feat(telemetry): measure macOS stale-daemon adoption and cwd denials (#18043)

* feat(telemetry): measure macOS stale-daemon adoption and cwd denials

Adds two enum-only PostHog events so #17696 can be sized instead of guessed at:

- daemon_adopted: once per macOS launch that keeps a daemon an earlier app
  launch forked (invisible to daemon_lifecycle, which only sees replacements).
  Carries app-version match, spawner-path class (installed app / Squirrel
  ShipIt cache / other / missing), the existing TCC attribution verdict, and
  the bucketed live-session count.
- daemon_pty_cwd_denied: the symptom itself. The daemon probes the requested
  cwd in its own process (only its TCC context counts) and returns an additive
  cwdReadableByDaemon field; the app emits only when the daemon was denied AND
  the app can read the same path, so a missing or genuinely unreadable cwd
  never counts. Non-permission errors read as readable on purpose.

Both emitters swallow every failure; nothing here can delay or fail daemon
startup or a PTY spawn. Off macOS neither event fires. The new wire field is
optional, so older daemons and clients are unaffected.

* fix(telemetry): keep cwd-denial classification inside the swallow guard

Read the pid record at emit time (inside the try) rather than passing the
adapter's startup snapshot: a throwing app-environment read can no longer
escape spawn(), and a denial after a respawn is billed to the daemon that
actually spawned the PTY.

src/main/daemon/daemon-adoption-telemetry-event.test.ts

@@ -0,0 +1,168 @@
+import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest'
+import type { ParsedDaemonPid } from './daemon-pid-file-parse'
+import { validate } from '../telemetry/validator'
+
+const { trackMock, accessSyncMock, existsSyncMock, readFileSyncMock, getVersionMock } = vi.hoisted(
+  () => ({
+    trackMock: vi.fn(),
+    accessSyncMock: vi.fn(),
+    existsSyncMock: vi.fn(() => true),
+    readFileSyncMock: vi.fn(),
+    getVersionMock: vi.fn(() => '1.4.191')
+  })
+)
+vi.mock('../telemetry/client', () => ({ track: trackMock }))
+vi.mock('node:fs', async (importOriginal) => ({
+  ...(await importOriginal<Record<string, unknown>>()),
+  accessSync: accessSyncMock,
+  existsSync: existsSyncMock,
+  readFileSync: readFileSyncMock
+}))
+vi.mock('node:os', async (importOriginal) => ({
+  ...(await importOriginal<Record<string, unknown>>()),
+  homedir: () => '/Users/alice'
+}))
+vi.mock('../../shared/app-environment', () => ({
+  getAppEnvironment: () => ({ getVersion: getVersionMock })
+}))
+
+import {
+  classifyDaemonAdoptionOrigin,
+  trackDaemonAdopted,
+  trackDaemonPtyCwdDeniedIfDiverged
+} from './daemon-adoption-telemetry-event'
+
+const stalePidRecord: ParsedDaemonPid = {
+  pid: 1530,
+  startedAtMs: 1,
+  entryPath: '/x/daemon-entry.js',
+  appVersion: '1.4.187',
+  launchNonce: 'n',
+  linuxStartTicks: null,
+  bootId: null,
+  spawnerExecPath:
+    '/Users/alice/Library/Caches/com.stablyai.orca.ShipIt/u/Orca.app/Contents/MacOS/Orca'
+}
+const origin = { app_version_match: 'different', spawner_path_class: 'updater-cache' } as const
+const PID_PATH = '/fake/daemon.pid'
+
+beforeEach(() => {
+  trackMock.mockReset()
+  accessSyncMock.mockReset()
+  existsSyncMock.mockReset().mockReturnValue(true)
+  readFileSyncMock.mockReset().mockReturnValue(JSON.stringify(stalePidRecord))
+  vi.spyOn(process, 'platform', 'get').mockReturnValue('darwin')
+})
+
+afterEach(() => {
+  vi.restoreAllMocks()
+})
+
+describe('classifyDaemonAdoptionOrigin', () => {
+  it('compares the recorded app version and classifies the spawner path', () => {
+    expect(classifyDaemonAdoptionOrigin(stalePidRecord)).toEqual(origin)
+    expect(classifyDaemonAdoptionOrigin({ ...stalePidRecord, appVersion: '1.4.191' })).toEqual({
+      app_version_match: 'same',
+      spawner_path_class: 'updater-cache'
+    })
+    expect(classifyDaemonAdoptionOrigin(null)).toEqual({
