return { key: result, source: '/login managed key' }
+          }
+        } catch (e) {
+          logError(e)
+        }
+      }
+    }
+
+    const config = getGlobalConfig()
+    if (!config.primaryApiKey) {
+      return null
+    }
+
+    return { key: config.primaryApiKey, source: '/login managed key' }
+  },
+)
+
+function isValidApiKey(apiKey: string): boolean {
+  // Only allow alphanumeric characters, dashes, and underscores
+  return /^[a-zA-Z0-9-_]+$/.test(apiKey)
+}
+
+export async function saveApiKey(apiKey: string): Promise<void> {
+  if (!isValidApiKey(apiKey)) {
+    throw new Error(
+      'Invalid API key format. API key must contain only alphanumeric characters, dashes, and underscores.',
+    )
+  }
+
+  // Store as primary API key
+  await maybeRemoveApiKeyFromMacOSKeychain()
+  let savedToKeychain = false
+  if (process.platform === 'darwin') {
+    try {
+      // TODO: migrate to SecureStorage
+      const storageServiceName = getMacOsKeychainStorageServiceName()
+      const username = getUsername()
+
+      // Convert to hexadecimal to avoid any escaping issues
+      const hexValue = Buffer.from(apiKey, 'utf-8').toString('hex')
+
+      // Use security's interactive mode (-i) with -X (hexadecimal) option
+      // This ensures credentials never appear in process command-line arguments
+      // Process monitors only see "security -i", not the password
+      const command = `add-generic-password -U -a "${username}" -s "${storageServiceName}" -X "${hexValue}"\n`
+
+      await execa('security', ['-i'], {
+        input: command,
+        reject: false,
+      })
+
+      logEvent('tengu_api_key_saved_to_keychain', {})
+      savedToKeychain = true
+    } catch (e) {
+      logError(e)
+      logEvent('tengu_api_key_keychain_error', {
+        error: errorMessage(
+          e,
+        ) as AnalyticsMetadata_I_VERIFIED_THIS_IS_NOT_CODE_OR_FILEPATHS,
+      })
+      logEvent('tengu_api_key_saved_to_config', {})
+    }
+  } else {
+    logEvent('tengu_api_key_saved_to_config', {})
+  }
+
+  const normalizedKey = normalizeApiKeyForConfig(apiKey)
+
+  // Save config with all updates
+  saveGlobalConfig(current => {
+    const approved = current.customApiKeyResponses?.approved ?? []
+    return {
+      ...current,
+      // Only save to config if keychain save failed or not on darwin
+      primaryApiKey: savedToKeychain ? current.primaryApiKey : apiKey,
+      customApiKeyResponses: {
+        ...current.customApiKeyResponses,
+        approved: approved.includes(normalizedKey)
+          ? approved
+          : [...approved, normalizedKey],
+        rejected: current.customApiKeyResponses?.rejected ?? [],
+      },
+    }
+  })
+
+  // Clear memo cache
+  getApiKeyFromConfigOrMacOSKeychain.cache.clear?.()
+  clearLegacyApiKeyPrefetch()
+}
+
+export function isCustomApiKeyApproved(apiKey: string): boolean {
+  const config = getGlobalConfig()
+  const normalizedKey = normalizeApiKeyForConfig(apiKey)
+  return (
+    config.customApiKeyResponses?.approved?.includes(normalizedKey) ?? false
+  )
+}
+
+export async function removeApiKey(): Promise<void> {
+  await maybeRemoveApiKeyFromMacOSKeychain()
+
+  // Also remove from config instead of returning early, for older clients
+  // that set keys before we supported keychain.
