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[BUG] VS Code Extension v2.0.75 Sign In button does nothing - OAuth flow not triggered on macOS #16505

Description

@firearch

Preflight Checklist

  • I have searched existing issues and this hasn't been reported yet
  • This is a single bug report (please file separate reports for different bugs)
  • I am using the latest version of Claude Code

What's Wrong?

"VS Code extension v2.0.75 - Sign In button doesn't trigger OAuth flow on macOS"

Description

When clicking the "Sign In" button in the Claude Code VS Code extension, nothing happens. No browser window opens, and no authentication flow is initiated. The button just displays "Signing in..." indefinitely without any action.

Actual Behavior

  • Button changes to "Signing in..." state
  • No browser window opens
  • No authentication URL is logged
  • Button remains stuck in "Signing in..." state
  • No error messages are shown to the user

Environment

  • OS: macOS Sequoia 15.1 (Darwin 25.1.0)
  • VS Code Version: [Latest stable]
  • Claude Code Extension Version: 2.0.75 (darwin-arm64)
  • Architecture: Apple Silicon (ARM64)

What Should Happen?

Expected Behavior

  • Browser should open to https://claude.ai or authentication URL
  • OAuth flow should complete
  • User should be signed in to the extension

Error Messages/Logs

Logs

  Output Panel (Claude Code):
  2026-01-06 12:46:32.422 [info] Getting authentication status
  2026-01-06 12:46:32.423 [info] Keychain read failed, trying file fallback
  2026-01-06 12:46:32.423 [info] No authentication found
  2026-01-06 12:46:32.443 [info] Received message from webview: {"type":"launch_claude","channelId":"3m980o0twsx"...}
  2026-01-06 12:46:32.445 [info] Launching Claude on channel: 3m980o0twsx

  Note: After clicking "Sign In", no additional logs appear - no OAuth URL, no browser open attempt, nothing.

  Developer Console also shows:
  notificationsAlerts.ts:42 An OS keyring couldn't be identified for storing the encryption related data in your current desktop environment.

  Additional Context

  - The keychain access warning appears, suggesting possible macOS keychain permissions issue
  - CLI authentication works perfectly: Running /login in the Claude Code CLI successfully opens a browser and completes authentication
  - This appears to be specific to the VS Code extension UI, not the underlying authentication system
  - Issue persists after:
    - Restarting VS Code
    - Clearing VS Code cache
    - Signing out and attempting to sign in again
    - Reinstalling the extension

Steps to Reproduce

Steps to Reproduce

  1. Install Claude Code extension v2.0.75 in VS Code
  2. Open the Claude Code panel
  3. Click the "Sign In" button
  4. Observe: Button shows "Signing in..." but no browser opens
  5. Check Output panel → "Claude Code" - no authentication attempt is logged

Claude Model

Not sure / Multiple models

Is this a regression?

Yes, this worked in a previous version

Last Working Version

No response

Claude Code Version

VS Code extension v2.0.75

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

VS Code integrated terminal

Additional Information

No response

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