+      app_version_match: 'unknown',
+      spawner_path_class: 'unknown'
+    })
+  })
+})
+
+describe('trackDaemonAdopted', () => {
+  it('emits a validator-accepted payload', () => {
+    trackDaemonAdopted(stalePidRecord, 'intact', 7)
+    expect(trackMock).toHaveBeenCalledTimes(1)
+    const [name, props] = trackMock.mock.calls[0]
+    expect(name).toBe('daemon_adopted')
+    expect(props).toEqual({
+      ...origin,
+      tcc_attribution: 'intact',
+      live_session_count_bucket: '6+'
+    })
+    expect(validate('daemon_adopted', props).ok).toBe(true)
+  })
+
+  it('swallows a throwing telemetry client', () => {
+    trackMock.mockImplementationOnce(() => {
+      throw new Error('posthog exploded')
+    })
+    expect(() => trackDaemonAdopted(null, 'unknown', null)).not.toThrow()
+  })
+})
+
+describe('trackDaemonPtyCwdDeniedIfDiverged', () => {
+  it('emits only when the daemon was denied and the app can read the same cwd', () => {
+    trackDaemonPtyCwdDeniedIfDiverged('/Users/alice/Documents/repo', false, PID_PATH)
+    expect(accessSyncMock).toHaveBeenCalledWith('/Users/alice/Documents/repo', expect.any(Number))
+    expect(trackMock).toHaveBeenCalledTimes(1)
+    const [name, props] = trackMock.mock.calls[0]
+    expect(name).toBe('daemon_pty_cwd_denied')
+    expect(props).toEqual({ cwd_class: 'documents', ...origin })
+    expect(validate('daemon_pty_cwd_denied', props).ok).toBe(true)
+  })
+
+  // False positives would drown the signal this event exists to measure, so every
+  // non-divergent shape must stay silent.
+  it('stays silent when the daemon could read the cwd or did not report', () => {
+    trackDaemonPtyCwdDeniedIfDiverged('/Users/alice/Documents/repo', true, PID_PATH)
+    trackDaemonPtyCwdDeniedIfDiverged('/Users/alice/Documents/repo', undefined, PID_PATH)
+    trackDaemonPtyCwdDeniedIfDiverged(undefined, false, PID_PATH)
+    expect(accessSyncMock).not.toHaveBeenCalled()
+    expect(trackMock).not.toHaveBeenCalled()
+  })
+
+  it('stays silent when the app cannot read the cwd either (no divergence)', () => {
+    accessSyncMock.mockImplementation(() => {
+      throw Object.assign(new Error('EACCES'), { code: 'EACCES' })
+    })
+    trackDaemonPtyCwdDeniedIfDiverged('/Users/alice/Documents/repo', false, PID_PATH)
+    expect(trackMock).not.toHaveBeenCalled()
+  })
+
+  it('attributes the denial to the daemon recorded right now, not a startup snapshot', () => {
+    readFileSyncMock.mockReturnValue(
+      JSON.stringify({
+        ...stalePidRecord,
+        appVersion: '1.4.191',
+        spawnerExecPath: '/Applications/Orca.app/Contents/MacOS/Orca'
+      })
+    )
+    trackDaemonPtyCwdDeniedIfDiverged('/Users/alice/Documents/repo', false, PID_PATH)
+    expect(readFileSyncMock).toHaveBeenCalledWith(PID_PATH, 'utf8')
+    expect(trackMock.mock.calls[0][1]).toEqual({
+      cwd_class: 'documents',
+      app_version_match: 'same',
+      spawner_path_class: 'applications'
+    })
+  })
+
+  it('swallows a throwing app environment or pid-record read instead of failing the spawn', () => {
+    getVersionMock.mockImplementationOnce(() => {
+      throw new Error('AppEnvironment not initialized')
+    })
+    expect(() =>
+      trackDaemonPtyCwdDeniedIfDiverged('/Users/alice/Documents/repo', false, PID_PATH)
+    ).not.toThrow()
+    expect(trackMock).not.toHaveBeenCalled()
+  })
+
+  it('stays silent off macOS', () => {
+    vi.spyOn(process, 'platform', 'get').mockReturnValue('linux')
+    trackDaemonPtyCwdDeniedIfDiverged('/home/alice/Documents/repo', false, PID_PATH)
+    expect(accessSyncMock).not.toHaveBeenCalled()
+    expect(trackMock).not.toHaveBeenCalled()
+  })
+
+  it('swallows a throwing telemetry client', () => {
+    trackMock.mockImplementationOnce(() => {
+      throw new Error('posthog exploded')
+    })
+    expect(() =>
+      trackDaemonPtyCwdDeniedIfDiverged('/Users/alice/Documents/repo', false, PID_PATH)
+    ).not.toThrow()
+  })
+})