+  saveGlobalConfig(current => ({
+    ...current,
+    primaryApiKey: undefined,
+  }))
+
+  // Clear memo cache
+  getApiKeyFromConfigOrMacOSKeychain.cache.clear?.()
+  clearLegacyApiKeyPrefetch()
+}
+
+async function maybeRemoveApiKeyFromMacOSKeychain(): Promise<void> {
+  try {
+    await maybeRemoveApiKeyFromMacOSKeychainThrows()
+  } catch (e) {
+    logError(e)
+  }
+}
+
+// Function to store OAuth tokens in secure storage
+export function saveOAuthTokensIfNeeded(tokens: OAuthTokens): {
+  success: boolean
+  warning?: string
+} {
+  if (!shouldUseClaudeAIAuth(tokens.scopes)) {
+    logEvent('tengu_oauth_tokens_not_claude_ai', {})
+    return { success: true }
+  }
+
+  // Skip saving inference-only tokens (they come from env vars)
+  if (!tokens.refreshToken || !tokens.expiresAt) {
+    logEvent('tengu_oauth_tokens_inference_only', {})
+    return { success: true }
+  }
+
+  const secureStorage = getSecureStorage()
+  const storageBackend =
+    secureStorage.name as AnalyticsMetadata_I_VERIFIED_THIS_IS_NOT_CODE_OR_FILEPATHS
+
+  try {
+    const storageData = secureStorage.read() || {}
+    const existingOauth = storageData.claudeAiOauth
+
+    storageData.claudeAiOauth = {
+      accessToken: tokens.accessToken,
+      refreshToken: tokens.refreshToken,
+      expiresAt: tokens.expiresAt,
+      scopes: tokens.scopes,
+      // Profile fetch in refreshOAuthToken swallows errors and returns null on
+      // transient failures (network, 5xx, rate limit). Don't clobber a valid
+      // stored subscription with null — fall back to the existing value.
+      subscriptionType:
+        tokens.subscriptionType ?? existingOauth?.subscriptionType ?? null,
+      rateLimitTier:
+        tokens.rateLimitTier ?? existingOauth?.rateLimitTier ?? null,
+    }
+
+    const updateStatus = secureStorage.update(storageData)
+
+    if (updateStatus.success) {
+      logEvent('tengu_oauth_tokens_saved', { storageBackend })
+    } else {
+      logEvent('tengu_oauth_tokens_save_failed', { storageBackend })
+    }
+
+    getClaudeAIOAuthTokens.cache?.clear?.()
+    clearBetasCaches()
+    clearToolSchemaCache()
+    return updateStatus
+  } catch (error) {
+    logError(error)
+    logEvent('tengu_oauth_tokens_save_exception', {
+      storageBackend,
+      error: errorMessage(
+        error,
+      ) as AnalyticsMetadata_I_VERIFIED_THIS_IS_NOT_CODE_OR_FILEPATHS,
+    })
+    return { success: false, warning: 'Failed to save OAuth tokens' }
+  }
+}
+
+export const getClaudeAIOAuthTokens = memoize((): OAuthTokens | null => {
+  // --bare: API-key-only. No OAuth env tokens, no keychain, no credentials file.
+  if (isBareMode()) return null
+
+  // Check for force-set OAuth token from environment variable
+  if (process.env.CLAUDE_CODE_OAUTH_TOKEN) {
+    // Return an inference-only token (unknown refresh and expiry)
+    return {
+      accessToken: process.env.CLAUDE_CODE_OAUTH_TOKEN,
+      refreshToken: null,
+      expiresAt: null,
+      scopes: ['user:inference'],
+      subscriptionType: null,
+      rateLimitTier: null,
+    }
+  }
+
+  // Check for OAuth token from file descriptor
+  const oauthTokenFromFd = getOAuthTokenFromFileDescriptor()
+  if (oauthTokenFromFd) {
+    // Return an inference-only token (unknown refresh and expiry)
+    return {
+      accessToken: oauthTokenFromFd,
+      refreshToken: null,
+      expiresAt: null,
+      scopes: ['user:inference'],
+      subscriptionType: null,
+      rateLimitTier: null,
+    }
+  }
+
+  try {
+    const secureStorage = getSecureStorage()
+    const storageData = secureStorage.read()
+    const oauthData = storageData?.claudeAiOauth
+
+    if (!oauthData?.accessToken) {
+      return null
+    }
+
+    return oauthData
+  } catch (error) {
+    logError(error)
+    return null
+  }
+})
+
+/**
+ * Clears all OAuth token caches. Call this on 401 errors to ensure
+ * the next token read comes from secure storage, not stale in-memory caches.
+ * This handles the case where the local expiration check disagrees with the
+ * server (e.g., due to clock corrections after token was issued).
