How to sync iPod Classic to Music App library on macOS Sonoma 14.5?

This screenshot suggests you've only selected classical music for syncing. The error message translates as:

Some items, including "Annie Melton", were not copied to the iPod "iPod (Richard Lemieux)", because Apple Music songs cannot be copied to an iPod.

DRM protected content from the Apple Music service can only be used in computers or iOS devices, and must be downloaded directly from Apple. It cannot be used transferred from computer to device, or used on an iPod classic (presumably because it lacks a secure clock or any way to reach Apple's servers to confirm your subscription status). Neither can you transfer any content that is currently in the cloud such as purchases or CD rips that you have match/uploaded to the service and then removed the local downloads.

tt2

Hi,

Have you checked Activity Monitor. Does it show that the sync is not responding - "com.apple.devicesui (music) (not responding)". I have just synced my iPod - I got the non responding message and forced quit it. The sync began and Activity Monitor showed "com.apple.devicesui (finder).

Jim

Apple Music and iTunes Match are subscription services, separate from the iCloud service that syncs photos and data for example. Do you have a subscription to one of these? Your earlier error messages suggests that you do. As noted previously content from the Apple Music service, or that is in the cloud, cannot be used on an iPod classic. Music from a previous computer will only show up in your Cloud Music Library if it was successfully matched or uploaded from that computer, or you transfer the entire library manually.

tt2

Hi,

See If your iPod isn't turning on or seems to be frozen – Apple Support (UK)

I have iPod classics and am able to sync both. Check the activity monitor as it might indicate to the sync has stalled. Select the entry a force quit then reconnect iPod. You can also try resetting iPod to original settings if you don’t have any important music on the iPod.

Jim

Hi Richard,

See Sync music between your Mac and iPhone, iPad, or iPod touch - Apple Support. Although the classic isn't mentioned explicitly it should be the same set of steps. Where do you get stuck?

tt2

See Use Sync Library with your Apple Music subscription - Apple Support. Signing into iCloud for iCloud services doesn't sign you into your iCloud Music Library (Apple Music/iTunes Match subscription).

tt2

Hi,

See this Activity Monitor User Guide for Mac – Apple Support (UK)

Jim