[Bug] Windows path length limit causes file deletion failures and token loss

**Bug Description**
Windows path length limit causing file deletion failures and token loss

I am experiencing recurring file deletion errors on Windows because the generated file paths exceed the OS maximum character limit.

For example, the heavily nested directory structure creates excessively long paths like this:
C:/Users/jacqu/AppData/Local/Temp/claude/C--repo-agentic-sdlc-factory/a06aa50d-2fb3-418b-a966-f6928bc4fc88/scratchpad...

Because the system fails to handle or delete these deeply nested files properly, it has caused my workflow to fail repeatedly, resulting in a significant loss of wasted tokens. Please consider flattening the temporary directory structure or implementing a robust workaround for Windows long path limitations to prevent this.

**Environment Info**
- Platform: win32
- Terminal: windows-terminal
- Version: 2.1.274
- Feedback ID: ac6cab76-035c-42ee-91a6-9de78f1442c5

**Errors**
```json
[]
```

No source file or test is named. Start by reproducing the deeply nested temporary path on win32 and tracing the file-deletion failure; compare the temporary directory structure with the reported path-length limit. Done means temporary files are deleted reliably on Windows without the described workflow or token loss.

Written by the indexing model from the issue text.