src/main/daemon/daemon-adoption-telemetry-event.ts

@@ -0,0 +1,81 @@
+// App-side emitters for `daemon_adopted` and `daemon_pty_cwd_denied` (#17696). Both sit on the
+// daemon launch / PTY spawn path, so every failure dies here — telemetry can never cost a terminal.
+
+import { accessSync, constants as fsConstants, existsSync } from 'node:fs'
+import { homedir } from 'node:os'
+import { getAppEnvironment } from '../../shared/app-environment'
+import {
+  classifyDaemonPtyCwd,
+  classifyDaemonSpawnerPath,
+  type DaemonAdoptedAppVersionMatch,
+  type DaemonSpawnerPathClass
+} from '../../shared/daemon-adoption-telemetry'
+import { bucketDaemonLiveSessionCount } from '../../shared/daemon-lifecycle-telemetry'
+import type { EventProps } from '../../shared/telemetry-events'
+import { track } from '../telemetry/client'
+import { readDaemonPidRecord } from './daemon-endpoint-incarnation'
+import type { ParsedDaemonPid } from './daemon-pid-file-parse'
+import type { MacDaemonTccAttributionHealth } from './daemon-tcc-attribution'
+
+export type DaemonAdoptionOrigin = Pick<
+  EventProps<'daemon_pty_cwd_denied'>,
+  'app_version_match' | 'spawner_path_class'
+>
+
+/** Classifies the adopted daemon's pid record against the running app; enum-only by construction. */
+export function classifyDaemonAdoptionOrigin(
+  pidRecord: ParsedDaemonPid | null
+): DaemonAdoptionOrigin {
+  const appVersionMatch: DaemonAdoptedAppVersionMatch = !pidRecord?.appVersion
+    ? 'unknown'
+    : pidRecord.appVersion === getAppEnvironment().getVersion()
+      ? 'same'
+      : 'different'
+  const spawnerPathClass: DaemonSpawnerPathClass = classifyDaemonSpawnerPath(
+    pidRecord?.spawnerExecPath ?? null,
+    existsSync
+  )
+  return { app_version_match: appVersionMatch, spawner_path_class: spawnerPathClass }
+}
+
+// Adopted a daemon that a previous app launch forked (macOS only; that is where attribution matters).
+export function trackDaemonAdopted(
+  pidRecord: ParsedDaemonPid | null,
+  tccAttribution: MacDaemonTccAttributionHealth,
+  liveSessionCount: number | null
+): void {
+  try {
+    track('daemon_adopted', {
+      ...classifyDaemonAdoptionOrigin(pidRecord),
+      tcc_attribution: tccAttribution,
+      live_session_count_bucket: bucketDaemonLiveSessionCount(liveSessionCount)
+    })
+  } catch {
+    // Telemetry is best-effort; a dropped event must not fail daemon adoption.
+  }
+}
+
+/**
+ * Emits only on proven divergence: the daemon reported the cwd unreadable AND this process can
+ * read it. A cwd neither can read (chmod, ENOENT, unmounted volume) is not the #17696 shape.
+ */
+export function trackDaemonPtyCwdDeniedIfDiverged(
+  cwd: string | undefined,
+  cwdReadableByDaemon: boolean | undefined,
+  pidPath: string | null
+): void {
+  try {
+    if (process.platform !== 'darwin' || !cwd || cwdReadableByDaemon !== false) {
+      return
+    }
+    accessSync(cwd, fsConstants.R_OK | fsConstants.X_OK)
+    // Why read now, not the adapter's startup snapshot: a respawn swaps the daemon under a
+    // long-lived adapter, and the denial must be attributed to the daemon that just spawned.
+    track('daemon_pty_cwd_denied', {
+      cwd_class: classifyDaemonPtyCwd(cwd, homedir()),
+      ...classifyDaemonAdoptionOrigin(readDaemonPidRecord(pidPath))
+    })
+  } catch {
+    // Either the app cannot read it (no divergence) or telemetry failed; neither may reach the caller.
+  }
+}

src/main/daemon/daemon-create-or-attach-result.ts

@@ -14,6 +14,12 @@ export type DaemonCreateOrAttachResult = {
   wslDistro?: string | null
   agentSessionEnsure?: AgentSessionClaimedSpawnResult
   incarnationId?: PtyIncarnationId
+  /**
+   * Whether the daemon process itself could read the requested cwd at spawn. Only the daemon's own
+   * verdict counts: macOS TCC scopes folder access per process tree, so the app's view of the same
+   * path proves nothing about the daemon's (#17696). Omitted by daemons predating this field.
+   */
+  cwdReadableByDaemon?: boolean
 }
 
 export function getDaemonSessionResultMetadata(session: {

src/main/daemon/daemon-init-dependency-mocks.ts

@@ -50,7 +50,8 @@ export function createDaemonInitModuleFactories(state: DaemonInitMockState) {
     unbindLocalProviderListenersMock,
     rebindLocalProviderListenersMock,
     trackDaemonReplacedMock,
-    trackDaemonRetiredMock
+    trackDaemonRetiredMock,
+    trackDaemonAdoptedMock
   } = state
 
   // Why: both fakes are annotated with constructor types so the exported factories widen to
@@ -82,6 +83,9 @@ export function createDaemonInitModuleFactories(state: DaemonInitMockState) {
           if (result.mode) {
             this.handle.mode = result.mode
           }
+          if (result.adopted) {
+            this.handle.adopted = true
+          }
           return {
             socketPath: result.socketPath,
             tokenPath: result.tokenPath
@@ -199,6 +203,9 @@ export function createDaemonInitModuleFactories(state: DaemonInitMockState) {
       trackDaemonReplaced: trackDaemonReplacedMock,
       trackDaemonRetired: trackDaemonRetiredMock
     }),
+    daemonAdoptionTelemetryEvent: () => ({
+      trackDaemonAdopted: trackDaemonAdoptedMock
+    }),
     daemonSpawner: () => ({
       DaemonSpawner: MockDaemonSpawner,
       getDaemonSocketPath: (_dir: string, version?: number) =>

src/main/daemon/daemon-init-fresh-import.ts

@@ -41,7 +41,8 @@ export async function importFreshDaemonInit(state: DaemonInitMockState) {
     unbindLocalProviderListenersMock,
     rebindLocalProviderListenersMock,
     trackDaemonReplacedMock,
-    trackDaemonRetiredMock
+    trackDaemonRetiredMock,
+    trackDaemonAdoptedMock
   } = state
 
   vi.resetModules()
@@ -64,6 +65,7 @@ export async function importFreshDaemonInit(state: DaemonInitMockState) {
   rebindLocalProviderListenersMock.mockClear()
   trackDaemonReplacedMock.mockClear()
   trackDaemonRetiredMock.mockClear()
+  trackDaemonAdoptedMock.mockClear()
   checkDaemonHealthMock.mockClear()
   checkDaemonHealthMock.mockResolvedValue('healthy')
   healthCheckDaemonMock.mockClear()

src/main/daemon/daemon-init-mock-types.ts

@@ -47,6 +47,7 @@ export type MockAdapterConstructor = new (opts: MockAdapter['options']) => MockA
 /** Handle the fake spawner hands back from ensureRunning/getHandle. */
 export type MockSpawnerHandle = {
   mode?: 'degraded-new-pty-fallback'
+  adopted?: true
   releaseAdoptionLease?: () => void
   shutdown: () => Promise<void>
 }
@@ -95,6 +96,7 @@ export type EnsureRunningOverride = () => Promise<{
   socketPath: string
   tokenPath: string
   mode?: 'degraded-new-pty-fallback'
+  adopted?: true
 }>
 
