A weekly automation that tidies your Documents, Desktop and Downloads folders, and never deletes anything on its own.
It routes loose files into project folders, groups screenshots into monthly folders, and flags anything suspicious, like installers and unknown folders, for you to review rather than touching it itself.
Before you start
You need two things:
- Claude with Cowork mode for file access and a sandbox to run Python, plus the Scheduled Tasks feature.
- 10 minutes to review the dry run output before you let it apply changes.
1. Write the organizer script
Paste this into Claude:
Write me a Python script called organize_files.py that tidies up my ~/Documents, ~/Desktop, and ~/Downloads folders. Requirements:
- Scan all three folders for loose files sitting at the top level (not already inside a project folder)
- Match filenames against patterns I define (e.g. anything with "invoice" or "receipt" goes to a Finance folder, screenshots go to Desktop/Screenshots) — let me tell you my actual project names and folder mappings before you finalize the rules
- Never touch active code projects — skip any folder containing .git, package.json, Cargo.toml, pyproject.toml, or similar markers
- Move unmatched loose files into a catch-all ~/Documents/_Inbox folder
- Group screenshots already in Desktop/Screenshots into YYYY-MM monthly subfolders based on file date
- Flag but never delete: installers (.dmg, .pkg, .exe, .msi), and unrecognized folders in Downloads — list them in the report only
- Support a --apply flag; default to dry-run (print what it would do without moving anything)
- Write a timestamped text report and a JSON log each run
- Save the script to ~/Documents/_Tools/organize_files.py
Ask me about my specific project folders and naming conventions before writing the rules.Answer Claude’s follow-up questions about your actual folder names, then let it write the script.
2. Test it in dry run mode
Paste this:
Run ~/Documents/_Tools/organize_files.py in dry-run mode (no --apply) and show me the full report.Check that files are routed where you expect, that nothing sensitive gets silently moved, and that your active project folders are left alone. If something is off, tell Claude what to fix and re-run until the dry run report looks right. Only then run it once with --apply to confirm a real pass works.
3. Schedule it to run weekly
Paste this:
Set up a scheduled task that runs my file organizer weekly. It should:
1. Run every Sunday evening
2. Request access to ~/Documents, ~/Desktop, and ~/Downloads if not already mounted, and request delete permission for all three (moving files requires it)
3. Run ~/Documents/_Tools/organize_files.py in --apply mode, writing a timestamped report and JSON log to ~/Documents/_Organizer_Logs/
4. Post a short summary in chat: how many files were moved and where, how many screenshots were regrouped, and any flagged items (installers, unknown folders) that need my manual review
5. Never delete flagged items automatically — leave them for me to decide on, and just list them
6. Keep the summary under 200 words — this is routine maintenance, no need to be chatty
End by telling me the log file path for the full record.4. Review flagged items each week
Each run’s summary calls out anything it did not touch: old installers, unrecognized folders in Downloads, and the like. Skim these and decide manually whether to keep, move, or delete them. The full report and JSON log are kept in _Organizer_Logs if you need the details later.