TrackPort

Get your music onto your offline device.
In three taps.

A focused desktop tool for swim headphones, USB MP3 players, and the other devices that don't stream. Pick the device. Sync your library. Copy. That's it.

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First-install notes

Windows: the installer is currently unsigned, so SmartScreen will pop up the first time you run it. Click "More info" → "Run anyway". (Code signing is on the roadmap once the project has more users.)

macOS: right-click the app the first time and choose "Open" to bypass the Gatekeeper warning. Notarization will land soon.

Linux: AppImage — make it executable (chmod +x) and run.