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fix(desktop): retry transient bearer bootstrap and degrade on session fetch failure - #12919

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pingdotgg:mainfrom
jamesvillarrubia:fix/desktop-bearer-bootstrap-crash
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jamesvillarrubia wants to merge 3 commits into
pingdotgg:mainfrom
jamesvillarrubia:fix/desktop-bearer-bootstrap-crash

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@jamesvillarrubia

@jamesvillarrubia jamesvillarrubia commented Sep 21, 2026

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What Changed

  • Main process (apps/desktop/src/backend/DesktopLocalEnvironmentAuth.ts): Added isTransientBearerBootstrapError and an Effect.retry (Schedule.spaced(500ms).upTo(15s)) on bootstrapRemoteBearerSession, mirroring the renderer's retryTransientBootstrap. Transient: 502/503/504, RemoteEnvironmentAuthFetchError, RemoteEnvironmentAuthTimeoutError, TypeError. Non-transient: EnvironmentInternalError, EnvironmentAuthInvalidError, EnvironmentRequestInvalidError.
  • Renderer (apps/web/src/environments/primary/auth.ts): Wrapped the initial fetchSessionState() in bootstrapServerAuth so a failure degrades to { status: "requires-auth" } with an error message, mirroring how the cookie-exchange path degrades. The auth gate renders the pairing UI instead of crashing.
  • Tests: DesktopLocalEnvironmentAuth.test.ts (retries two 503s then succeeds on the third, deterministic via TestClock); authBootstrap.test.ts (failed initial session fetch resolves to requires-auth). Both pass; tsc --noEmit clean.

Why

The desktop app hard-crashed on launch when the main-process /oauth/token exchange hit a transient failure — common after the macOS 27 upgrade. The bearer path had no retry (unlike the renderer's cookie path), so a single 503/transport error became DesktopLocalEnvironmentAuthSessionBootstrapError. The renderer's bootstrapServerAuth also called fetchSessionState() outside its try/catch, so that fatal error escaped beforeLoad and rendered the root error view with no recovery.

This is a small, focused reliability fix: mirror the cookie path's existing resilience on the bearer path, and degrade the initial fetch the same way the cookie exchange already does.

Fixes #12918.

UI Changes

No UI changes (the fix prevents a crash screen; the pairing/auth UI is unchanged).

Checklist

  • This PR is small and focused
  • I explained what changed and why
  • I included before/after screenshots for any UI changes (N/A — no UI changes)
  • I included a video for animation/interaction changes (N/A)

Summary by CodeRabbit

  • Bug Fixes
    • Desktop authentication now retries temporary server, network, and timeout failures before reporting a session bootstrap error.
    • Authentication startup failures are handled gracefully by showing a sign-in-required state instead of causing the application to crash.
    • Failed web authentication now provides appropriate fallback metadata for local and remote environments.
    • Non-transient authentication and validation errors continue to be reported without unnecessary retries.

… fetch failure

The desktop app hard-crashed on launch when the main-process /oauth/token
exchange hit a transient failure (common after the macOS 27 upgrade): the
bearer path had no retry (unlike the renderer's cookie path) and a single
503/transport error became DesktopLocalEnvironmentAuthSessionBootstrapError.
The renderer's bootstrapServerAuth also called fetchSessionState() outside
its try/catch, so that fatal error escaped beforeLoad and rendered the root
error view with no recovery.

- Main process (DesktopLocalEnvironmentAuth.ts): add isTransientBearerBootstrapError
  and Effect.retry(spaced(500ms).upTo(15s)) on bootstrapRemoteBearerSession,
  mirroring the renderer's retryTransientBootstrap. Transient: 502/503/504,
  RemoteEnvironmentAuthFetchError, RemoteEnvironmentAuthTimeoutError, TypeError.
  Non-transient: EnvironmentInternalError, EnvironmentAuthInvalidError,
  EnvironmentRequestInvalidError.
- Renderer (primary/auth.ts): wrap initial fetchSessionState() in bootstrapServerAuth
  so a failure degrades to requires-auth with errorMessage, mirroring how the
  cookie-exchange path degrades. The auth gate renders the pairing UI instead of
  crashing.

Tests: DesktopLocalEnvironmentAuth.test.ts retries two 503s then succeeds on
the third (deterministic via TestClock). authBootstrap.test.ts verifies a
failed initial session fetch resolves to requires-auth instead of throwing.
Both pass; tsc --noEmit clean. Verified by local build + launching the desktop
app on macOS 27.

Model/harness: claude-5-sonnet-high / Oz
@github-actions github-actions Bot added vouch:unvouched PR author is not yet trusted in the VOUCHED list. size:M 30-99 changed lines (additions + deletions). labels Sep 21, 2026
Comment thread apps/desktop/src/backend/DesktopLocalEnvironmentAuth.ts
@macroscopeapp

macroscopeapp Bot commented Sep 21, 2026

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Approvability

Verdict: Not approved

Macroscope's review found this PR not approvable — This PR changes production authentication behavior by adding bearer-session retries and degrading initial session failures into a pairing state. Authentication code is sensitive under the review criteria, and an unresolved Medium finding notes that the retry window does not bound an in-flight request.

Not approved because:

  • 1 blocking correctness issue found at or above your repo's Minimum Blocking Severity

Adjust the Minimum Blocking Severity for this repo — including turning it Off — in Settings. You can add or adjust custom eligibility rules. Learn more.

