[BUG] - Claude Code in Cursor implements in edit automatically mode even though Plan mode is turned on

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?

I switched to plan mode in Cursor, and instead of operating in plan mode, CC just proceeded in edit automatically mode. I had it diagnose itself. Here is what it reported: Most likely cause: when I called ExitPlanMode after you approved the first plan, Claude Code automatically exits plan mode. To go back into it, you have to actively re-enter (Shift+Tab cycles modes in the CLI; in the VSCode extension it's the mode selector near the input). If you toggled it but focus was elsewhere, or if it was toggled after the message was already submitted, the message would ship in normal mode with no plan-mode system-reminder attached — which is exactly what I saw on that turn (no reminder, so I proceeded).

Two quick ways to verify before your next "plan this" message:

Look at the mode indicator in Claude Code (status strip at the bottom of the terminal or the VSCode chat panel) — it shows "plan mode" in orange when active.
Send a test message like "what mode are you in?" — I'll confirm from the system reminders I'm receiving.
If the indicator says plan mode is on but my response shows I'm executing anyway, that'd be a Claude Code bug worth reporting at https://github.com/anthropics/claude-code/issues.

I'll report it, because the plan indicator was definitely toggled on
Helpful details to include in the report so they can repro:

Environment: Claude Code VSCode extension on Windows 11 (since that's your setup).
Repro sequence: enter plan mode → approve a plan via ExitPlanMode → wait for implementation to finish → send next message while the mode indicator still shows plan mode on → message arrives without the plan-mode system-reminder.
Expected: system-reminder should be attached to every user message while the indicator shows plan mode.
Hypothesis worth calling out: the issue may be tied to the automatic mode flip that fires when ExitPlanMode is called — if the indicator state and the backend state drift out of sync after that, the UI shows plan mode on but the message is sent in normal mode.
Session timestamp: today, 2026-04-24, around the time of commit 4a644ac4.
If you can grab a screenshot of the indicator showing "plan mode" while the conversation turn that got executed is visible, that's gold for the repro.

<img width="1464" height="1157" alt="Image" src="https://github.com/user-attachments/assets/43df1447-a6ae-4c0f-876f-7167b6e19235" />

What Should Happen?

See problem description - self explanatory.

Error Messages/Logs

Steps to Reproduce

In cursor:

• Do something in plan mode, let it exit plan mode and go back to edit automatically
• Switch back to plan mode
• Give it some instruction
• Watch it stay stuck in edit automatically even though you have plan mode toggled on

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

2.1.112 (Claude Code)

Platform

Other

Operating System

Windows

Terminal/Shell

WSL (Windows Subsystem for Linux)

Additional Information

_No response_