 /** Every stub daemon-init's suites share, plus the control knobs they mutate per test. */
@@ -143,6 +145,7 @@ export type DaemonInitMockState = {
   rebindLocalProviderListenersMock: Mock<(...args: unknown[]) => void>
   trackDaemonReplacedMock: Mock<(...args: unknown[]) => void>
   trackDaemonRetiredMock: Mock<(...args: unknown[]) => void>
+  trackDaemonAdoptedMock: Mock<(...args: unknown[]) => void>
 }
 
 /** net.connect stubs the suites install in beforeEach. */

src/main/daemon/daemon-init-provider-installation.test.ts

@@ -2,6 +2,8 @@ import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest'
 
 const {
   isPackagedMock,
+  getMacDaemonTccAttributionHealthMock,
+  trackDaemonAdoptedMock,
   probeSocketExistsMock,
   readFileSyncMock,
   unlinkSyncMock,
@@ -42,6 +44,7 @@ vi.mock('./daemon-process-start-time', () => moduleFactories.daemonProcessStartT
 vi.mock('./daemon-pid-file-parse', () => moduleFactories.daemonPidFileParse())
 vi.mock('./client', () => moduleFactories.client())
 vi.mock('./daemon-lifecycle-event', () => moduleFactories.daemonLifecycleEvent())
+vi.mock('./daemon-adoption-telemetry-event', () => moduleFactories.daemonAdoptionTelemetryEvent())
 vi.mock('./daemon-spawner', () => moduleFactories.daemonSpawner())
 vi.mock('./daemon-pty-adapter', () => moduleFactories.daemonPtyAdapter())
 vi.mock('../ipc/pty', () => moduleFactories.ipcPty())
@@ -228,6 +231,48 @@ describe('daemon-init: runRestartDaemon (7-step sequence)', () => {
     expect(adapterInstances[1].disconnectOnly).toHaveBeenCalledOnce()
   })
 
+  // #17696: adopting a daemon from an earlier app launch is invisible to daemon_lifecycle, so
+  // it gets its own event — macOS only, and only for adopted (not freshly forked) daemons.
+  it('reports a macOS daemon adoption with its TCC attribution and live session bucket', async () => {
+    vi.spyOn(process, 'platform', 'get').mockReturnValue('darwin')
+    const mod = await importFresh()
+    ensureRunningOverrides.push(async () => ({
+      socketPath: '/fake/adopted-socket',
+      tokenPath: '/fake/adopted-token',
+      adopted: true
+    }))
+    getMacDaemonTccAttributionHealthMock.mockResolvedValueOnce('severed')
+    defaultListSessionsSessions.push({ sessionId: 'wt-1@@a' }, { sessionId: 'wt-1@@b' })
+
+    await mod.initDaemonPtyProvider()
+    await vi.waitFor(() => expect(trackDaemonAdoptedMock).toHaveBeenCalledOnce())
+
+    // null pid record: the harness has no pid file, which the emitter classifies as 'unknown'.
+    expect(trackDaemonAdoptedMock).toHaveBeenCalledWith(null, 'severed', 2)
+    vi.restoreAllMocks()
+  })
+
+  it('does not report adoption for a freshly forked daemon or off macOS', async () => {
+    vi.spyOn(process, 'platform', 'get').mockReturnValue('darwin')
+    const mod = await importFresh()
+    await mod.initDaemonPtyProvider()
+    await new Promise((resolve) => setImmediate(resolve))
+    expect(trackDaemonAdoptedMock).not.toHaveBeenCalled()
+    vi.restoreAllMocks()
+
+    vi.spyOn(process, 'platform', 'get').mockReturnValue('linux')
+    const linuxMod = await importFresh()
+    ensureRunningOverrides.push(async () => ({
+      socketPath: '/fake/adopted-socket',
+      tokenPath: '/fake/adopted-token',
+      adopted: true
+    }))
+    await linuxMod.initDaemonPtyProvider()
+    await new Promise((resolve) => setImmediate(resolve))
+    expect(trackDaemonAdoptedMock).not.toHaveBeenCalled()
+    vi.restoreAllMocks()
+  })
+
   it('routes fresh PTYs to the local fallback when a preserved daemon cannot spawn new PTYs', async () => {
     const mod = await importFresh()
     ensureRunningOverrides.push(async () => ({

src/main/daemon/daemon-init-test-harness.ts

@@ -156,6 +156,7 @@ function createDaemonInitMockState(): DaemonInitMockState {
   const rebindLocalProviderListenersMock = vi.fn()
   const trackDaemonReplacedMock = vi.fn()
   const trackDaemonRetiredMock = vi.fn()
+  const trackDaemonAdoptedMock = vi.fn()
 
   return {
     getPathMock,
@@ -197,7 +198,8 @@ function createDaemonInitMockState(): DaemonInitMockState {
     unbindLocalProviderListenersMock,
     rebindLocalProviderListenersMock,
     trackDaemonReplacedMock,
-    trackDaemonRetiredMock
+    trackDaemonRetiredMock,
+    trackDaemonAdoptedMock
   }
 }
 

