[BUG] "Allow all edits in this session" doesn't persist - Edit tool keeps asking for permission

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?

When using the Edit tool, even after selecting "Allow all edits in this session" (Shift+Tab), Claude Code continues to ask for permission on every subsequent Edit operation within the same session.

Expected Behavior:

1. First Edit operation in a session → Claude asks for permission
2. 2. User selects "Allow all edits in this session" (Shift+Tab)
3. 3. All subsequent Edit operations in that session → Should NOT ask for permission again

Actual Behavior:

1. First Edit operation → Claude asks for permission ✓
2. 2. User selects "Allow all edits in this session" (Shift+Tab) ✓
3. 3. Next Edit operation → Claude asks for permission again ✗
4. 4. This continues for every single Edit operation (e.g., 100 edits = 100 permission prompts)

Settings Configuration:
The Edit tool is correctly in the "ask" list in settings.json:

"permissions": {
  "ask": [
    "Edit",
    "Bash(rm:*)",
    "Bash(mv:*)",
    "Bash(git push:*)"
  ]
}

Impact:
This makes batch editing workflows extremely tedious, requiring manual approval for every single edit even after explicitly granting session-level permission.

What Should Happen?

After selecting "Allow all edits in this session", the session-level permission should be remembered and Claude should proceed with all subsequent Edit operations automatically without asking for permission again until the session ends or Claude Code is restarted.

Error Messages/Logs

Steps to Reproduce

1. Add "Edit" to the "ask" list in ~/.claude/settings.json:
2. ```json
3. "permissions": {
4. "ask": [
5. "Edit",
6. "Bash(rm:*)",
7. "Bash(mv:*)",
8. "Bash(git push:*)"
9. ]
10. }
11. ```
12. Start Claude Code and request it to perform multiple Edit operations (e.g., "Make 5 small edits to this file")
13. On the first Edit operation, Claude will ask for permission
14. Select "Allow all edits in this session" (press Shift+Tab)
15. Observe: The next Edit operation will ask for permission again
16. Repeat: Every subsequent Edit operation continues to ask for permission, despite having granted session-level permission

Claude Model

None

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

2.1.27 (Claude Code)

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

_No response_