clickwheel 0.11.0

Sync your music library to a classic iPod from a modern Mac

clickwheel

Sync a music library to a classic iPod from a modern Mac — no iTunes required. Scan, clean up metadata, pick what goes on the iPod, and sync, all from the terminal. Optional MCP server lets Claude or other AI clients drive it conversationally.

Install

pipx install clickwheel

Optional extras:

pipx inject clickwheel 'clickwheel[fix]'   # metadata cleanup via beets
pipx inject clickwheel 'clickwheel[mcp]'   # MCP server for Claude / AI clients

Quick Start

Point clickwheel at your music:

mkdir -p ~/.clickwheel
cat > ~/.clickwheel/config.yaml << 'EOF'
music_dir: /path/to/your/music
EOF

Then index it and pick what goes on the iPod:

clickwheel scan      # build the library index
clickwheel select    # interactive checkbox picker
clickwheel sync      # push to the iPod

Commands

Command	Description
clickwheel scan	Index your music library and report on metadata quality
clickwheel fix	Clean up metadata, fetch album art, fill genres via beets
clickwheel select	Interactive picker — checkbox artist selection
clickwheel playlist	List saved playlists or show details for one
clickwheel edit	Add/remove artists or set a description (interactive menus or --add/--remove/--description)
clickwheel heal	Drop playlist references to tracks no longer on disk
clickwheel delete	Delete a saved playlist (with confirmation)
clickwheel diff	Preview what would be added or removed on the iPod
clickwheel sync	Push your playlist to the iPod (with live progress table)
clickwheel sync-plex	Push playlist(s) to your Plex music library (Plexamp picks them up)
clickwheel plex list	List audio playlists on your Plex server (manual vs smart, track counts)
clickwheel plex pull	Recover a Plex playlist into clickwheel's local store (read-back direction)
clickwheel plex doctor	Diagnose Plex configuration — one-shot setup check
clickwheel apple auth	Authorize clickwheel with your Apple Music account (browser-based one-time flow)
clickwheel apple doctor	Diagnose Apple Music configuration — config, .p8, dev token, user token, iCloud Music Library
clickwheel ls	Show what's on the iPod
clickwheel eject	Safely unmount the iPod
clickwheel scrobble	Submit recent iPod listens to Last.fm

Configuration

# ~/.clickwheel/config.yaml
music_dir: /Volumes/Music/Library
ipod_capacity_gb: 64
auto_scan: true

Environment variables (MUSIC_DIR, AUTO_SCAN, etc.) override config values. See docs/configuration.md for the full schema and fix walkthrough.

Optional integrations

Both off by default; opt in only if you use them.

• Last.fm scrobbling — submit iPod listens to Last.fm. See docs/lastfm.md.
• Plex / Plexamp — mirror playlists into a Plex music library so Plexamp picks them up. See docs/plex.md.
• Apple Music — authorize with your Apple Music account; push/pull playlists land in follow-up PRs. See docs/applemusic.md.

MCP server

clickwheel ships an optional MCP server so Claude Code, Claude Desktop, and other MCP-aware clients can drive your library conversationally:

What's on my iPod, and how full is it?

Build me a 45-minute late-night indie folk playlist using only tracks I actually own.

Sync the 'ipod' playlist to my iPod and then eject it.

Quick start with Claude Code:

pipx inject clickwheel 'clickwheel[mcp]'
claude mcp add clickwheel clickwheel-mcp --scope user

The server exposes 33 tools across library, playlist, iPod, Plex, Apple Music, and Last.fm domains, plus a build_playlist prompt with anti-hallucination rules. Destructive operations (delete_playlist, sync_playlist_to_ipod) are gated by client confirmation.

For Claude Desktop config, the full tool reference, and other clients (Cursor, Continue, Cline, Zed), see docs/mcp/.

Requirements

• macOS (iPod sync depends on macOS disk utilities)
• Python 3.11+
• iPod Classic with stock firmware, connected via USB
• FLAC files are excluded from sync (stock firmware limitation)

Contributing

See CONTRIBUTING.md for dev setup, testing, and commit conventions.