Features

Everything ClassicTunes does, with a link to the full documentation for each.

Your iPod

Sync music, podcasts, audiobooks, videos and photos: your whole library, or chosen artists, albums, genres and playlists.
Preview Sync shows what a sync will add, convert and remove before anything on the iPod changes.
Fill the free space with unplayed songs, your highest rated or most played, recently added songs or random albums.
Songs in formats an iPod can't play (FLAC, Ogg, Opus and more) are converted as they're copied.
Plays, ratings and where you left off in audiobooks and podcasts come back from the iPod at each sync, and On-The-Go playlists join your library.
Smart playlists go on the iPod with their rules, so it keeps them up to date itself.
Snapshots of the whole iPod, offered before a first sync or one that removes a lot, and restored in one step.
Import everything on an iPod into your library, with its playlists, covers and play counts.
iPod Diagnostics, click wheel games kept safe, and Rockbox support: playlists, play logs and games.
Almost any MP3 or portable music player can be synced too: anything that shows up on your Mac as a drive or takes an SD card, from Rockbox players to FiiO, Shanling and Innioasis.

Add music and videos by dragging them in, with a review window that shows what will be added and fills in missing details from Apple and MusicBrainz.
Import from the Music app, keeping play counts, ratings and playlists.
Find missing artwork and larger copies of covers you have.
Import CDs in AAC, Apple Lossless, FLAC or MP3, checked against AccurateRip.
Find duplicates, files that aren't in the library, and songs whose files are missing.
Several libraries, each with its own iPods and settings.
Back up song details such as play counts and ratings, and restore them.

Play on your Mac with Up Next, an equalizer, Sound Check, and audiobook speeds.
Playlists and smart playlists, and playlist files in and out.
Podcasts that check for new episodes and download them for your iPod.
Audiobooks with chapters, and several files combined into one book.
Videos converted for iPods that play them.
Photos from the Photos app (iCloud Photos included), or imported straight from digital cameras and their SD cards into ClassicTunes' own photo library, on the iPod's Photos menu.
Scrobbling to ListenBrainz from your Mac, your iPod and Rockbox.

Nothing on an iPod is written until a sync starts, and Preview Sync shows what that sync will do.
Files an iPod lists are only deleted once a database without them is safely written.
Updates never restart ClassicTunes in the middle of a sync. More about safety and privacy ›