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

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

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

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.

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

Same issue here. I cannot manage my music on my IPOD classic with the new MUSIC app in Catalina as I was able to do before with Itunes. I cannot play music from my Ipod through the new MUSIC APP neither. I have been manually managing the music on my IPOD classic for years, never sincing directly with a playlist or music library in ITUNES.

Just got off the phone with an apple tech that offered me different solutions.

1- try to go back to MOJAVE

2- try to restore my IPOD (and lose all existing music and playlist) that way I might be able to sync with new playlist created in music but not sure it will work

3- try to access and manage existing music on IPOD with ITUNES on another computer like a PC or other mac

I will try option 3 and maybe comeback with comments on that.

If any other users have update on that issue it would be nice to hear from you.

I was hoping that APPLE would just create a uptdate with music so that all the ITUNES features would still be functionnal with the new MUSIC app... doesn't seems it is going to happen... we probably are too few IPOD classic users in the world right now.

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 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

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.

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

And to confirm, you restarted your computer? You force restarted the iPod?

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

-

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

Issues here as well. My iPod classic shows on the sidebar of the new Apple Music program, but does not show up in a finder window. I used to simply drag the recently downloaded music (album) icon from the iMusic window the the Classic in the sidebar to copy files. Now nothing happens when I try to do that. Catalina and Music are a drag in this respect. I hate that options are going away. Terrible!

I hope there is a fix in the offing.

I have same problem with both my iPod Classic and newer iPod touch. The music library on the iPods show in Finder (not in Music), the playlists do not show, and I cannot play a song when I click on it. Was on the phone for HOURs with Support 10 days ago, they wrote up a ticket, came back the next Monday and took a video of my screen, and that was all I heard. Today is Thursday. They act like this is a problem unique to me, which it obviously is not.

The computer recognize the iPod, Finder displays the Library and that is all.

If going to settings>general>reset>reset all settings does not work I think a full erase and set up again might be in order.