[BUG][Windows] Desktop app ignores defaultMode: bypassPermissions in settings.json — mode picker missing "Bypass permissions" option

Preflight Checklist

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

What's Wrong?

The Claude Code Desktop app on Windows has two related problems with bypass permissions:

1. The in-session mode picker only shows three options: "Ask permissions", "Accept edits", and "Plan mode". "Bypass permissions" is not available as an option in the GUI at all.
2. Setting defaultMode: "bypassPermissions" in ~/.claude/settings.json has no effect — the session still starts in "Ask permissions" mode and the settings file is silently ignored.

What Should Happen?

Bypass permissions should either appear as a fourth option in the mode picker, or be respected from ~/.claude/settings.json so sessions start without confirmation prompts. The CLI flag --dangerously-skip-permissions works correctly, so the underlying feature exists — it just needs to be exposed in the Desktop GUI on Windows.

Error Messages/Logs

No error message shown. The app silently ignores the setting and defaults to "Ask permissions" mode without any warning or fallback notification.

Steps to Reproduce

1. Open Claude Code Desktop app on Windows 11
2. Add "defaultMode": "bypassPermissions" to ~/.claude/settings.json under permissions
3. 3. Start a new session
4. 4. Observe: session starts in "Ask permissions" mode — settings.json is ignored

Alternatively:

1. Open Claude Code Desktop app on Windows 11
2. 2. Click the mode picker at the bottom of the session pane
3. 3. Observe: only three options appear — "Ask permissions", "Accept edits", "Plan mode"
4. 4. "Bypass permissions" is not listed as an option

Claude Model

None

Is this a regression?

No, this never worked

Last Working Version

_No response_

Claude Code Version

2.1.143 (Claude Code)

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

PowerShell

Additional Information

Related issues on macOS (same problem, different platform):

• #55095 — Bypass permissions mode missing from session UI on Mac
• - #29026 — Desktop app ignores settings.json defaultMode on Mac
• - - #42428 — Bypass permissions non-functional in Desktop App on Mac

This Windows report confirms the issue is cross-platform.