+ */
+export function clearOAuthTokenCache(): void {
+  getClaudeAIOAuthTokens.cache?.clear?.()
+  clearKeychainCache()
+}
+
+let lastCredentialsMtimeMs = 0
+
+// Cross-process staleness: another CC instance may write fresh tokens to
+// disk (refresh or /login), but this process's memoize caches forever.
+// Without this, terminal 1's /login fixes terminal 1; terminal 2's /login
+// then revokes terminal 1 server-side, and terminal 1's memoize never
+// re-reads — infinite /login regress (CC-1096, GH#24317).
+async function invalidateOAuthCacheIfDiskChanged(): Promise<void> {
+  try {
+    const { mtimeMs } = await stat(
+      join(getClaudeConfigHomeDir(), '.credentials.json'),
+    )
+    if (mtimeMs !== lastCredentialsMtimeMs) {
+      lastCredentialsMtimeMs = mtimeMs
+      clearOAuthTokenCache()
+    }
+  } catch {
+    // ENOENT — macOS keychain path (file deleted on migration). Clear only
+    // the memoize so it delegates to the keychain cache's 30s TTL instead
+    // of caching forever on top. `security find-generic-password` is
+    // ~15ms; bounded to once per 30s by the keychain cache.
+    getClaudeAIOAuthTokens.cache?.clear?.()
+  }
+}
+
+// In-flight dedup: when N claude.ai proxy connectors hit 401 with the same
+// token simultaneously (common at startup — #20930), only one should clear
+// caches and re-read the keychain. Without this, each call's clearOAuthTokenCache()
+// nukes readInFlight in macOsKeychainStorage and triggers a fresh spawn —
+// sync spawns stacked to 800ms+ of blocked render frames.
+const pending401Handlers = new Map<string, Promise<boolean>>()
+
+/**
+ * Handle a 401 "OAuth token has expired" error from the API.
+ *
+ * This function forces a token refresh when the server says the token is expired,
+ * even if our local expiration check disagrees (which can happen due to clock
+ * issues when the token was issued).
+ *
+ * Safety: We compare the failed token with what's in keychain. If another tab
+ * already refreshed (different token in keychain), we use that instead of
+ * refreshing again. Concurrent calls with the same failedAccessToken are
+ * deduplicated to a single keychain read.
+ *
+ * @param failedAccessToken - The access token that was rejected with 401
+ * @returns true if we now have a valid token, false otherwise
+ */
+export function handleOAuth401Error(
+  failedAccessToken: string,
+): Promise<boolean> {
+  const pending = pending401Handlers.get(failedAccessToken)
+  if (pending) return pending
+
+  const promise = handleOAuth401ErrorImpl(failedAccessToken).finally(() => {
+    pending401Handlers.delete(failedAccessToken)
+  })
+  pending401Handlers.set(failedAccessToken, promise)
+  return promise
+}
+
+async function handleOAuth401ErrorImpl(
+  failedAccessToken: string,
+): Promise<boolean> {
+  // Clear caches and re-read from keychain (async — sync read blocks ~100ms/call)
+  clearOAuthTokenCache()
+  const currentTokens = await getClaudeAIOAuthTokensAsync()
+
+  if (!currentTokens?.refreshToken) {
+    return false
+  }
+
+  // If keychain has a different token, another tab already refreshed - use it
+  if (currentTokens.accessToken !== failedAccessToken) {
+    logEvent('tengu_oauth_401_recovered_from_keychain', {})
+    return true
+  }
+
+  // Same token that failed - force refresh, bypassing local expiration check
+  return checkAndRefreshOAuthTokenIfNeeded(0, true)
+}
+
+/**
+ * Reads OAuth tokens asynchronously, avoiding blocking keychain reads.
+ * Delegates to the sync memoized version for env var / file descriptor tokens
+ * (which don't hit the keychain), and only uses async for storage reads.