src/main/daemon/daemon-out-of-process-launcher.ts

@@ -41,6 +41,7 @@ function createPreservedDaemonHandle(
   mode?: 'degraded-new-pty-fallback'
 ): DaemonProcessHandle {
   const handle: DaemonProcessHandle = {
+    adopted: true,
     shutdown: async () => {
       await cleanupDaemonForProtocol(runtimeDir, protocolVersion)
     }

src/main/daemon/daemon-provider-init.ts

@@ -24,7 +24,10 @@ import {
 import type { DaemonProvider } from './daemon-provider-routing'
 import { installDaemonProvider } from './daemon-provider-state'
 import { DegradedDaemonPtyProvider } from './degraded-daemon-pty-provider'
+import { trackDaemonAdopted } from './daemon-adoption-telemetry-event'
+import { readDaemonPidRecord } from './daemon-endpoint-incarnation'
 import { trackDaemonRetired } from './daemon-lifecycle-event'
+import { getMacDaemonTccAttributionHealth } from './daemon-tcc-attribution'
 import { DaemonPtyAdapter } from './daemon-pty-adapter'
 import type { DaemonRespawnReason } from './daemon-pty-runtime-state'
 import { DaemonPtyRouter } from './daemon-pty-router'
@@ -156,9 +159,37 @@ export async function initDaemonPtyProvider(
   logDaemonMilestone('daemon-init-done', {
     legacyAdapters: legacyAdapters.length
   })
+  if (process.platform === 'darwin' && newSpawner.getHandle()?.adopted) {
+    void reportDaemonAdoption(runtimeDir, info.socketPath, info.tokenPath, newAdapter)
+  }
   await reconcileSeededClaudeLivePtys(routedAdapter)
 }
 
+// Why off the init path: this is measurement of an adopted daemon (#17696), and neither its probes nor their failure may delay or fail startup.
+async function reportDaemonAdoption(
+  runtimeDir: string,
+  socketPath: string,
+  tokenPath: string,
+  adapter: DaemonPtyAdapter
+): Promise<void> {
+  try {
+    const [tccAttribution, liveSessionCount] = await Promise.all([
+      getMacDaemonTccAttributionHealth(runtimeDir, socketPath, tokenPath),
+      adapter.listSessions().then(
+        (sessions) => sessions.length,
+        () => null
+      )
+    ])
+    trackDaemonAdopted(
+      readDaemonPidRecord(getDaemonPidPath(runtimeDir)),
+      tccAttribution,
+      liveSessionCount
+    )
+  } catch {
+    // Best-effort measurement only.
+  }
+}
+
 // Why: release gate ids only for daemon-confirmed-dead sessions; keep seeds on listing failure since releasing early can rotate a live CLI's refresh token.
 async function reconcileSeededClaudeLivePtys(provider: DaemonProvider): Promise<void> {
   if (!hasSeededUnconfirmedClaudePtys()) {

src/main/daemon/daemon-pty-session-spawn.ts

@@ -4,6 +4,7 @@ import type {
   HistoryRecoveryContext,
   PendingDaemonSpawnOperation
 } from './daemon-pty-runtime-state'
+import { trackDaemonPtyCwdDeniedIfDiverged } from './daemon-adoption-telemetry-event'
 import { STABLE_PANE_ATTACH_ONLY_DAEMON_PROTOCOL_VERSION } from './daemon-protocol-version'
 import { TerminalKilledError } from './daemon-pty-lifecycle-errors'
 import { DaemonPtySpawnResult } from './daemon-pty-spawn-result'
@@ -246,6 +247,9 @@ export abstract class DaemonPtySessionSpawn extends DaemonPtySpawnResult {
     }
     activeSpawnContext = context
     const result = await this.createOrAttachSpawn(context, context.historySeedSegments)
+    if (result.isNew && !attachOnly) {
+      trackDaemonPtyCwdDeniedIfDiverged(effectiveCwd, result.cwdReadableByDaemon, this.pidPath)
+    }
     return this.finishSpawn(context, result)
   }
 

src/main/daemon/daemon-spawner.ts

@@ -31,6 +31,8 @@ export type DaemonPidFile = {
 
 export type DaemonProcessHandle = {
   mode?: 'degraded-new-pty-fallback'
+  /** Set when the launcher kept a daemon some earlier app launch forked, rather than forking one. */
+  adopted?: true
   releaseAdoptionLease?(): void
   shutdown(): Promise<void>
 }

src/main/daemon/daemon-terminal-admission.ts

@@ -161,7 +161,10 @@ export class DaemonTerminalAdmission {
       ...(result.launchAgent ? { launchAgent: result.launchAgent } : {}),
       wslDistro: result.wslDistro,
       ...(result.historySeeded !== undefined ? { historySeeded: result.historySeeded } : {}),
-      ...(result.agentSessionEnsure ? { agentSessionEnsure: result.agentSessionEnsure } : {})
+      ...(result.agentSessionEnsure ? { agentSessionEnsure: result.agentSessionEnsure } : {}),
+      ...(result.cwdReadableByDaemon !== undefined
+        ? { cwdReadableByDaemon: result.cwdReadableByDaemon }
+        : {})
     }
   }
 

src/main/daemon/terminal-host-create-contract.ts

@@ -54,4 +54,6 @@ export type CreateOrAttachResult = {
   attachToken: symbol
   incarnationId: PtyIncarnationId
   agentSessionEnsure?: AgentSessionClaimedSpawnResult
+  /** Daemon-process verdict on the spawn cwd; only set on a fresh spawn that was given a cwd. */
+  cwdReadableByDaemon?: boolean
 }

