[BUG] Cross-session send_message shows the approval dialog in bypass/auto permission modes, then fails after clicking Approve

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?

Tool: send_message from the built-in session-management MCP server (ccd_session_mgmt).

When the assistant calls send_message to deliver a message to another local session while the current session is in bypass-permissions or auto mode, the approval dialog still pops up and waits for an explicit click — but after clicking Approve, the tool call fails anyway with This tool requires user approval and is unavailable in unsupervised mode. The dialog's result is collected and then discarded, which is the worst combination: the user is interrupted for a confirmation that cannot succeed. The same call works fine in default permission mode (dialog → approve → message delivered to the target session).

The unsupervised-mode guard itself makes sense as protection against unattended cross-session injection, but it appears to run independently of (and after) the confirmation dialog rather than trusting it — even though the dialog demonstrably renders and blocks on a real human click in bypass mode.

What Should Happen?

Either (preferably) honour the explicit approval (the click is the supervision the guard wants), or (at least) check the permission mode before raising the dialog and fail fast without prompting.

Error Messages/Logs

Steps to Reproduce

Two local sessions; in session A set bypass-permissions (or auto) mode; ask the assistant to send a message to session B via send_message; click Approve on the dialog → error. Switch session A to default mode and repeat → succeeds.

Claude Model

Not sure / Multiple models

Is this a regression?

I don't know

Last Working Version

_No response_

Claude Code Version

Claude Code 2.1.169 (desktop), macOS (Darwin 25.5.0)

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Other

Additional Information

_No response_