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.

The Claude desktop app showing clickwheel's get_ipod_contents tool call. Claude reports 428 tracks across 7 artists, led by Taylor Swift, Sabrina Carpenter, The Black Keys, Weezer, Olivia Rodrigo, Bob Dylan, and The Rolling Stones, with 5.9 GB used of 59.4 GB.
The same Claude conversation, continued. Claude inventories grunge in the library, listing Nirvana, Pearl Jam, Soundgarden, Alice in Chains, and Stone Temple Pilots as the essentials, with The Smashing Pumpkins flagged as grunge-adjacent.
The final step of the clickwheel chat. Claude proposes Blind Melon's self-titled record, lands on a 43-track, three-hour playlist called Upper Left, and the sync_playlist_to_ipod tool kicks off a sync at 19 of 47 tracks.

The iPod reads back as a profile. Mostly Taylor Swift, a long tail of other artists, and most of the device still unfilled.

Curation goes conversational. Claude reads the library and the iPod, so a vague request for grunge produces specific, justified picks.

The conversation produces a playlist. Upper Left, 43 tracks of Pacific Northwest grunge, on its way to an iPod over USB.

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.

Links

Mentioned in

More projects