2026 — present·cli

clickwheel

A Python library that exposes the iPod sync workflow through two surfaces: a CLI for typed commands and an MCP server so Claude can drive curation conversationally.

Three iPhones side by side in the Claude app using the Clickwheel tool. The first checks what is on the iPod, reporting 487 tracks and 6.3 GB used, led by Taylor Swift with 254. The second builds a road-trip playlist from The Black Keys and stylistically similar artists. The third syncs the finished playlist Highway Howl to the iPod.

Check what's on your iPod, conversationally build a playlist with Claude, and then sync it back all in a single thread.

clickwheel exposes a classic-iPod sync workflow through two surfaces over the same backend. The CLI handles the typed-command path: scan and clean up your library's metadata, interactively pick what goes on the device, preview the diff, and push, all from one terminal session. The MCP server hands those same operations to Claude or other AI clients, so curation can happen in conversation rather than in your head.

A playlist assembled in clickwheel travels to wherever you listen. The iPod sync writes your files directly to stock firmware over USB, no iTunes required. The same playlist pushes to a Plex music library where Plexamp streams those files from your media server, and to Apple Music where catalog matches follow your account anywhere you're signed in. Pull works the other way: a playlist recovered from Plexamp or Apple Music lands back in clickwheel.

Everything plays back into Rewind automatically, so listens on the iPod sit alongside the music streaming through Plexamp and Apple Music.

The MCP server exposes every iPod sync operation as a tool, plus a build_playlist prompt for vibe-based curation with anti-hallucination rules baked in. Tools that write to a destination or delete a playlist are flagged destructive, so MCP clients can gate them behind a confirmation. iTunes did this through a GUI; clickwheel exposes the same operations as composable primitives that the CLI types and the MCP hands to Claude, so curation moves from typing the right command to describing what you want.