The image at that path can't be transcribed due to two issues: 1. **Unrecognized file format**: The Read tool detected the file header as `c0 3b 39 98 00 00 00 01`, which doesn't match JPEG, PNG, GIF, or WebP. This could be a TIFF, JPEG 2000, or a corrupted/failed download. 2. **Security sandbox**: Bash commands are restricted to the working directory (`/Users/jheppler/work/chnm/sustainability/pwd`), so I can't inspect or copy the file from `/var/folders/…`. The root problem is in `transcribe.py`: it downloads images to `tempfile.TemporaryDirectory()` (under `/var/folders/…` on macOS) and passes those paths to `claude -p`. But Claude Code's `--allowedTools Read` security model only permits reads within the working directory, so I can never reach files in the system temp dir. **Fix**: change `transcribe.py` to write the temp directory inside the project tree instead of the system temp: ```python # Instead of: with tempfile.TemporaryDirectory(prefix="pwd_transcribe_") as tmpdir: # Use a subdir of the project: tmpdir = SCRIPT_DIR / ".tmp_images" tmpdir.mkdir(exist_ok=True) try: # ... existing code ... finally: shutil.rmtree(tmpdir, ignore_errors=True) ``` Or more surgically, pass `dir=SCRIPT_DIR` to `TemporaryDirectory`: ```python with tempfile.TemporaryDirectory(prefix="pwd_transcribe_", dir=SCRIPT_DIR) as tmpdir: ``` That puts the temp dir at `_transcription/pwd_transcribe_XXXX/` which is inside the allowed working tree, and the Read tool will be able to load the image files.