src/main/daemon/terminal-host-cwd-readability.test.ts

@@ -0,0 +1,75 @@
+import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest'
+import type { SubprocessHandle } from './session-subprocess-handle'
+import { TerminalHost, type TerminalHostOptions } from './terminal-host'
+
+vi.mock('../pty-descendant-termination', () => ({ killWithDescendantSweep: vi.fn() }))
+
+function createMockSubprocess(): SubprocessHandle {
+  let onExitCb: ((code: number) => void) | null = null
+  return {
+    pid: 99999,
+    getForegroundProcess: vi.fn(() => null),
+    write: vi.fn(),
+    resize: vi.fn(),
+    kill: vi.fn(() => {
+      setTimeout(() => onExitCb?.(0), 5)
+    }),
+    terminateOwnedTree: () => 'unavailable' as const,
+    forceKill: vi.fn(() => onExitCb?.(137)),
+    signal: vi.fn(),
+    onData() {},
+    onExit(cb) {
+      onExitCb = cb
+    },
+    dispose: vi.fn()
+  }
+}
+
+// #17696: only the daemon process can say whether TCC lets it read the cwd, so its verdict
+// rides on the create result. A non-permission failure must never read as denial.
+describe('TerminalHost cwd readability verdict', () => {
+  let host: TerminalHost
+  let platformDescriptor: PropertyDescriptor | undefined
+
+  beforeEach(() => {
+    platformDescriptor = Object.getOwnPropertyDescriptor(process, 'platform')
+    Object.defineProperty(process, 'platform', { configurable: true, value: 'linux' })
+    const spawnSubprocess: TerminalHostOptions['spawnSubprocess'] = () => createMockSubprocess()
+    host = new TerminalHost({ spawnSubprocess })
+  })
+
+  afterEach(async () => {
+    await host.dispose()
+    if (platformDescriptor) {
+      Object.defineProperty(process, 'platform', platformDescriptor)
+    }
+  })
+
+  const create = (sessionId: string, cwd?: string) =>
+    host.createOrAttach({
+      sessionId,
+      cols: 80,
+      rows: 24,
+      ...(cwd ? { cwd } : {}),
+      streamClient: { onData: vi.fn(), onExit: vi.fn() }
+    })
+
+  it('reports a readable cwd as readable', async () => {
+    expect((await create('readable', process.cwd())).cwdReadableByDaemon).toBe(true)
+  })
+
+  it('reports a missing cwd as readable — absence is not a permission denial', async () => {
+    expect((await create('missing', '/definitely/not/a/real/dir')).cwdReadableByDaemon).toBe(true)
+  })
+
+  it('omits the verdict when no cwd was requested', async () => {
+    expect((await create('no-cwd')).cwdReadableByDaemon).toBeUndefined()
+  })
+
+  it('omits the verdict on attach to an existing session', async () => {
+    await create('attach', process.cwd())
+    const attached = await create('attach', process.cwd())
+    expect(attached.isNew).toBe(false)
+    expect(attached.cwdReadableByDaemon).toBeUndefined()
+  })
+})

src/main/daemon/terminal-host-session-create.ts

@@ -1,3 +1,4 @@
+import { accessSync, constants as fsConstants } from 'node:fs'
 import { buildStartupCommandSubmission } from '../../shared/startup-command-submission'
 import { resolvePtyOwnerBackend } from '../../shared/pty-owner-backend'
 import { getDaemonSessionResultMetadata } from './daemon-create-or-attach-result'
@@ -88,6 +89,8 @@ async function spawnAndPublishSession(
   ctx: { size: { cols: number; rows: number }; wslDistro: string | undefined }
 ): Promise<CreateOrAttachResult> {
   const { size, wslDistro } = ctx
+  // Why before the fork: the shell's own cwd may already have fallen back, so probe the requested path.
+  const cwdReadableByDaemon = opts.cwd && !wslDistro ? isCwdReadableByThisProcess(opts.cwd) : null
   const subprocess = await deps.spawnSubprocess({
     sessionId: opts.sessionId,
     cols: size.cols,
@@ -184,6 +187,20 @@ async function spawnAndPublishSession(
     shellState: session.shellState,
     incarnationId: session.incarnationId,
     ...getDaemonSessionResultMetadata(session),
+    ...(cwdReadableByDaemon !== null ? { cwdReadableByDaemon } : {}),
     attachToken: token
   }
 }
+
+// Why R_OK|X_OK: listing a directory needs read, and entering it needs search — both are what
+// TCC withholds. A non-permission failure (ENOENT, ENOTDIR) reads as readable so it can never
+// masquerade as a permission denial.
+function isCwdReadableByThisProcess(cwd: string): boolean {
+  try {
+    accessSync(cwd, fsConstants.R_OK | fsConstants.X_OK)
+    return true
+  } catch (error) {
+    const code = (error as NodeJS.ErrnoException).code
+    return code !== 'EACCES' && code !== 'EPERM'
+  }
+}

src/main/ipc/telemetry.ts

@@ -24,7 +24,9 @@ let storeRef: Store | null = null
 
 const MAIN_OWNED_TELEMETRY_EVENTS = new Set<EventName>([
   'app_starred_orca',
+  'daemon_adopted',
   'daemon_audit_eligibility',
+  'daemon_pty_cwd_denied',
   'star_nag_outcome',
   'feature_interaction_usage_bucket_reached'
 ])