+ */
+export async function getClaudeAIOAuthTokensAsync(): Promise<OAuthTokens | null> {
+  if (isBareMode()) return null
+
+  // Env var and FD tokens are sync and don't hit the keychain
+  if (
+    process.env.CLAUDE_CODE_OAUTH_TOKEN ||
+    getOAuthTokenFromFileDescriptor()
+  ) {
+    return getClaudeAIOAuthTokens()
+  }
+
+  try {
+    const secureStorage = getSecureStorage()
+    const storageData = await secureStorage.readAsync()
+    const oauthData = storageData?.claudeAiOauth
+    if (!oauthData?.accessToken) {
+      return null
+    }
+    return oauthData
+  } catch (error) {
+    logError(error)
+    return null
+  }
+}
+
+// In-flight promise for deduplicating concurrent calls
+let pendingRefreshCheck: Promise<boolean> | null = null
+
+export function checkAndRefreshOAuthTokenIfNeeded(
+  retryCount = 0,
+  force = false,
+): Promise<boolean> {
+  // Deduplicate concurrent non-retry, non-force calls
+  if (retryCount === 0 && !force) {
+    if (pendingRefreshCheck) {
+      return pendingRefreshCheck
+    }
+
+    const promise = checkAndRefreshOAuthTokenIfNeededImpl(retryCount, force)
+    pendingRefreshCheck = promise.finally(() => {
+      pendingRefreshCheck = null
+    })
+    return pendingRefreshCheck
+  }
+
+  return checkAndRefreshOAuthTokenIfNeededImpl(retryCount, force)
+}
+
+async function checkAndRefreshOAuthTokenIfNeededImpl(
+  retryCount: number,
+  force: boolean,
+): Promise<boolean> {
+  const MAX_RETRIES = 5
+
+  await invalidateOAuthCacheIfDiskChanged()
+
+  // First check if token is expired with cached value
+  // Skip this check if force=true (server already told us token is bad)
+  const tokens = getClaudeAIOAuthTokens()
+  if (!force) {
+    if (!tokens?.refreshToken || !isOAuthTokenExpired(tokens.expiresAt)) {
+      return false
+    }
+  }
+
+  if (!tokens?.refreshToken) {
+    return false
+  }
+
+  if (!shouldUseClaudeAIAuth(tokens.scopes)) {
+    return false
+  }
+
+  // Re-read tokens async to check if they're still expired
+  // Another process might have refreshed them
+  getClaudeAIOAuthTokens.cache?.clear?.()
+  clearKeychainCache()
+  const freshTokens = await getClaudeAIOAuthTokensAsync()
+  if (
+    !freshTokens?.refreshToken ||
+    !isOAuthTokenExpired(freshTokens.expiresAt)
+  ) {
+    return false
+  }
+
+  // Tokens are still expired, try to acquire lock and refresh
+  const claudeDir = getClaudeConfigHomeDir()
+  await mkdir(claudeDir, { recursive: true })
+
+  let release
+  try {
+    logEvent('tengu_oauth_token_refresh_lock_acquiring', {})
+    release = await lockfile.lock(claudeDir)
+    logEvent('tengu_oauth_token_refresh_lock_acquired', {})
+  } catch (err) {
+    if ((err as { code?: string }).code === 'ELOCKED') {
+      // Another process has the lock, let's retry if we haven't exceeded max retries
+      if (retryCount < MAX_RETRIES) {
+        logEvent('tengu_oauth_token_refresh_lock_retry', {
+          retryCount: retryCount + 1,
+        })
+        // Wait a bit before retrying
+        await sleep(1000 + Math.random() * 1000)
+        return checkAndRefreshOAuthTokenIfNeededImpl(retryCount + 1, force)
+      }
+      logEvent('tengu_oauth_token_refresh_lock_retry_limit_reached', {
+        maxRetries: MAX_RETRIES,
+      })
+      return false
+    }
+    logError(err)
+    logEvent('tengu_oauth_token_refresh_lock_error', {
+      error: errorMessage(
+        err,
+      ) as AnalyticsMetadata_I_VERIFIED_THIS_IS_NOT_CODE_OR_FILEPATHS,
+    })
+    return false
+  }
+  try {
+    // Check one more time after acquiring lock
+    getClaudeAIOAuthTokens.cache?.clear?.()
+    clearKeychainCache()
+    const lockedTokens = await getClaudeAIOAuthTokensAsync()
+    if (
+      !lockedTokens?.refreshToken ||
+      !isOAuthTokenExpired(lockedTokens.expiresAt)
+    ) {
+      logEvent('tengu_oauth_token_refresh_race_resolved', {})
+      return false
+    }
+
+    logEvent('tengu_oauth_token_refresh_starting', {})
+    const refreshedTokens = await refreshOAuthToken(lockedTokens.refreshToken, {
+      // For Claude.ai subscribers, omit scopes so the default
+      // CLAUDE_AI_OAUTH_SCOPES applies — this allows scope expansion
+      // (e.g. adding user:file_upload) on refresh without re-login.
