Documentation
Everything you need to know to get your music onto your iPod.
ThirtyPin is a native macOS app for syncing music to classic iPods. It connects directly to your iPod over USB and reads from any folder of music files on your Mac — no iTunes, no Music.app, no Apple ID required.
It is named after the 30-pin dock connector used on iPods from the original 2001 model through the iPod Classic 7th generation — the connector that defined a decade of portable music.
Open ThirtyPin and follow the three-step welcome guide:
None in particular. ThirtyPin walks the entire folder tree you point it at and finds all audio files, regardless of how they are organized. Artist/album subfolders are common but not required.
Metadata (title, artist, album, track number) is read from the files themselves, so well-tagged files produce the best results.
ThirtyPin can read any audio format that macOS supports for metadata. For syncing to your iPod:
ThirtyPin looks for album art in two places, in order of preference:
cover.jpg, folder.jpg, artwork.jpg, or similar in the same folder as the tracksArtwork is scaled to the maximum dimension your iPod supports before being written to the device.
Before ThirtyPin moves any files, it builds a complete plan showing exactly what will happen: which tracks will be added, which will be updated, and which will be removed. You can review this plan in full before committing.
The plan also shows a storage estimate — how many bytes will be added or freed — and warns you if the selection won’t fit on your device.
Safe (default): ThirtyPin only removes tracks it previously added. Tracks synced by iTunes, Music.app, or any other tool are left alone. This is the recommended mode.
Full Replace: ThirtyPin treats the entire iPod as its own library and removes anything not in your current selection. Use this if you want ThirtyPin to be the sole manager of your device.
Yes. ThirtyPin supports two selection modes:
In Safe mode, no. ThirtyPin tracks exactly which tracks it has synced. It will only remove tracks it previously added, and only if they are no longer in your selection. Music synced by iTunes or Music.app is never touched.
In Full Replace mode, yes — tracks not in your current selection will be removed, regardless of their origin. You will see a full list of planned removals in the sync preview before anything happens.
Transcoding is the process of converting an audio file from one format to another. ThirtyPin transcodes files when:
ThirtyPin uses FFmpeg to handle transcoding. You can configure the target format (AAC or MP3) and bitrate in Settings.
Yes. By default, ThirtyPin keeps converted files in a cache so they don’t need to be re-encoded on subsequent syncs. You can disable this in Settings if you’d prefer to save disk space.
The cache is keyed on the source file’s fingerprint and your transcoding settings, so changing bitrate or format will trigger a fresh transcode.
ThirtyPin can use either a bundled FFmpeg binary or a system-installed one. If you install FFmpeg via Homebrew (brew install ffmpeg), ThirtyPin will find it automatically. A bundled copy may be included in future releases to remove this dependency.
Artwork is supported on:
The original 1G–4G monochrome iPods, iPod mini, and iPod Shuffle do not have screens capable of displaying artwork.
ThirtyPin handles resizing automatically. Most classic iPods support artwork up to 320×320 pixels. ThirtyPin scales artwork down to the maximum your specific model supports before writing it to the device.
For best results, use square images of at least 300×300 pixels embedded directly in your audio files.
Yes, in Safe mode. ThirtyPin records every track it adds and only removes those it added. Tracks synced by iTunes or Music.app are treated as “unmanaged” and are never touched automatically.
However, we recommend not running ThirtyPin and iTunes/Music.app concurrently on the same iPod, as both writing to the iPod database at the same time could cause issues.
ThirtyPin stores all its data in a single SQLite database at:
~/Library/Application Support/ThirtyPin/thirtypin.sqlite
This database contains your settings, per-device sync selections, track records (the source↔device mapping), and the conversion cache. Your music files are never modified.
Yes. ThirtyPin maintains a completely separate sync selection and track record for each iPod, identified by the device’s unique ID. Connect multiple iPods (one at a time) and ThirtyPin will keep their states separate.
ThirtyPin’s pricing model is still being determined. The project is open source and the initial release will be available at no cost. Check the changelog and sign up for the launch notification for updates.
No. ThirtyPin works entirely offline. Your music stays on your Mac and your iPod. No data is sent anywhere.
No. ThirtyPin is specifically designed for classic iPods — the ones that use the 30-pin connector or are based on the same iPod database format. iPod Touch and iPhone use a completely different protocol managed by Apple.
Try the following:
If problems persist, report a bug with details about your iPod model and macOS version.
ThirtyPin is open source. The project is hosted on GitHub. Contributions, bug reports, and feature suggestions are welcome — head to the GitHub repository to get involved.