src/shared/daemon-adoption-telemetry.test.ts

@@ -0,0 +1,89 @@
+import { describe, expect, it } from 'vitest'
+import { classifyDaemonPtyCwd, classifyDaemonSpawnerPath } from './daemon-adoption-telemetry'
+import { eventSchemas } from './telemetry-event-registry'
+
+describe('classifyDaemonSpawnerPath', () => {
+  const alwaysExists = () => true
+
+  it('classifies the installed app, the ShipIt staging area, and everything else', () => {
+    expect(
+      classifyDaemonSpawnerPath('/Applications/Orca.app/Contents/MacOS/Orca', alwaysExists)
+    ).toBe('applications')
+    expect(
+      classifyDaemonSpawnerPath('/private/Applications/Orca.app/Contents/MacOS/Orca', alwaysExists)
+    ).toBe('applications')
+    expect(
+      classifyDaemonSpawnerPath(
+        '/Users/a/Library/Caches/com.stablyai.orca.ShipIt/update.abc/Orca.app/Contents/MacOS/Orca',
+        alwaysExists
+      )
+    ).toBe('updater-cache')
+    expect(
+      classifyDaemonSpawnerPath('/Users/a/Applications/Orca.app/Contents/MacOS/Orca', alwaysExists)
+    ).toBe('other')
+    expect(classifyDaemonSpawnerPath('/tmp/OrcaA.app/Contents/MacOS/Orca', alwaysExists)).toBe(
+      'other'
+    )
+  })
+
+  it('reports a deleted spawner as missing and an unrecorded one as unknown', () => {
+    expect(
+      classifyDaemonSpawnerPath('/Applications/Orca.app/Contents/MacOS/Orca', () => false)
+    ).toBe('missing')
+    expect(classifyDaemonSpawnerPath(null, alwaysExists)).toBe('unknown')
+  })
+})
+
+describe('classifyDaemonPtyCwd', () => {
+  it('maps the TCC-protected home folders and separates the rest of home from outside it', () => {
+    expect(classifyDaemonPtyCwd('/Users/a/Documents/repo', '/Users/a')).toBe('documents')
+    expect(classifyDaemonPtyCwd('/Users/a/Desktop', '/Users/a/')).toBe('desktop')
+    expect(classifyDaemonPtyCwd('/Users/a/Downloads/x/y', '/Users/a')).toBe('downloads')
+    expect(classifyDaemonPtyCwd('/Users/a/projects/repo', '/Users/a')).toBe('other-home')
+    expect(classifyDaemonPtyCwd('/Users/a', '/Users/a')).toBe('other-home')
+    expect(classifyDaemonPtyCwd('/Volumes/ext/repo', '/Users/a')).toBe('outside-home')
+    // A sibling home that merely shares the prefix is not inside this home.
+    expect(classifyDaemonPtyCwd('/Users/ab/Documents', '/Users/a')).toBe('outside-home')
+  })
+})
+
+// Privacy invariant: enum-only. A raw path, version, or exact count must be rejected by .strict().
+describe('daemon_adopted / daemon_pty_cwd_denied schemas', () => {
+  const adopted = {
+    app_version_match: 'different',
+    spawner_path_class: 'updater-cache',
+    tcc_attribution: 'intact',
+    live_session_count_bucket: '2-5'
+  }
+  const denied = {
+    cwd_class: 'documents',
+    app_version_match: 'different',
+    spawner_path_class: 'updater-cache'
+  }
+
+  it('accepts the enum payloads', () => {
+    expect(eventSchemas.daemon_adopted.safeParse(adopted).success).toBe(true)
+    expect(eventSchemas.daemon_pty_cwd_denied.safeParse(denied).success).toBe(true)
+  })
+
+  it('rejects leaked paths, versions, counts, and unknown enum values', () => {
+    for (const leak of [
+      { spawner_exec_path: '/Users/alice/Library/Caches/ShipIt/Orca.app' },
+      { app_version: '1.4.187' },
+      { live_session_count: 3 },
+      { cwd: '/Users/alice/Documents' }
+    ]) {
+      expect(eventSchemas.daemon_adopted.safeParse({ ...adopted, ...leak }).success).toBe(false)
+      expect(eventSchemas.daemon_pty_cwd_denied.safeParse({ ...denied, ...leak }).success).toBe(
+        false
+      )
+    }
+    expect(
+      eventSchemas.daemon_adopted.safeParse({ ...adopted, spawner_path_class: '/Applications' })
+        .success
+    ).toBe(false)
+    expect(
+      eventSchemas.daemon_pty_cwd_denied.safeParse({ ...denied, cwd_class: 'Documents' }).success
+    ).toBe(false)
+  })
+})

