`chromeEnabled: true` in settings doesn't reliably enable CiC — `claude --chrome` flag does

Summary

claude --chrome works to connect Claude-in-Chrome. Running claude with chromeEnabled: true in settings.json does not always connect CiC. They should be equivalent but aren't. No error message explains the difference.

Steps to Reproduce

1. Set "chromeEnabled": true in ~/.claude/settings.json and/or ~/.claude/settings.local.json
2. Run claude (without --chrome flag)
3. CiC tools are listed but don't reliably connect to Chrome

vs.

1. Run claude --chrome
2. CiC tools connect and work

Extra Context

This is especially painful when using two different machines with the same project directory via cloud storage (e.g., Google Drive). The settings file syncs across machines, but CiC behavior is inconsistent. The flag works, the setting doesn't. No error tells you why.

Expected Behavior

chromeEnabled: true in settings should behave identically to claude --chrome.

Environment

• macOS (Darwin 24.6.0)
• Claude Code CLI
• Chrome with Claude-in-Chrome extension installed