[BUG] Claude Desktop (Windows, chat mode): "Always allow" for connector tool delete_emails does not persist; approval prompt reappears every time

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 on Windows, in regular chat mode (not Cowork), the approval prompt "Claude wants to use Delete emails from Yahoo Mail" appears every time the tool is called, even after I select "Always allow" (Ctrl+Shift+Enter).

The choice does not persist. It happens [in every new chat / also within the same chat on a later call: pick one].

When the prompt reappears, the per-tool setting in Settings > Connectors > Yahoo Mail > Delete emails shows [Always allow / Needs approval: fill in].

What Should Happen?

After selecting "Always allow," Claude should call delete_emails for that connector without prompting again, across chats and app restarts.

If delete-type tools are intentionally gated to always require approval regardless of this setting, the "Always allow" option should not be offered for them, or the UI should say so.

Error Messages/Logs

No error is shown. The approval dialog simply reappears.

Steps to Reproduce

1. In Claude Desktop (Windows), connect the Yahoo Mail connector.
2. Start a regular chat (not Cowork) and ask Claude to move an email to Trash, which calls delete_emails.
3. At the prompt "Claude wants to use Delete emails from Yahoo Mail," select "Always allow."
4. Start a new chat and repeat step 2.
5. The same approval prompt appears again.

Claude Model

None

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

Claude 2.7032.0 (6c468a) 2026-09-22T05:53:19.000Z

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Other

Additional Information

Related issues:

• #24433: same symptom in Cowork on macOS. Auto-closed as stale / not planned without a fix. The reporter found approvals were never written back to enabledMcpTools. My case shows the problem also affects regular chat mode on Windows.
• #56954: per-tool "Always allow" settings reset to "Ask" after Desktop auto-updates.

I have a second Yahoo connector ("Yahoo Mail 2") with the same behavior on its delete_emails tool.

Windows build: [winver output]