[BUG] Cowork: file delete permission dialog never appears in both "Ask before acting" and "Act without asking" modes (Windows)

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 Claude (Cowork mode) attempts to delete a file in a mounted workspace folder,
the deletion permission dialog never appears. This happens in both permission modes:

• "Ask before acting" — no dialog shown
• "Act without asking" — no dialog shown (per docs, deletion should still always prompt in this mode)

The allow_cowork_file_delete tool call fails silently, so files can never be
deleted through Cowork.

What Should Happen?

A permission dialog should appear asking the user to Allow or Deny the deletion,
regardless of the selected mode. Deletion should proceed only after clicking "Allow",
as described in the official docs ("In both modes, Claude will still ask before
permanently deleting files").

Error Messages/Logs

No dialog is ever rendered. The tool returns a denial immediately
(same pattern as #46788: `Permission to use mcp__cowork__allow_cowork_file_delete has been denied`).

Steps to Reproduce

1. Open Cowork in Claude Desktop on Windows
2. Grant folder access to a local workspace folder
3. Ask Claude to delete a file in that folder
4. Claude calls allow_cowork_file_delete
5. No permission dialog appears; the call is denied silently
6. Switch mode ("Ask before acting" ↔ "Act without asking") and repeat — same result

Claude Model

Not sure / Multiple models

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

Claude 1.18286.0 (259c3f) 2026-07-02T07:11:03.000Z

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Other

Additional Information

Environment

• OS: Windows 11 Pro — 25H2 (Build 26200.8737)
• Claude Desktop version: Claude 1.18286.0 (259c3f) 2026-07-02T07:11:03.000Z
• Install type: MSIX (official installer)
• Workspace folder: local NTFS drive (not a network/cloud mount)
• Mode tested: both "Ask before acting" and "Act without asking"

Related Issues

• #46788 — identical symptom on macOS (allow_cowork_file_delete returns

"Permission denied" without showing permission dialog), currently marked stale

• #37814, #24433 — other Cowork permission persistence bugs (different symptom,

same subsystem)