+      scopes: shouldUseClaudeAIAuth(lockedTokens.scopes)
+        ? undefined
+        : lockedTokens.scopes,
+    })
+    saveOAuthTokensIfNeeded(refreshedTokens)
+
+    // Clear the cache after refreshing token
+    getClaudeAIOAuthTokens.cache?.clear?.()
+    clearKeychainCache()
+    return true
+  } catch (error) {
+    logError(error)
+
+    getClaudeAIOAuthTokens.cache?.clear?.()
+    clearKeychainCache()
+    const currentTokens = await getClaudeAIOAuthTokensAsync()
+    if (currentTokens && !isOAuthTokenExpired(currentTokens.expiresAt)) {
+      logEvent('tengu_oauth_token_refresh_race_recovered', {})
+      return true
+    }
+
+    return false
+  } finally {
+    logEvent('tengu_oauth_token_refresh_lock_releasing', {})
+    await release()
+    logEvent('tengu_oauth_token_refresh_lock_released', {})
+  }
+}
+
+export function isClaudeAISubscriber(): boolean {
+  if (!isAnthropicAuthEnabled()) {
+    return false
+  }
+
+  return shouldUseClaudeAIAuth(getClaudeAIOAuthTokens()?.scopes)
+}
+
+/**
+ * Check if the current OAuth token has the user:profile scope.
+ *
+ * Real /login tokens always include this scope. Env-var and file-descriptor
+ * tokens (service keys) hardcode scopes to ['user:inference'] only. Use this
+ * to gate calls to profile-scoped endpoints so service key sessions don't
+ * generate 403 storms against /api/oauth/profile, bootstrap, etc.
+ */
+export function hasProfileScope(): boolean {
+  return (
+    getClaudeAIOAuthTokens()?.scopes?.includes(CLAUDE_AI_PROFILE_SCOPE) ?? false
+  )
+}
+
+export function is1PApiCustomer(): boolean {
+  // 1P API customers are users who are NOT:
+  // 1. Claude.ai subscribers (Max, Pro, Enterprise, Team)
+  // 2. Vertex AI users
+  // 3. AWS Bedrock users
+  // 4. Foundry users
+
+  // Exclude Vertex, Bedrock, and Foundry customers
+  if (
+    isEnvTruthy(process.env.CLAUDE_CODE_USE_BEDROCK) ||
+    isEnvTruthy(process.env.CLAUDE_CODE_USE_VERTEX) ||
+    isEnvTruthy(process.env.CLAUDE_CODE_USE_FOUNDRY)
+  ) {
+    return false
+  }
+
+  // Exclude Claude.ai subscribers
+  if (isClaudeAISubscriber()) {
+    return false
+  }
+
+  // Everyone else is an API customer (OAuth API customers, direct API key users, etc.)
+  return true
+}
+
+/**
+ * Gets OAuth account information when Anthropic auth is enabled.
+ * Returns undefined when using external API keys or third-party services.
+ */
+export function getOauthAccountInfo(): AccountInfo | undefined {
+  return isAnthropicAuthEnabled() ? getGlobalConfig().oauthAccount : undefined
+}
+
+/**
+ * Checks if overage/extra usage provisioning is allowed for this organization.
+ * This mirrors the logic in apps/claude-ai `useIsOverageProvisioningAllowed` hook as closely as possible.
+ */
+export function isOverageProvisioningAllowed(): boolean {
+  const accountInfo = getOauthAccountInfo()
+  const billingType = accountInfo?.billingType
+
+  // Must be a Claude subscriber with a supported subscription type
+  if (!isClaudeAISubscriber() || !billingType) {
+    return false
+  }
+
+  // only allow Stripe and mobile billing types to purchase extra usage
+  if (
+    billingType !== 'stripe_subscription' &&
+    billingType !== 'stripe_subscription_contracted' &&
+    billingType !== 'apple_subscription' &&
+    billingType !== 'google_play_subscription'
+  ) {
+    return false
+  }
+
+  return true
+}
+
+// Returns whether the user has Opus access at all, regardless of whether they
+// are a subscriber or PayG.
