[BUG] Write tool gate denies path that permissions.allow glob clearly matches

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?

Environment: macOS Darwin 25.5.0, Claude Code Opus 4.7

Settings (~/.claude/settings.json, relevant excerpt):
"permissions": {
"allow": [
"Write(/Users/mark.orsted/obsidian/10-Projects/**)",
"Bash(python3 -c *)"
],
"additionalDirectories": ["/Users/mark.orsted/obsidian"]
}

Hypothesis: Write tool gate uses a different (broken) evaluator than Bash, OR a per-file permission cache that misses after resume and falls through to a UI prompt regardless of glob match.

Workaround: Route writes through Bash(python3 -c "open(p,'w').write(...)") when this happens.

What Should Happen?

Expected: Write succeeds first try because the path matches the ** glob.

Actual: Three permission denials, then a workaround via Bash succeeds for the same path.

Error Messages/Logs

Steps to Reproduce

Repro:

1. Attempt Write to /Users/mark.orsted/obsidian/10-Projects/<Proj>/Sessions/<new-file>.md
2. Tool returns: "Claude requested permissions to write to <path>, but you haven't granted it yet."
3. Retry 2x — same denial.
4. Bash invocation python3 -c "open('<same path>','w').write(...)" — succeeds first try.
5. After SessionStart:resume, Write to a different new file in the same dir works without prompt.

Expected: Write succeeds first try because the path matches the ** glob.
Actual: Three permission denials, then a workaround via Bash succeeds for the same path.
Hypothesis: Write tool gate uses a different (broken) evaluator than Bash, OR a per-file permission cache that misses after resume and falls through to a UI prompt regardless of glob match.
Workaround: Route writes through Bash(python3 -c "open(p,'w').write(...)") when this happens.

Claude Model

None

Is this a regression?

Yes, this worked in a previous version

Last Working Version

_No response_

Claude Code Version

2.1.150.

Platform

Anthropic API

Operating System

macOS

Terminal/Shell

Terminal.app (macOS)

Additional Information

_No response_