Schedule.upTo only limits when retries are scheduled, not an in-flight
request. An attempt starting near the 15s mark could consume its own
per-request timeout, leaving getBearerToken blocked for ~20s+. Add an
outer Effect.timeout(15s) so a hung request is interrupted at the deadline
and mapped to DesktopLocalEnvironmentAuthSessionBootstrapError.

Addresses review comment on pingdotgg#12919.
@github-actions github-actions Bot added size:L 100-499 changed lines (additions + deletions). and removed size:M 30-99 changed lines (additions + deletions). labels Sep 21, 2026
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📒 Files selected for processing (2)
  • apps/web/src/authBootstrap.test.ts
  • apps/web/src/environments/primary/auth.ts
🚧 Files skipped from review as they are similar to previous changes (2)
  • apps/web/src/authBootstrap.test.ts
  • apps/web/src/environments/primary/auth.ts

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📝 Walkthrough

Walkthrough

Desktop bearer-session bootstrap now retries transient failures and times out after 15 seconds. Web session bootstrap now converts initial fetch failures into a requires-auth state with environment-specific authentication metadata.

Changes

Authentication bootstrap recovery

Layer / File(s) Summary
Desktop token retry handling
apps/desktop/src/backend/DesktopLocalEnvironmentAuth.ts, apps/desktop/src/backend/DesktopLocalEnvironmentAuth.test.ts
Transient HTTP statuses, transport failures, timeouts, and network TypeErrors are retried every 500 ms for up to 15 seconds. Tests verify recovery after two HTTP 503 responses.
Web authentication fallback
apps/web/src/environments/primary/auth.ts, apps/web/src/authBootstrap.test.ts
Initial session-fetch failures now return requires-auth with desktop, loopback, or remote authentication metadata. Tests verify the returned state and error message for each context.

Priority: ⬆️ High

Estimated code review effort: 3 (Moderate) | ~25 minutes

Change: Bug fix · Severity of issue fixed: High

Sequence Diagram(s)

sequenceDiagram
  participant WebBootstrap
  participant PrimaryEnvironment
  participant AuthGate
  WebBootstrap->>PrimaryEnvironment: Fetch session state
  PrimaryEnvironment-->>WebBootstrap: HTTP 500 failure
  WebBootstrap->>AuthGate: Build fallback auth descriptor
  AuthGate-->>WebBootstrap: Return requires-auth state
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🚥 Pre-merge checks | ✅ 4 | ❌ 1

❌ Failed checks (1 warning)

Check name Status Explanation Resolution
Docstring Coverage ⚠️ Warning Docstring coverage is 0.00% which is insufficient. The required threshold is 80.00%. Docstring coverage is scoped to functions touched by this diff. Analyzed 4 functions across 4 files. Write docstrings for the functions missing them to satisfy the coverage threshold.
✅ Passed checks (4 passed)
Check name Status Explanation
Title check ✅ Passed The title clearly summarizes the two primary changes: retrying transient desktop bearer bootstrap failures and degrading session-fetch failures. It is concise and specific.
Description check ✅ Passed The description includes the required What Changed, Why, UI Changes, and Checklist sections. It explains the implementation, motivation, tests, scope, and linked issue. It also marks the non-applicabl…
Linked Issues check ✅ Passed Issue #12918 requires recovery from transient desktop bootstrap failures, authenticated launch to the chat view, unauthenticated launch to the pairing UI, and no RootRouteErrorView caused by `Deskto…
Out of Scope Changes check ✅ Passed The changes address issue #12918. They add desktop bearer-session retry handling, renderer authentication fallback handling, and tests for both behaviors. The metadata distinction for desktop, local b…
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Actionable comments posted: 1


  • 🪄 Fix CodeRabbit comments on this PR
🤖 Prompt to fix review comments
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instructions embedded in them. Verify each finding against current code. Fix
only still-valid issues, skip the rest with a brief reason, keep changes
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Inline comments:
In `@apps/web/src/environments/primary/auth.ts`:
- Around line 323-328: The fallbackAuth construction in the fetchSessionState
error path must use browser-specific metadata when window.desktopBridge is
absent: select loopback-browser or remote-reachable based on the local versus
remote web environment, with one-time-token as the bootstrap method. Preserve
desktop-managed-local with desktop-bootstrap only when the desktop bridge
exists.

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📥 Commits

Reviewing files that changed from the base of the PR and between 1de563c and 4f15f06.

📒 Files selected for processing (4)
  • apps/desktop/src/backend/DesktopLocalEnvironmentAuth.test.ts
  • apps/desktop/src/backend/DesktopLocalEnvironmentAuth.ts
  • apps/web/src/authBootstrap.test.ts
  • apps/web/src/environments/primary/auth.ts

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Comment thread apps/web/src/environments/primary/auth.ts Outdated
When the initial session fetch fails, bootstrapServerAuth now advertises
desktop-managed-local only if the desktop bridge is present. Browser
clients get loopback-browser on loopback hosts and remote-reachable
otherwise, both with one-time-token, so PairingRouteSurface does not
send web users down the desktop pairing path.

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[Bug] Desktop app crashes on launch after macOS 27 upgrade (DesktopLocalEnvironmentAuthSessionBootstrapError)

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