[BUG] Bug: settings.json permission path matching is case-sensitive on Windows

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?

Description

On Windows (NTFS), path matching in settings.json permissions is case-sensitive,
even though Windows itself is case-insensitive. A permission written as
C:\\work\\ai\\XX\\src\\** silently fails to match C:\Work\ai\XX\src\ —
causing unexpected permission prompts with no diagnostic message explaining the mismatch.

Steps to Reproduce

1. Open a project in C:\Work\ai\XX (note capital W)
2. Add this to .claude/settings.json:

"Write(C:\\work\\ai\\XX\\src\\**)" ← lowercase 'work'

1. Ask Claude to edit a file in src\
2. Permission prompt fires despite the rule existing

Fix: Change to "Write(C:\\Work\\ai\\XX\\src\\**)" (matching exact disk casing) → prompts stop.

Expected Behavior

Path matching should be case-insensitive on Windows, consistent with how NTFS
and Windows path APIs work. Either casing should match.

Actual Behavior

Only exact-case string match works. No warning or diagnostic when a rule silently fails to match.

Environment

• OS: Windows 11
• Claude Code: VS Code extension

What Should Happen?

Path matching should be case-insensitive on Windows, consistent with how NTFS
and Windows path APIs work. Either casing should match.

Error Messages/Logs

Steps to Reproduce

Steps to Reproduce

1. Open a project in C:\Work\ai\XX (note capital W)
2. Add this to .claude/settings.json:

"Write(C:\\work\\ai\\XX\\src\\**)" ← lowercase 'work'

1. Ask Claude to edit a file in src\
2. Permission prompt fires despite the rule existing

Claude Model

Opus

Is this a regression?

No, this never worked

Last Working Version

_No response_

Claude Code Version

2.1.85

Platform

Anthropic API

Operating System

Windows

Terminal/Shell

Windows Terminal

Additional Information

Regarding Terminal, it was from withing Claude desktop on Windows (ARM64) and is best described by Claude itself.

from the Claude desktop app's built-in Bash tool, which appears to run in its own shell environment (not directly in PowerShell or CMD — it's an internal subprocess). The terminal type in the issue form is really asking where Claude Code runs, which is the desktop app — so "Other: Claude desktop app (Windows)" is still the right answer.