[Cowork] "Always allow" permission prompts not persisting — reads and writes — v1.1617.0

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?

In Claude Desktop Cowork, permission prompts appear for every file read and write operation. Clicking "Always allow" does not persist — the prompt reappears on the very next file operation, even within the same session. This affects both reads and writes, not just edits.

What Should Happen?

Clicking "Always allow" should suppress further permission prompts for that file/operation type for the duration of the session at minimum.

Error Messages/Logs

Steps to Reproduce

1. Open Claude Desktop and start a Cowork session
2. Point Cowork at a project folder (e.g. Documents/Cowork/Projects)
3. Ask Claude to read or write any file in that folder
4. Click "Always allow" on the permission prompt
5. Ask Claude to perform the next file operation
6. Observe: permission prompt appears again immediately
7. Repeat indefinitely — prompts never stop appearing

Claude Model

Sonnet (default)

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

1.1617.0 (build 8d6345, 2026-04-09T16:10:15.000Z) — Claude Desktop

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

This is occurring in Claude Desktop Cowork, not Claude Code CLI. macOS system-level folder permissions are correctly granted (System Settings → Privacy & Security → Files and Folders → Claude has Desktop and Documents access toggled on). This is not an OS permission issue. Confirmed on latest available version — app reports "You are running the latest version." Related to issue #37814 but also affects file reads, not just writes.