OS Catalina and an iPod Classic 7 (160GB) compatibility issues

I have this issue also but unfortunately have already updated all my Macs to Catalina. However, my iPod had been regularly synced with the previous MacOS so should have worked fine. Not sure where to go with this issue now.

Hello Palouse_Photog,

Thank you for using Apple Support Communities! I understand from the information you provided that you want to know if you can sync music to your iPod classic in macOS Catalina; I'd like to help.

Yes you can sync music to your iPod in macOS Catalina, here's a resource that could help:

Use the Finder to sync your iPhone, iPad, or iPod with your computer

Hope this helps.

Best Regards.

Wow. Not able to reliably sync? Sounds like not able to sync at all. Repeated 5 hour restores is not syncing.

That said, I'm sure that it is the correct answer that iPod Classic is no longer supported. But that doesn't mean apple won't fix it if there's some push back.

https://www.apple.com/feedback/macos.html

This does not work with my iPod classic like it supposed to. I am not able to reliably sync my iPod classic since converting to Catalina. I can restore my iPod classic and reload it but it won't sync after doing so (I can't add new music). Restoring is a pain because I have a large music library and it takes 5 hours to restore. Furthermore, a number of DRM restricted songs in my library that were purchased via my iTunes account won't load when I initially restore and sync the iPod. I've deleted them from the library and then downloaded them again but they still won't load.

I was on the phone with Apple Support last evening and they told me the iPod Classic was no longer supported which I know is an incorrect answer.

Thank you Apple for breaking something that worked just fine before.

What if the device does not show up in Finder? I have a classic iPod that will connect, say it needs to be restored then drop off the list like it is disconected. If I unplug it and replug it it goes through the same process. Is my iPod classic just a paper weight now?

ok, they did not fix it with me and did not call me back, BUT I did fix it.

I have a laptop that runs Mojave so I tried syncing with that, it synced fine. Once the software was restored/reset I conected to my desktop where all my music lives and it synced.

I wasted a lot of time rebooting my machine and making sure catalina was all up to date when a simple sync with another machine allowed the software to be repaired or reset. I told the Apple tech several times I had a laptop running Mojave but it took me just trying it after hanging up with Apple to get a fix. I am not pleased. It would be a fair step to sync with another machine to see if it is the ipod or the interface.

My classic shows up in finder fine, but like a disk drive only. I see what folders are on it, but get no kind of option to sync it.

This is not a real hot button for me, just one of those annoying things that should work but doesn't.

So I figure that one of these days (I'm 70+) all my Apple toys will quit working. At some point I will not be able to afford to keep upgrading.

I understand that with old devices that new tech won't work, but it would be nice if old tech would always continue to work. Be supported in any kind of fashion. How hard would have been to leave the old code in the new non-iTunes iTunes?

Well, in my case it's more OCD than anything. I was cleaning out my office and came across my old iPod. Hadn't used it seriously since about 2010. It has a vertical line across part of the display (think Apple will replace it? :) ) - but it charged right up and even has the right time! And that's without syncing! Apple toys are way too well made not to be supported into the next multiple decades. I have old music and audio books on it. Those I can play.

It was finding the thing and not being able to do what I know I should be able to do that pushed the OCD button. I am a first responder when it comes to upgrades. I have found more broken code over the years than I can shake a stick at because I always load the latest and greatest.

Good luck on your issues. When I head to work tonight, I will have my iPhone 8+ with me instead of the iPod.

Thanks for the info... I have wasted the weekend trying to get my 160gb classic synced- having put in my new car on Friday to confirm it worked fine with apple play etc.. I was so excited I plugged it in to Catalina to update my tunes and it died and wouldn't eject.

I'll try and restore the classic on my sons mac pro laptop, which I hope hasn't been upgraded to Catalina yet and maybe I can emulate your success.

I'll feedback on the results to this community

Complain.

https://feedbackassistant.apple.com