Can I sync my iPod Classic?

We are loyal Apple customers and since Apple does not offer a music device that stores 160g then they should still support the past products that do have this storage, like iPod Classic, i never would have upgraded to Monterey if Iknew the hassle, headache and heart aches as I can no longer use my Classic, shame on Apple!!

This doesn't quite answer the question; I'm having the same issue with the same configuration. The iPod Classic shows up in the Finder window as an external hard drive, and there is no "Sync" button as there is with my iPhone. There is also no way to make it show up in Apple Music.

Last time I synced the iPod was before Christmas. I have 3 household devices that interface with it, and it was handy for Christmas music. There was an error, but the iPod synced anyway. It has done that a few times in 2021, but mostly I use my iPhone for music.

I have read that Apple discontinued support for the iPod Classic in Apple Music, but I have play counts stuck in the iPod, not to mention 3 devices that are no longer useful. There seems to be 3rd party software that fixes this by circumventing DRM, but I have no desire to do that, and it wouldn't seem in Apple's best interests rather than letting my iPod work.

Apple have discontinued active technical support for iPod classic, but it should still be supported for syncing locally stored DRM-free media. Content from the Apple Music subscription service cannot be used.

Try rebooting your iPod and then see if Finder will show the device as a sync target. Unless you'd previously synced with Finder with the content that is currently on the device I suspect you'll be unlikely to recover/merge the play counts.

tt2

The manual management experience in Music is very different from iTunes. You can drag and drop playlists from Music to the device, but there is no way to reorganize the content already on the device, and if you want to remove things it is one track at a time. Syncing with selected playlists will give you much better control. See Recover media from an iPod - Apple Community if you have content on the device that isn't in your library.

tt2

Thanks. It only showed “iPod”in the sidebar. But when I woke up, and it had been plugged in all night, “my iPod” showed up as well. It’s syncing now, but has been going for 15-17 hours. I appreciate all the help

I just recently updated to Monterey and, after a few minutes, my Classic showed up as a drive on the desktop and shows as “my iPod” in finder. All features are comparable to my iPhone except, of course, wi-fi accessibility.

In macOS 10.15 Catalina and later syncing duties are managed in Finder, not Music.

tt2

I’m in the same position. iPod shows in finder but gives no options. There is music on it and I can play, but I can’t figure out how to add more songs

I see my classic in the finder. How do I create and manage playlists on the iPod? I manage music manually.

The iPod should show up in two places in the Finder sidebar. The one under the heading Locations should allow you to change settings, add media, etc.

tt2

did you try to synch it with your music?

Yes. It took a while, but my whole library in now on it.