Putting Music on an iPod Shuffle
Sync songs, audiobooks, playlists and podcasts to any iPod shuffle from a Mac without iTunes, fill it automatically, and get its play counts back.
The iPod shuffle has no screen, so everything about it is chosen on your Mac. Here's how to fill one with ClassicTunes, on any Mac from macOS 12 Monterey on.
Experimental: ClassicTunes supports every iPod shuffle, 1st to 4th generation, but hasn't been tested on a real one yet. Take a snapshot before the first sync (ClassicTunes offers one), so the shuffle can be put back exactly as it was.
Connect it
- 1st generation (the stick): plug it straight into a USB port, or a USB-C adapter.
- 2nd generation (the clip): sit it in its dock, which plugs into USB.
- 3rd and 4th generation: use the short cable that goes into the headphone socket.
It appears in ClassicTunes' sidebar under iPods, named and identified by model. See Connecting an iPod.
Choose what goes on
A shuffle holds between 512 MB and 4 GB, so it's rarely your whole library. On the shuffle's page:
- choose the artists, albums, genres or playlists to sync, and
- turn on Fill free space to top it up with more (as iTunes' Autofill did): songs you haven't heard, your highest rated, most played, recently added, or random albums.
See Syncing an iPod. Preview Sync shows what will go on, and how much space is left, before anything changes.
What a shuffle gets
| 1st and 2nd generation | 3rd and 4th generation | |
|---|---|---|
| Songs and audiobooks | Yes | Yes |
| Playlists (for VoiceOver's playlist menu) | — | Yes |
| Podcasts | — | Yes |
| Play counts back to your library | Yes | Yes |
- Songs play in the order of your library with shuffle off, and in a random order with it on. Songs marked Skip when shuffling in Get Info, and audiobooks, are left out of shuffle; audiobooks remember their place.
- FLAC, Ogg and other formats are converted to AAC as they're copied, and so is Apple Lossless, which shuffles don't play. See Tidying up for songs no iPod can play.
- ClassicTunes doesn't make the spoken song titles VoiceOver reads on the 3rd and 4th generation, so VoiceOver is off; the playlist menu still works.
- Photos, videos and album art don't go on a shuffle.
Plays come back
The shuffle counts how many times each song was played. At the next sync, those plays join your library's play counts, and with scrobbling on, they're sent to Last.fm or ListenBrainz. A shuffle doesn't record when each play happened, so they're dated at the sync; Last.fm only takes plays from the last 14 days.
Finder or ClassicTunes?
Finder can sync a shuffle from the Music app too. ClassicTunes works without the Music app, converts formats the shuffle can't play, fills it for you, and shows each change first. See Syncing an iPod on a Mac in 2026 for every option.