+export function hasOpusAccess(): boolean {
+  const subscriptionType = getSubscriptionType()
+
+  return (
+    subscriptionType === 'max' ||
+    subscriptionType === 'enterprise' ||
+    subscriptionType === 'team' ||
+    subscriptionType === 'pro' ||
+    // subscriptionType === null covers both API users and the case where
+    // subscribers do not have subscription type populated. For those
+    // subscribers, when in doubt, we should not limit their access to Opus.
+    subscriptionType === null
+  )
+}
+
+export function getSubscriptionType(): SubscriptionType | null {
+  // Check for mock subscription type first (ANT-only testing)
+  if (shouldUseMockSubscription()) {
+    return getMockSubscriptionType()
+  }
+
+  if (!isAnthropicAuthEnabled()) {
+    return null
+  }
+  const oauthTokens = getClaudeAIOAuthTokens()
+  if (!oauthTokens) {
+    return null
+  }
+
+  return oauthTokens.subscriptionType ?? null
+}
+
+export function isMaxSubscriber(): boolean {
+  return getSubscriptionType() === 'max'
+}
+
+export function isTeamSubscriber(): boolean {
+  return getSubscriptionType() === 'team'
+}
+
+export function isTeamPremiumSubscriber(): boolean {
+  return (
+    getSubscriptionType() === 'team' &&
+    getRateLimitTier() === 'default_claude_max_5x'
+  )
+}
+
+export function isEnterpriseSubscriber(): boolean {
+  return getSubscriptionType() === 'enterprise'
+}
+
+export function isProSubscriber(): boolean {
+  return getSubscriptionType() === 'pro'
+}
+
+export function getRateLimitTier(): string | null {
+  if (!isAnthropicAuthEnabled()) {
+    return null
+  }
+  const oauthTokens = getClaudeAIOAuthTokens()
+  if (!oauthTokens) {
+    return null
+  }
+
+  return oauthTokens.rateLimitTier ?? null
+}
+
+export function getSubscriptionName(): string {
+  const subscriptionType = getSubscriptionType()
+
+  switch (subscriptionType) {
+    case 'enterprise':
+      return 'Claude Enterprise'
+    case 'team':
+      return 'Claude Team'
+    case 'max':
+      return 'Claude Max'
+    case 'pro':
+      return 'Claude Pro'
+    default:
+      return 'Claude API'
+  }
+}
+
+/** Check if using third-party services (Bedrock or Vertex or Foundry) */
+export function isUsing3PServices(): boolean {
+  return !!(
+    isEnvTruthy(process.env.CLAUDE_CODE_USE_BEDROCK) ||
+    isEnvTruthy(process.env.CLAUDE_CODE_USE_VERTEX) ||
+    isEnvTruthy(process.env.CLAUDE_CODE_USE_FOUNDRY)
+  )
+}
+
+/**
+ * Get the configured otelHeadersHelper from settings
+ */
+function getConfiguredOtelHeadersHelper(): string | undefined {
+  const mergedSettings = getSettings_DEPRECATED() || {}
+  return mergedSettings.otelHeadersHelper
+}
+
+/**
+ * Check if the configured otelHeadersHelper comes from project settings (projectSettings or localSettings)
+ */
+export function isOtelHeadersHelperFromProjectOrLocalSettings(): boolean {
+  const otelHeadersHelper = getConfiguredOtelHeadersHelper()
+  if (!otelHeadersHelper) {
+    return false
+  }
+
+  const projectSettings = getSettingsForSource('projectSettings')
+  const localSettings = getSettingsForSource('localSettings')
+  return (
+    projectSettings?.otelHeadersHelper === otelHeadersHelper ||
+    localSettings?.otelHeadersHelper === otelHeadersHelper
+  )
+}
+
+// Cache for debouncing otelHeadersHelper calls
+let cachedOtelHeaders: Record<string, string> | null = null
+let cachedOtelHeadersTimestamp = 0
+const DEFAULT_OTEL_HEADERS_DEBOUNCE_MS = 29 * 60 * 1000 // 29 minutes
+
+export function getOtelHeadersFromHelper(): Record<string, string> {
+  const otelHeadersHelper = getConfiguredOtelHeadersHelper()
+
+  if (!otelHeadersHelper) {
+    return {}
+  }
+
+  // Return cached headers if still valid (debounce)
