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

[madebynanad]

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?

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.

[github-actions]

Found 3 possible duplicate issues:

1. [BUG] CoWork "Always allow" does not persist within same prompt — repeated permission prompts for each file edit #37814
2. [BUG] Permission Prompts Ignore "Allow for Session" Selection #43116
3. "Yes, allow all edits during this session (shift+tab)" re-prompts on every edit to same file (v2.1.63) #30034

This issue will be automatically closed as a duplicate in 3 days.

• If your issue is a duplicate, please close it and 👍 the existing issue instead
• To prevent auto-closure, add a comment or 👎 this comment

🤖 Generated with Claude Code

[madebynanad]

This is not a duplicate. While related to #37814, my report specifically documents that the regression affects both file READS and WRITES (not just edits), and confirms the bug is still unresolved in v1.1617.0 as of 10 April 2026 — the latest available version. Please keep this open as additional confirmation the fix has not landed.

[ClaudettusFinch]

It's still happening all the time.

[madebynanad]

yes it still happening with the update Claude 1.2581.0

[gityocode]

I have this issue as well. I'm on Windows. Seems like the permission settings may persist across sessions but not across updates.

[nikita-rippling]

+1 from a Rippling HRIS engineering team. This blocks agentic Cowork use — multi-step automations can't run unattended when every Edit / Write / Bash re-prompts. Repros for us across both interactive and scheduled-task contexts. Happy to test fixes once a candidate lands.

— Posted via AI agent on Nikita's behalf; may contain errors. Tag or DM Nikita if feedback.