iPod Shuffle 2G Won't Sync Music - Solution Found

Hey everyone,

I recently dug up my old iPod shuffle (2nd Gen) and wanted to load it up with some music. However, when I tried syncing it on my Mac running macOS 14.5, I ran into a frustrating issue. The sync process would get stuck at "Step 1 of 1: Determining sync changes," and no music would actually transfer.

I spent quite a bit of time troubleshooting this, and after trying various methods (like resetting the iPod, reinstalling Music, toggling Manually Manage Music, toggling Disk Use, etc.), I finally figured out what was going wrong. The problem was with the playlists I was trying to sync. Specifically, any playlist that included songs from Apple Music wouldn't sync to the iPod shuffle.

The solution? Make sure that the playlists you’re syncing only contain music that you actually own or purchased outright from iTunes years ago.

Once I removed the Apple Music tracks, the sync worked perfectly.

So if you’re having trouble syncing your old iPod shuffle, check your playlists for Apple Music songs and replace them with tracks you own.

Hope this helps someone else avoid the same headache!