[BUG] `"showClearContextOnPlanAccept": true` not working as a global setting for new projects started in v2.1.100

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?

Ever since v2.1.81 "showClearContextOnPlanAccept": true has been very essential for getting predictable behavior out of Claude Code. Previously, setting it as a global setting in ~/.claude/settings.json applied it to all local instances

I started a new project today under v2.1.100, and the global setting is not affecting local. To be clear, ./.claude/settings.local.json does not have "showClearContextOnPlanAccept" field, so the expected behavior is to pull from global settings. Other projects created before v2.1.100 do this successfully

What Should Happen?

Global settings should be global

Error Messages/Logs

Steps to Reproduce

1. enable "showClearContextOnPlanAccept": true globally in ~/.claude/settings.json
2. start a new project by going to a project directory and running 'claude' in terminal
3. make a plan in planning mode
4. fail to see Yes, clear context (<#>% used) and auto-accept edits

Claude Model

Sonnet (default)

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

v2.1.100

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

_No response_