[BUG] Claude enters plan mode automatically without waiting for user approval

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 Claude determines it should enter plan mode, it immediately enters plan mode without waiting for user confirmation. Even when Claude explicitly asks "Would you like me to enter plan mode?", it doesn't wait for a response before switching.

What Should Happen?

Claude should prompt the user and wait for approval before entering plan mode, allowing the user to decline if they prefer Claude to proceed without planning.

Error Messages/Logs

Example 1 - Statement that should still require approval:

This is a straightforward fix. I should enter plan mode to design this properly.

● Entered plan mode
  Claude is now exploring and designing an implementation approach.

Example 2 - Question that was never answered:

Would you like me to enter plan mode to design a comprehensive reorganization with proper 50+ ID ranges for each category? This will involve:
  1. Defining a new EventId allocation scheme
  2. Updating all EventIds across the logging extension files
  3. Ensuring no overlaps and consistent grouping

● Entered plan mode
  Claude is now exploring and designing an implementation approach.

Steps to Reproduce

1. Start a new Claude Code session
2. Ask Claude to do a complex task that will trigger plan mode prompt
3. Observe that Claude enters plan mode without prompting for approval

Claude Model

Opus

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

2.1.27

Platform

Anthropic API

Operating System

Ubuntu/Debian Linux

Terminal/Shell

PowerShell

Additional Information

_No response_