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.

Full documentation: docs.clickwheel.fm.

Install

pipx install clickwheel

Optional extras:

pipx inject clickwheel 'clickwheel[mcp]'   # MCP server for Claude / AI clients

clickwheel fix (metadata cleanup) runs entirely on the base install, no extras required.

Quick Start

Point clickwheel at your music:

mkdir -p ~/.clickwheel
echo "music_dir: /path/to/your/music" > ~/.clickwheel/config.yaml

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

The iPod workflow:

clickwheel convert transcodes selected FLAC albums to iPod-playable MP3 (interactive picker, or --artist/--album/--all-flac; --bitrate, --force). Output goes to transcode_dir and is indexed into the library, so the resulting MP3s flow through select/sync like any other track. It requires ffmpeg on your PATH (brew install ffmpeg).

Each optional integration has its own doc:

• Plex / Plexamp: push/pull playlists between clickwheel and a Plex music library. See the Plex guide.
• Apple Music: push/pull/delete playlists in your Apple Music account; syncs across Apple devices via iCloud Music Library. See the Apple Music guide.
• Last.fm: submit iPod listens. See the scrobbling guide.

Configuration

# ~/.clickwheel/config.yaml
music_dir: /Volumes/Music/Library
ipod_capacity_gb: 64
auto_scan: true
transcode_dir: ~/.clickwheel/transcoded
transcode_bitrate: 320

• transcode_dir — where clickwheel convert writes converted MP3s (default ~/.clickwheel/transcoded). Kept outside your music library so Plex and the scanner don't pick them up.
• transcode_bitrate — MP3 CBR bitrate in kbps for conversion (default 320).

Environment variables (MUSIC_DIR, AUTO_SCAN, etc.) override config values. See the configuration reference for the full schema and fix walkthrough. Integrations (Plex, Apple Music, Last.fm) are all off by default; opt in via the per-integration guides linked above.

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 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 client setup (Claude Code, Claude Desktop, mobile) and the full tool reference, see the MCP server docs.

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); use clickwheel convert to transcode them to MP3
• ffmpeg on your PATH for clickwheel convert (brew install ffmpeg)

Contributing

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