Your classic iPod,
back in sync.
A free Mac app that syncs music, videos, podcasts and photos to iPod Video, nano, mini and the original click-wheel iPods. No iTunes required.

Everything the iPod does, from a modern Mac.
iPod Pro Max writes the iPod's own database directly, the same way iTunes did, so everything shows up in the right menus on the device.
Music
Add files or import from the Music app. MP3, AAC, Apple Lossless, WAV and AIFF go straight over; FLAC and other formats are converted to AAC automatically. Album art included.
Videos
Drop in movies or clips in almost any format. They're converted to the iPod's H.264 format on the fly and appear under Videos on the device.
Podcasts
Search Apple Podcasts or paste a feed. New episodes download automatically and sync to the iPod's Podcasts menu with unplayed dots and resume positions.
Photos
Pick albums from the Photos app. Photos are sized for the iPod's screen and for TV-out, grouped into the same albums on the device.
Playlists
Build playlists in the app or bring them over from Music. Sync your whole library or just the playlists you choose.
Two-way sync
Play counts, ratings and podcast positions come back from the iPod after every sync. You can also import an iPod's contents into your library.

Supported iPods
Any iPod that mounts as a disk. Plug it in with its USB cable and it appears in the sidebar.
Not supported: iPod nano 5th generation and later, iPod shuffle, iPod touch.
Installing
iPod Pro Max is distributed directly, not through the App Store.
- Download the disk image and drag iPod Pro Max into your Applications folder.
- Open the app. It's signed and notarized with Apple, so macOS opens it without any security warnings.
- Plug in your iPod. If it asks to be restored or shows a battery icon, give it a minute to wake up; the hard drive in an iPod Video takes a few seconds to spin up.
- Add music or podcasts, then click Sync.
Questions
Can I sync my Apple Music subscription?
No. Songs from an Apple Music subscription are copy-protected and no iPod can play them. Songs you bought from the iTunes Store, ripped from CDs, or have as files sync fine. The Music import screen marks which songs are which.
Will it delete what's already on my iPod?
Not unless you ask it to. By default iPod Pro Max leaves songs it didn't put there alone. There's a per-iPod option to make the iPod mirror your library instead.
Does it work with Finder syncing turned on?
Yes, but turn off automatic syncing for the iPod in Finder so the two don't fight over the database. Finder can still see the iPod as a disk.
Where does my library live?
Your songs stay where they are. iPod Pro Max keeps a small library file, podcast downloads and converted videos in ~/Library/Application Support/iPod Pro Max.
Is it open source?
Yes. The whole app is MIT-licensed on GitHub, including the Swift implementation of the iPod database formats. Bug reports and pull requests are welcome there.
Why is a video sync slow?
Videos are converted to the iPod's H.264 320×240 format the first time they sync. Long movies take a while; the result is cached so later syncs are quick.