Catalina and iPod Classic music sync

I may be a bit of a dinosaur but I still use a lovely old iPod Classic in my car daily. I plug it into the BMW media connection and the Classic’s huge hard disk means I can have loads of music and podcasts on tap.

Since the new method of handling music and podcasts in Catalina my iPod is not syncing properly. It goes into an ongoing sync cycle and I have to force it to break. Then not all the music and podcasts I have selected are copied over. Very frustrating - worked perfectly before I upgraded MacOS.

Has anyone else still using an iPod had issues with sync under the new arrangements?

Someone here said a sync with Mojave allowed them to sync with Catalina afterward.

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Thanks for your reply and the link @JohnAtl. Looks like these people have the same issue as me. Unfortunately I have updated all my Macs to Catalina and now have not got a Mojave to sync to. Have raised an issue with Apple but not holding out much hope.

Looks like the days of my trusty Classic could be numbered :disappointed:

I need to warn my girlfriend if this too, s as she has a Classic.

You might try running Mojave in a virtual machine. I use VMware for vms, but there are free solutions available.

You could do a mojave install in a VM and do the sync there?

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It appears that it is not just the iPod Classic with issues, various other older iPods are having problems as well. Big thread here in the Apple support forums…

Some are suggesting that the issue is worst with an iMac compared to MBP. Apparently I need to restore to factory settings and start again with my Classic.