+  const debounceMs = parseInt(
+    process.env.CLAUDE_CODE_OTEL_HEADERS_HELPER_DEBOUNCE_MS ||
+      DEFAULT_OTEL_HEADERS_DEBOUNCE_MS.toString(),
+  )
+  if (
+    cachedOtelHeaders &&
+    Date.now() - cachedOtelHeadersTimestamp < debounceMs
+  ) {
+    return cachedOtelHeaders
+  }
+
+  if (isOtelHeadersHelperFromProjectOrLocalSettings()) {
+    // Check if trust has been established for this project
+    const hasTrust = checkHasTrustDialogAccepted()
+    if (!hasTrust) {
+      return {}
+    }
+  }
+
+  try {
+    const result = execSyncWithDefaults_DEPRECATED(otelHeadersHelper, {
+      timeout: 30000, // 30 seconds - allows for auth service latency
+    })
+      ?.toString()
+      .trim()
+    if (!result) {
+      throw new Error('otelHeadersHelper did not return a valid value')
+    }
+
+    const headers = jsonParse(result)
+    if (
+      typeof headers !== 'object' ||
+      headers === null ||
+      Array.isArray(headers)
+    ) {
+      throw new Error(
+        'otelHeadersHelper must return a JSON object with string key-value pairs',
+      )
+    }
+
+    // Validate all values are strings
+    for (const [key, value] of Object.entries(headers)) {
+      if (typeof value !== 'string') {
+        throw new Error(
+          `otelHeadersHelper returned non-string value for key "${key}": ${typeof value}`,
+        )
+      }
+    }
+
+    // Cache the result
+    cachedOtelHeaders = headers as Record<string, string>
+    cachedOtelHeadersTimestamp = Date.now()
+
+    return cachedOtelHeaders
+  } catch (error) {
+    logError(
+      new Error(
+        `Error getting OpenTelemetry headers from otelHeadersHelper (in settings): ${errorMessage(error)}`,
+      ),
+    )
+    throw error
+  }
+}
+
+function isConsumerPlan(plan: SubscriptionType): plan is 'max' | 'pro' {
+  return plan === 'max' || plan === 'pro'
+}
+
+export function isConsumerSubscriber(): boolean {
+  const subscriptionType = getSubscriptionType()
+  return (
+    isClaudeAISubscriber() &&
+    subscriptionType !== null &&
+    isConsumerPlan(subscriptionType)
+  )
+}
+
+export type UserAccountInfo = {
+  subscription?: string
+  tokenSource?: string
+  apiKeySource?: ApiKeySource
+  organization?: string
+  email?: string
+}
+
+export function getAccountInformation() {
+  const apiProvider = getAPIProvider()
+  // Only provide account info for first-party Anthropic API
+  if (apiProvider !== 'firstParty') {
+    return undefined
+  }
+  const { source: authTokenSource } = getAuthTokenSource()
+  const accountInfo: UserAccountInfo = {}
+  if (
+    authTokenSource === 'CLAUDE_CODE_OAUTH_TOKEN' ||
+    authTokenSource === 'CLAUDE_CODE_OAUTH_TOKEN_FILE_DESCRIPTOR'
+  ) {
+    accountInfo.tokenSource = authTokenSource
+  } else if (isClaudeAISubscriber()) {
+    accountInfo.subscription = getSubscriptionName()
+  } else {
+    accountInfo.tokenSource = authTokenSource
+  }
+  const { key: apiKey, source: apiKeySource } = getAnthropicApiKeyWithSource()
+  if (apiKey) {
+    accountInfo.apiKeySource = apiKeySource
+  }
+
+  // We don't know the organization if we're relying on an external API key or auth token
+  if (
+    authTokenSource === 'claude.ai' ||
+    apiKeySource === '/login managed key'
+  ) {
+    // Get organization name from OAuth account info
+    const orgName = getOauthAccountInfo()?.organizationName
+    if (orgName) {
+      accountInfo.organization = orgName
+    }
+  }
+  const email = getOauthAccountInfo()?.emailAddress
+  if (
+    (authTokenSource === 'claude.ai' ||
+      apiKeySource === '/login managed key') &&
+    email
+  ) {
+    accountInfo.email = email
+  }
+  return accountInfo
+}
+
+/**
+ * Result of org validation — either success or a descriptive error.