src/shared/daemon-adoption-telemetry.ts

@@ -0,0 +1,67 @@
+// Enums for the `daemon_adopted` and `daemon_pty_cwd_denied` telemetry events (#17696).
+// Both exist to measure how often a macOS app runs on a daemon left behind by an earlier app
+// bundle, and how often such a daemon actually spawns a terminal whose cwd it cannot read.
+// Enum-only: no paths, versions, or exact counts ever reach the wire.
+
+/** How the adopted daemon's recorded app version compares to the running app. */
+export const DAEMON_ADOPTED_APP_VERSION_MATCH = ['same', 'different', 'unknown'] as const
+export type DaemonAdoptedAppVersionMatch = (typeof DAEMON_ADOPTED_APP_VERSION_MATCH)[number]
+
+/**
+ * Where the binary that forked the adopted daemon lives now. `updater-cache` is the Squirrel
+ * ShipIt staging area — a daemon attributed there is the reported #17696 shape.
+ */
+export const DAEMON_SPAWNER_PATH_CLASSES = [
+  'applications',
+  'updater-cache',
+  'other',
+  'missing',
+  'unknown'
+] as const
+export type DaemonSpawnerPathClass = (typeof DAEMON_SPAWNER_PATH_CLASSES)[number]
+
+export const DAEMON_TCC_ATTRIBUTION_VALUES = ['intact', 'severed', 'unknown'] as const
+
+/** Which macOS-protected folder class the denied cwd falls under. */
+export const DAEMON_PTY_CWD_CLASSES = [
+  'documents',
+  'desktop',
+  'downloads',
+  'other-home',
+  'outside-home'
+] as const
+export type DaemonPtyCwdClass = (typeof DAEMON_PTY_CWD_CLASSES)[number]
+
+export function classifyDaemonSpawnerPath(
+  spawnerExecPath: string | null,
+  exists: (path: string) => boolean
+): DaemonSpawnerPathClass {
+  if (!spawnerExecPath) {
+    return 'unknown'
+  }
+  if (!exists(spawnerExecPath)) {
+    return 'missing'
+  }
+  if (/\/Library\/Caches\/[^/]*ShipIt\//.test(spawnerExecPath)) {
+    return 'updater-cache'
+  }
+  return /^(?:\/private)?\/Applications\//.test(spawnerExecPath) ? 'applications' : 'other'
+}
+
+export function classifyDaemonPtyCwd(cwd: string, homeDir: string): DaemonPtyCwdClass {
+  const home = homeDir.replace(/\/+$/, '')
+  if (!home || !(cwd === home || cwd.startsWith(`${home}/`))) {
+    return 'outside-home'
+  }
+  const topLevel = cwd.slice(home.length + 1).split('/')[0]
+  switch (topLevel) {
+    case 'Documents':
+      return 'documents'
+    case 'Desktop':
+      return 'desktop'
+    case 'Downloads':
+      return 'downloads'
+    default:
+      return 'other-home'
+  }
+}

src/shared/telemetry-daemon-event-schemas.ts

@@ -14,6 +14,12 @@ import {
   DAEMON_AUDIT_TRIGGER_VALUES,
   DAEMON_EVIDENCE_SOURCE_VALUES
 } from './daemon-audit-eligibility'
+import {
+  DAEMON_ADOPTED_APP_VERSION_MATCH,
+  DAEMON_PTY_CWD_CLASSES,
+  DAEMON_SPAWNER_PATH_CLASSES,
+  DAEMON_TCC_ATTRIBUTION_VALUES
+} from './daemon-adoption-telemetry'
 import { errorClassSchema, settingsChangedKeySchema } from './telemetry-property-schemas'
 
 // Why: daemon start-failure signal (fleet-wide outage like v1.4.129-rc.1); enum-only so raw stderr never reaches the wire.
@@ -50,6 +56,27 @@ export const mainThreadHangDetectedSchema = z
   })
   .strict()
 
+// Why: #17696 — a macOS app adopting a daemon from an earlier bundle is invisible to
+// `daemon_lifecycle` (nothing is replaced). Once per macOS launch that adopts; enum-only.
+export const daemonAdoptedSchema = z
+  .object({
+    app_version_match: z.enum(DAEMON_ADOPTED_APP_VERSION_MATCH),
+    spawner_path_class: z.enum(DAEMON_SPAWNER_PATH_CLASSES),
+    tcc_attribution: z.enum(DAEMON_TCC_ATTRIBUTION_VALUES),
+    live_session_count_bucket: z.enum(DAEMON_LIFECYCLE_SESSION_BUCKETS)
+  })
+  .strict()
+
+// Why: the #17696 symptom itself — the daemon spawned a terminal into a cwd it cannot read while
+// the app can. Emitted only on that proven divergence, so a missing or app-unreadable cwd never counts.
+export const daemonPtyCwdDeniedSchema = z
+  .object({
+    cwd_class: z.enum(DAEMON_PTY_CWD_CLASSES),
+    app_version_match: z.enum(DAEMON_ADOPTED_APP_VERSION_MATCH),
+    spawner_path_class: z.enum(DAEMON_SPAWNER_PATH_CLASSES)
+  })
+  .strict()
+
 // Why: daemon replace/retire lifecycle signal — issue #7936 was undiagnosable without asking a user for daemon.log.
 // Enum-only + bucketed session count so no paths, raw versions, or exact counts reach the wire.
 // The union keeps each reason pinned to its transition, so a death can't be reported as a replace.

src/shared/telemetry-event-registry.ts

@@ -14,8 +14,10 @@ import {
   agentHookTransportBlockedSchema,
   agentHookUnattributedSchema,
   codexTrustGrantSchema,
+  daemonAdoptedSchema,
   daemonAuditEligibilitySchema,
   daemonLifecycleSchema,
+  daemonPtyCwdDeniedSchema,
   daemonStartFailedSchema,
   mainThreadHangDetectedSchema,
   remoteOutboundBudgetCloseSchema,
@@ -122,6 +124,8 @@ export const eventSchemas = {
   daemon_start_failed: daemonStartFailedSchema,
   main_thread_hang_detected: mainThreadHangDetectedSchema,
   daemon_lifecycle: daemonLifecycleSchema,
+  daemon_adopted: daemonAdoptedSchema,
+  daemon_pty_cwd_denied: daemonPtyCwdDeniedSchema,
   daemon_audit_eligibility: daemonAuditEligibilitySchema,
   runtime_rpc_start_failed: runtimeRpcStartFailedSchema,
   remote_outbound_budget_close: remoteOutboundBudgetCloseSchema,