Can't play music from my iPod Classic in the Music app on macOS Catalina

Well peeps I FIGURED IT OUT and unfortunately it's time consuming. YOU HAVE TO RESTORE THE IPOD CLASSIC!!! Yup wipe it clean and reload it all back. I have 20,000+ songs to do so that's why I mentioned time consuming but its syncing up nicely now. Just doing bits at a time.

I'm not at my Mac right now but I had an issue connecting my classic to Catalina the other day which meant I had to restore it using iTunes 12.6.5.3 in High Sierra so I could put back my iPod clickwheel games (remember those?). I'm sure Catalina is supposed to be able to sync to older devices, but it is possible this area still needs some work. I'm not so sure you should be connecting your device to your computer to play content that is stored on it and nowhere else. That is a recipe for disaster. Your iPod should only ever hold copies of content you have in iTunes. If that isn't the case see Recover media from an iPod - Apple Community before it is too late.

tt2

At present playback of manually added content stored on a device, or organisation of its content other than deletion isn't supported. Use Product Feedback - Apple to make your case for the restoration of lost features from iTunes.

tt2

sorry but I can't see any "issues" caused by Catalina, my ipod did not freeze, it is correctly read by finder and Music App, simply there is no way to play songs on the ipod with those new applications, I'll attach a screen from my music app window

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Devices now sync with finder and not music. I cannot reproduce this because I am getting a sync error that I need to investigate. Are you saying that you are trying to play. song from your iPod through the computer?

I'm not getting the iPod classic to sync period. Once connected just spins and spins. The sidebar is recognizing and my library loads and shows up. I select some playlists i wanted to add to the iPod and the apply button still is grey'd out

I am seeing the iPod in the finder/side bar. The second its connected i get spinning arrows indicating its syncing even though i haven't selected anything to sync yet. It's an apple chord connected to back of my iMac. I go an select other playlists i want to add and still the apply button is grey'd out.

Same here. I plug it in, it is recognised and is shown on the left, but it won't sync. I get

the message that the device cannot be found. Then I read on an Apple page that the devices you can connect to Catalina are iPads, iPhones and iPod Touch. None of the older models are mentioned.

I don't get the device is not found error. It shows up in the sidebar no problem. My library loads no problem. Its the minute its connected these 2 arrows are spinning around and around. I've let it go for hours this morning and let it stayed going over night and still nothing.

Oh i've been on with Apple Support twice now and believe me, they are clueless with zero answers.

Sorry I don't get it, I have to restore the ipod classic to do what? How to play with Music App an ipod classic now there isn't Itunes anymore? Even with finder it's impossible to check playlists and play music.

Why wipe it clean and reload it all back?

It is possible that some inconsistency in the library on the device is causing issues in Catalina that weren't present when it was accessed using iTunes on older versions of OS X. I too found that my classic would hang when I connected it to Catalina, and at some point it froze completely and then wouldn't restart properly after rebooting so I had to restore it. It has been fine since.

tt2

Apologies for the lack of implied caveats. "It is possible that for some user's devices some inconsistency in the library on the device is causing issues in Catalina". Like I said, when I connected mine the first time I had a window with an endless spinning radian. Others have reported similar issues and posted that restoring the device resolved things for them.

I wasn't addressing the separate issue of whether Catalina allows direct playback of the media on a connected device. I don't think anyone was suggesting that restoring the device would fix that. It is, presumably, a feature of iTunes that hasn't been brought forward.

tt2

Thanks for your reply, so now my question is: since itunes is gone, how to create, edit a playlist, or simply play a song from the ipod library with a Mac? I made it for years with itunes.

I don’t think it is just a feature, it’s how to manage an iPod classic with a mac. Do you maybe use an other application?

All device management should take place in Finder. Perhaps they are assuming you will sync the content from the new separate apps. It may be that manual device management is no longer viable. I'll have a play when I'm back in front of my Mac.

tt2

So Music shows the songs on the device, but cannot play them. There is a Sync Settings... button that opens the Finder controls for sync selections. That has a Manage Storage... button where you can select and delete content from the device. It looks like the ability to create playlists with the content already on the device is gone, along with the ability to play what it is on it through the speakers of the computer it is connected to.

tt2