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

I think a full revert back to Mohave is in order.

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.

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?

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?

thanks for your explanation tt2.

So established that with finder and music app is no possible to manage the ipod, how is possible to play songs on the ipod or playlists contents with the mac, now that itunes doesn't exists? Any of you has the same question? Does someone use an alternative application to manage and listen ipod music with a mac?

Same issues with my classic, including with my new ipod touch. There are plenty of classics out there to justify making this problem go away. You are not unique.

After HOURS on the phone with Support, they wanted a video and said they would get back to me. That was two weeks ago. Senior support manager told me the reset solution is not acceptable.

You are so right. When I connected my iPod classic after downloading catalina not only was it not recognised but the system wiped completely my classic, 7,469 songs backing tracks etc., lost, no appology of course or a fix of how to retrieve my content from the Apple crowd I contacted through their online "live chat" after being constantly passed to and fro from one operator to another and had to explain the problem to each operator when I got to the fifth one I gave up as none of them had any idea of how to solve the problem. the last operator I spoke to told me that the iPod classic was old tech and I should buy an iPod touch to solve the problem, but at more than £200 I'm very reluctant to spend my hard earned cash to rectify the problem that is of Apples doing. Very disappointed at the attitude cause I though I was part of the Apple family!! well that's what they told me when I bought my iMac computer, my Apple iPad, and my Apple phone. guess I was ripped off!!!!!

Are you opening finder and seeing the iPod? Are you using an Apple connector? My iPod touch 3rd gen synced once before I got the error.

Mojave is a good OS. I liked it. I have not had many issues with Catalina. Did you open Launchpad>disc utility and run first aid?

Just did and still the same. Arrows continue to spin. It's the only issue I'm having in Catalina.

Same here.

So is it official?

There is no way to use the old Ipod Classic with any apple App with Catalina?

welafever i've restarted numerous times and forced rebooted the iPod. I have to do that to disconnect it when its just spinning and spinning and nothing being done.

That is why I suggested it close to the end. it is a big step/process. Thank you for the update.