[BUG] --dangerously-skip-permissions: Plan mode only works on first invocation, subsequent uses skip planning and execute directly

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 running Claude Code with --dangerously-skip-permissions, plan mode (toggled via /plan) only activates correctly on the first use within a session. From the second invocation onward, plan mode is completely ignored — Claude Code skips the planning phase and directly executes actions.

What Should Happen?

Plan mode should activate consistently every time it is toggled on via /plan, regardless of how many times it has been used during the session. Claude Code should always present a plan for review before executing when plan mode is active.

Error Messages/Logs

No error messages displayed. The issue is behavioral — plan mode silently fails
to activate after the first use, with no warnings or errors in the output.

Steps to Reproduce

1. Launch Claude Code with claude --dangerously-skip-permissions
2. Toggle plan mode on via /plan
3. Submit a prompt — Claude correctly enters plan mode and presents a plan ✅
4. Toggle plan mode off, then toggle it back on via /plan
5. Submit another prompt — Claude skips planning and executes directly ❌

Claude Model

Opus

Is this a regression?

Yes, this worked in a previous version

Last Working Version

2.1.75

Claude Code Version

2.1.91

Platform

Anthropic API

Operating System

Other Linux

Terminal/Shell

Xterm

Additional Information

This issue is 100% reproducible. The first /plan toggle in a session always works as expected, but every subsequent toggle fails silently. Restarting Claude Code resets the behavior (i.e., the first /plan works again, but the second does not).