[BUG] Bypass mode ignores blanket file authorization (Desktop, macOS) — prompts continue despite both settings

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?

Environment:

Desktop (macOS)
Permission Mode: Bypass
Explicit blanket authorization: "I authorize read access to all files in [project directory]"

Steps to reproduce:

Enable Bypass permission mode
Grant explicit blanket file authorization via dialog
Run a task requiring multiple file read/write operations

Expected:
No approval prompts (both bypass mode and blanket auth should suppress them)

Actual:
11+ approval prompts continue despite both settings enabled

Impact:
Makes the session unusable; slower than ChatGPT. Approval system appears to ignore both bypass mode and explicit blanket authorization.

What Should Happen?

Immediate (bug fix):
Bypass mode + explicit blanket file authorization should prevent approval prompts entirely. A user who has explicitly authorized read/write access to a directory should not be re-prompted for the same operations.

Longer-term (feature request):
Beyond bypass mode, there should be a granular permission level that allows users to approve read/write access to a specific directory tree (e.g., ~/Documents/Source\ Code/Utilities) without granting full disk access. This would:

Eliminate repeated prompts for normal dev workflow within that scope
Maintain security by blocking access to sensitive areas (home, /etc, etc.)
Split the difference between "approve everything" (bypass) and "approve every file op" (current)

Example: Approve ~/Documents/Source\ Code/Utilities/** for read/write, but not ~/.ssh, ~/.aws, etc.

Error Messages/Logs

Steps to Reproduce

1. Set up Claude Code Desktop with typical development workflow (file reads/writes to project directory)
2. Over the course of normal usage across multiple coding sessions and requests (months), observe approval prompts
3. Even when bypass mode is enabled or blanket file authorization has been granted, each new coding request generates 5+ approval prompts
4. Approve each prompt; prompts continue on the next request
5. Repeat across multiple projects and sessions

Observed pattern: Approval prompts are not persisting across sessions, and even within a single task, repeated approvals for the same authorization (bypass mode, blanket file auth) do not suppress subsequent prompts.

Claude Model

Not sure / Multiple models

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

Claude 2.2553.1 (c38127) 2026-09-18T00:41:58.000Z

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

_No response_