sortwise

AI-powered file organizer for macOS. Uses Claude to understand what your files actually are — not just their extensions — and sorts them into intuitive categories like receipts, travel, work, photos, etc.

Comes with a native macOS menu bar app and a disk usage monitor.

How it works

1. Scans your folders for files (Downloads, Documents, Desktop — configurable)
2. Sends only the filenames to Claude Haiku for classification (~$0.001 per run)
3. Moves files into category subfolders (e.g. ~/Downloads/receipts/, ~/Downloads/travel/)
4. Archives anything older than 30 days into _old/{category}/

The AI understands context from filenames:

File	Extension-based	AI-powered
Delta_FlightTicket_AB12CD.pdf	documents	travel
Receipt-2998-0321-9220.pdf	documents	receipts
Q3_Marketing_Strategy.pdf	documents	work
IMG_5341.PNG	images	photos
dreaming-outloud-pro-regular.zip	archives	design
vacation-budget-2026.xlsx	documents	personal

Requirements

• macOS 12+
• Python 3.10+ (python3 --version to check)
• pipx (brew install pipx if not installed)
• Xcode Command Line Tools for the menu bar app (xcode-select --install)
• Claude API key from console.anthropic.com (optional — works without AI too)

Install

Quick start

git clone https://github.com/fabioderiu/sortwise.git
cd sortwise
make app

This installs both the CLI and the native menu bar app to /Applications.

CLI only

# From the repo
git clone https://github.com/fabioderiu/sortwise.git
cd sortwise
make install

# Or directly with pipx
pipx install git+https://github.com/fabioderiu/sortwise.git

Setup your API key

sortwise --setup-key
# Paste your key when prompted

Or set it as an environment variable:

export ANTHROPIC_API_KEY=sk-ant-...

No API key? The tool works without one — use --no-ai for free extension-based sorting.

Usage

CLI

# Preview what it would do (dry-run, default)
sortwise

# Actually move files
sortwise --move

# Organize a specific folder
sortwise --dir Documents

# Use extension-based sorting (free, no API key)
sortwise --no-ai

# Change age threshold for archiving
sortwise --move --age-days 14

# Enable/disable folders for auto-tidy
sortwise --enable Documents
sortwise --enable Desktop
sortwise --disable Desktop

Menu bar app

After make app, open Sortwise from Applications or Spotlight. A native icon appears in your menu bar:

• Tidy Now — organize all enabled folders immediately
• Preview — dry-run via macOS notification
• Disk Usage — see your largest folders and files, click any to reveal in Finder
• Watched Folders — toggle Downloads, Documents, Desktop
• Auto-tidy — runs every 4 hours when enabled
• AI Classification — toggle between AI and extension-based sorting

Launch at login

System Settings → General → Login Items → add Sortwise.

Uninstall the app

make app-uninstall

Headless auto-tidy (launchd)

If you prefer the CLI running on a schedule without the menu bar app:

make launchd-install    # every 4 hours
make launchd-uninstall  # remove

Example output

  🧹 sortwise v0.1.0

  Classifying with AI sorting...
  Watching: ~/Downloads, ~/Documents

  📂 ~/Downloads (95 items)
  [DRY RUN] 95 files to organize:

  📁 receipts/
     ↳ Receipt-2998-0321-9220.pdf
     ↳ Transaction-Mar-2026.pdf
  📁 travel/
     ↳ Delta_FlightTicket_AB12CD.pdf
     ↳ Airbnb_Confirmation_Tokyo.pdf
  📁 work/
     ↳ Q3_Marketing_Strategy.pdf
     ↳ Sales_Report_2026.pdf
  📁 photos/
     ↳ IMG_5341.PNG
     ↳ IMG_5342.PNG
  📁 _old/archives/
     ↳ old-project-backup.zip

  📂 ~/Documents (14 items)
  Already tidy!

  Run with --move to execute.

How much does it cost?

Each run sends only filenames (not file contents) to Claude Haiku. A typical run with ~100 files costs less than $0.001. Running every 4 hours, that's about $0.07/month.

Use --no-ai for completely free extension-based sorting.

Configuration

Config is stored at ~/.config/sortwise/config.json:

{
  "api_key": "sk-ant-...",
  "watched_dirs": {
    "Downloads": true,
    "Documents": false,
    "Desktop": false
  },
  "use_ai": true,
  "auto_enabled": true,
  "auto_interval_minutes": 240
}

How is this different from Hazel / other tools?

	sortwise	Hazel	Built-in Stacks
AI classification	Understands file purpose from name	Rule-based only	Extension only
Cost	~$0.07/month (or free with --no-ai)	$42 one-time	Free
Open source	Yes (MIT)	No	No
Menu bar app	Native Swift, ~40 MB RAM	Yes	N/A
Disk usage monitor	Built-in	No	No
Multi-folder	Downloads, Documents, Desktop	Any folder	Desktop only
Dry-run mode	Default behavior	No	No

Uninstall

cd sortwise
make uninstall        # remove CLI
make app-uninstall    # remove menu bar app
make launchd-uninstall # remove auto-tidy schedule

Config is stored at ~/.config/sortwise/ — delete it to remove all settings.

License

MIT