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If you run Plex, clickwheel can push the same playlists into your Plex music library so Plexamp and Plex web see them alongside your iPod, and pull Plex playlists back into clickwheel. It’s bidirectional.

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Setup

1

Install the Plex extra

2

Configure your server

~/.clickwheel/config.yaml
Keep the token out of YAML, put it in ~/.clickwheel/.env (mode 600) as CLICKWHEEL_PLEX_TOKEN=<your-token>. Treat it like a password. See Plex’s Finding an authentication token if you don’t have it yet.
3

Verify with the doctor

A read-only, five-stage probe: config → connect → music section → sample track → path remap. Each stage that fails tells you exactly what to fix.

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Push and pull

Push reports pushed vs resolved; a gap means Plex hasn’t scanned those files yet, so run a Plex library scan and re-sync. Re-syncing replaces clickwheel’s managed copy but leaves a same-named playlist you made in Plex alone. Pull recovers playlists after a fresh install or Mac wipe. Smart playlists are dynamic queries, so pull skips them unless you pass --include-smart.
clickwheel and Plex can mount the same library at different paths (e.g. clickwheel over SMB, Plex on the NAS’s local filesystem). The remap swaps one prefix for another:
Find Plex’s view at Settings → Manage → Libraries → your music library → Add folders. Leave both empty when Plex runs on the same machine as clickwheel.

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From Claude

You can also drive this from Claude. Set up the MCP server, then the Plex tools are yours.