[BUG] Desktop: Bypass Permissions mode can't be enabled on macOS — reverts to Accept Edits, "Permission mode couldn't be changed" (2.1.148)

[prudentmildew]

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?

Bypass Permissions mode cannot be activated in the Claude Code Desktop app even though "Allow bypass permissions mode" is enabled in Settings → Claude Code.

New sessions start in Accept Edits with the banner "Bypass Permissions mode isn't enabled. The session started in Accept Edits - enable Bypass Permissions in Settings to use it."

Attempting to switch the mode manually fails with the toast "Permission mode couldn't be changed. You can try again," and any mode change reverts to Accept Edits after the first prompt.

The same bypass workflow works correctly in the Claude Code CLI (--dangerously-skip-permissions) on the same machine, so this is Desktop-specific.

What Should Happen?

With the setting enabled, a new session can enter Bypass Permissions and stay there.

Error Messages/Logs

Bypass Permissions mode isn't enabled. The session started in Accept Edits - enable Bypass Permissions in Settings to use it.

Permission mode couldn't be changed. You can try again

Steps to Reproduce

1. Open Claude Code Desktop (embedded Claude Code 2.1.148), macOS.
2. Settings → Claude Code → enable "Allow bypass permissions mode".
3. Fully quit (⌘Q) and relaunch.
4. Start a new session → banner reports bypass isn't enabled; session opens in Accept Edits.
5. Try to switch to Bypass Permissions via the mode selector / Shift+Tab.
6. Toast appears: "Permission mode couldn't be changed. You can try again." Mode stays on / reverts to Accept Edits after the first prompt.

Claude Model

Opus

Is this a regression?

Yes, this worked in a previous version

Last Working Version

No response

Claude Code Version

2.1.148

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

Environment

• Claude Code: 2.1.148 (embedded in Desktop app)
• Desktop app version: Claude for Mac1.8555.0 (8245b7) 2026-05-21T05:49:11.000Z
• Platform: Claude Code Desktop (macOS app)
• OS: macOS 26.4.1 (25E253)
• Plan: Max
• CLI comparison: bypass works via claude --dangerously-skip-permissions on the same machine

[LikeDreamwalker]

same issue here and I am windows 11

[dnikolayev]

Can confirm the same on mac os, Claude 1.8555.1 (cfe7d4) 2026-05-22T17:41:12.000Z

[martinkallstrom]

Confirmed. Fresh install, fresh macos 26.4 (25E246), Claude 1.8555.2 (a476c3) 2026-05-22T23:04:37.000Z

[souviik]

This issue requires immediate attention and resolution. Confirmed issue on Windows

[kticoder]

I have the same problem on my Mac.

[alsift]

Confirming this on macOS with the same version same symptoms exactly.

"Bypass Permissions mode isn't enabled. The session started in Accept Edits — enable Bypass Permissions in Settings to use it."

[hamzarabi3]

Confirming same issue on MacOS, Immediate attention needed.