+ */
+export type OrgValidationResult =
+  | { valid: true }
+  | { valid: false; message: string }
+
+/**
+ * Validate that the active OAuth token belongs to the organization required
+ * by `forceLoginOrgUUID` in managed settings. Returns a result object
+ * rather than throwing so callers can choose how to surface the error.
+ *
+ * Fails closed: if `forceLoginOrgUUID` is set and we cannot determine the
+ * token's org (network error, missing profile data), validation fails.
+ */
+export async function validateForceLoginOrg(): Promise<OrgValidationResult> {
+  // `claude ssh` remote: real auth lives on the local machine and is injected
+  // by the proxy. The placeholder token can't be validated against the profile
+  // endpoint. The local side already ran this check before establishing the session.
+  if (process.env.ANTHROPIC_UNIX_SOCKET) {
+    return { valid: true }
+  }
+
+  if (!isAnthropicAuthEnabled()) {
+    return { valid: true }
+  }
+
+  const requiredOrgUuid =
+    getSettingsForSource('policySettings')?.forceLoginOrgUUID
+  if (!requiredOrgUuid) {
+    return { valid: true }
+  }
+
+  // Ensure the access token is fresh before hitting the profile endpoint.
+  // No-op for env-var tokens (refreshToken is null).
+  await checkAndRefreshOAuthTokenIfNeeded()
+
+  const tokens = getClaudeAIOAuthTokens()
+  if (!tokens) {
+    return { valid: true }
+  }
+
+  // Always fetch the authoritative org UUID from the profile endpoint.
+  // Even keychain-sourced tokens verify server-side: the cached org UUID
+  // in ~/.claude.json is user-writable and cannot be trusted.
+  const { source } = getAuthTokenSource()
+  const isEnvVarToken =
+    source === 'CLAUDE_CODE_OAUTH_TOKEN' ||
+    source === 'CLAUDE_CODE_OAUTH_TOKEN_FILE_DESCRIPTOR'
+
+  const profile = await getOauthProfileFromOauthToken(tokens.accessToken)
+  if (!profile) {
+    // Fail closed — we can't verify the org
+    return {
+      valid: false,
+      message:
+        `Unable to verify organization for the current authentication token.\n` +
+        `This machine requires organization ${requiredOrgUuid} but the profile could not be fetched.\n` +
+        `This may be a network error, or the token may lack the user:profile scope required for\n` +
+        `verification (tokens from 'claude setup-token' do not include this scope).\n` +
+        `Try again, or obtain a full-scope token via 'claude auth login'.`,
+    }
+  }
+
+  const tokenOrgUuid = profile.organization.uuid
+  if (tokenOrgUuid === requiredOrgUuid) {
+    return { valid: true }
+  }
+
+  if (isEnvVarToken) {
+    const envVarName =
+      source === 'CLAUDE_CODE_OAUTH_TOKEN'
+        ? 'CLAUDE_CODE_OAUTH_TOKEN'
+        : 'CLAUDE_CODE_OAUTH_TOKEN_FILE_DESCRIPTOR'
+    return {
+      valid: false,
+      message:
+        `The ${envVarName} environment variable provides a token for a\n` +
+        `different organization than required by this machine's managed settings.\n\n` +
+        `Required organization: ${requiredOrgUuid}\n` +
+        `Token organization:   ${tokenOrgUuid}\n\n` +
+        `Remove the environment variable or obtain a token for the correct organization.`,
+    }
+  }
+
+  return {
+    valid: false,
+    message:
+      `Your authentication token belongs to organization ${tokenOrgUuid},\n` +
+      `but this machine requires organization ${requiredOrgUuid}.\n\n` +
+      `Please log in with the correct organization: claude auth login`,
+  }
+}
+
+class GcpCredentialsTimeoutError extends Error {}