[BUG] CoWork "Always allow" does not persist within same prompt — repeated permission prompts for each file edit

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 CoWork in Claude Desktop, clicking "Always allow" for file edit permissions does not persist — even within the same prompt response. If Claude edits the same file 5 times during a single response, the permission dialog appears 5 times.

This is distinct from the known cross-session persistence bugs (#24433, #7472, #22576). This is a regression where permissions do not persist within a single agentic response, making CoWork unusable for any multi-edit task.

Issue started Thursday March 19, coinciding with version 1.1.7714 release.

What Should Happen?

Clicking "Always allow" should persist at minimum for the duration of the current response. The user should not be prompted repeatedly for the same file within a single Claude response.

Error Messages/Logs

No error messages — the permission dialog simply reappears for each file edit operation, even after clicking "Always allow"

Steps to Reproduce

Start a new CoWork session in Claude Desktop 1.1.7714
Ask Claude to perform a task that requires multiple edits to the same file (e.g., "refactor this function and update the tests")
When the "Claude wants to use Updating file" dialog appears, click "Always allow" (⌘⏎)
Observe that Claude prompts for permission again for the next edit to the same file, within the same response

Claude Model

Opus

Is this a regression?

Yes, this worked in a previous version

Last Working Version

Version prior to 1.1.7714 (before March 19, 2026)

Claude Code Version

1.1.7714 (3bd6f6) 2026-03-19T14:50:53.000Z

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

This is a critical regression affecting CoWork usability. Affected: file edits. Not affected: file reads.

Related issues: #24433, #7472, #22576, #30953 — but this bug is more severe as it affects persistence within a single prompt, not just across sessions.

Deploying CoWork across an enterprise team; this regression blocks productive use.