Documentation

How to use every part of ClassicTunes, from adding your first album to scripting a sync.

Getting Started

  • Getting StartedInstall ClassicTunes, add your music, connect your iPod and run your first sync, checking it first with Preview Sync.
  • Trial and LicenseThe 14-day free trial, buying a license, activating it on up to two Macs, and moving it to a new Mac.

Guides

  • Syncing an iPod on a Mac in 2026Every way to get music onto an iPod classic, nano or mini from a modern Mac, from Finder to ClassicTunes and the other apps, and which to choose.
  • When Finder Won't Sync Your iPodWhat to try when a classic iPod doesn't appear in Finder on your Mac, won't sync, is missing songs, or asks to be restored, and another way to sync it.
  • Apple Music Songs and Your iPodWhy songs from an Apple Music subscription can't go on a classic iPod, how to tell them apart, and the ways to get music you can sync.
  • Copying Music Off an iPodGet the songs, playlists, play counts and covers on an old iPod back onto your Mac, without changing anything on the iPod.

Your Library

  • Your LibraryAdd music from files, folders and the Music app, browse it by album, artist or song, edit song details with Get Info, and remove what you don't want.
  • ArtworkWhere album covers come from, how to choose your own, find missing covers online, replace small covers with larger ones, and how artwork reaches your iPod.
  • Tidying Up Your LibraryFix album details from Apple and MusicBrainz, merge duplicates and split albums, label discs, find stray files and songs iPods can't play.
  • Importing CDsImport CDs with details and covers from MusicBrainz, check every track against AccurateRip, play a CD without importing, and re-import damaged songs.
  • Several LibrariesKeep separate libraries for different people or iPods, switch between them, and move a library to another folder or drive.
  • Metadata BackupsSave your songs' details, play counts, ratings and artwork to a file, restore them later, and use the backups made before every big change.

Playback

  • Playing MusicPlay songs, videos, podcasts and audiobooks on your Mac, with Up Next, shuffle and repeat, the equalizer, AirPlay and the Play key.
  • PlaylistsMake playlists and smart playlists, add and arrange songs, import and export .m3u playlists, and keep On-The-Go playlists made on the iPod.
  • Listening HistorySee every song you've played to the end in ClassicTunes, with when you played it, and play, search, sort and tidy the list.
  • PodcastsSubscribe to podcasts by searching or pasting a feed, download and play episodes, sync them to an iPod, and import or export OPML.
  • AudiobooksListen to audiobooks with chapters, your place kept and your choice of speed, combine files into one book, and sync them to an iPod.
  • VideosAdd movies, TV shows, music videos and home videos, play them on your Mac, set each one's kind, and sync them to an iPod in a format it plays.
  • PhotosImport photos from cards, cameras and folders, browse the Photos app's library, and choose the photos and videos each iPod gets.
  • Scrobbling to ListenBrainzSend what you play on your Mac, your iPod and Rockbox to ListenBrainz, including what's playing now, with plays kept while offline.

iPods

  • Connecting an iPodPlug in an iPod, read its page, choose which library it belongs to, and rename, eject or forget it.
  • Syncing an iPodChoose what goes on each iPod, sync it, fill its free space, and understand what a sync changes, keeps and reads back.
  • Preview SyncSee exactly what a sync will add, convert, remove and change on your iPod, and how much space is left, before anything on it changes.
  • SnapshotsSave a complete copy of your iPod, get offered one before risky syncs, and restore the iPod to exactly how it was.
  • iPod toolsRockbox support, click wheel and Rockbox games, importing from an iPod, diagnostics, and the other tools on an iPod's page.
  • Supported iPodsEvery iPod model and how well ClassicTunes supports it, from the original iPod to the iPod nano 7th generation, with what each one can sync.

Music Players

  • Music playersSync your library to music players that aren't iPods, such as the Shanling Q2, Innioasis Y1, Tangara, FiiO Echo Nano, a Rockbox player or any SD card.

Automation

  • AppleScriptScript ClassicTunes with AppleScript, with example scripts and a complete reference to its dictionary of classes, properties, commands and enumerations.
  • ShortcutsEvery ClassicTunes action in the Shortcuts app, what each one takes and gives back, and the items you can pick from.

Reference

  • SettingsEvery tab and setting in ClassicTunes' Settings window, what each one does, and which ones belong to each library.
  • Keyboard shortcutsEvery keyboard shortcut in ClassicTunes, grouped by menu, plus the keys that work in album grids, photos, Get Info and the player.
  • UpdatesHow ClassicTunes checks for and installs new versions, how to check by hand, and why an update never interrupts a sync.
  • Privacy and safetyWhat stays on your Mac, exactly what ClassicTunes sends over the internet and when, and the safeguards that protect your iPod and your library.

Help

  • TroubleshootingWhat to do when an iPod doesn't appear, gets ejected, won't sync or eject, when songs are missing from the iPod, and other common problems.
  • FAQAnswers to common questions about ClassicTunes, from which Macs and iPods it works with to what happens to the music already on your iPod.