iPod Classic sync with macOS Catalina???

No chapters aren't retained on the iPod, but interestingly, are present in the Books app. As I've mentioned elsewhere in this thread, books that are longer than about 13 hours need to be downloaded in multiple files, apparently to accommodate for the loss of chapters. The iPod classic was fine with long books broken up as chapters, but apparently balks at files over a certain size, and glitches, in my experience, at about 13.5 hours into a long audiobook.

I tried the Time Machine method right after I (accidentally) upgraded to Catalina, but magically, every backup pre-Catalina was gone. I'll look into the restore screen method. Hopefully that will work for me. Thanks!

Hi EleCh

Have a 160GB Classic iPod which always did the right thing BEFORE Catalina -- syncing with iTunes no problems.

Found it in Finder in Catalina and went to Settings up top right.

All Good and still started Sync.

Then just stopped -- Pug iPod in and it shows [not the name I gave it but just iPod] in both Music and Finder.

When selected it just keeps "LOADING" --- and thats it does nothing.

Apple Supervisor Techie yesterday took over my problem and could not come up with a fix at that time.

He did state that he was not entirely certain but he thought Catalina was not recognising the iPod software.

My Case is still on going and am calling again today.

Plugged it into my Hubby's Windows 10 computer and it said that the Disk was Corrupted.

So plugged into my Mac and went to Disk Utility --- Repair --- OK but would not let me RESTORE it.

Followed all of your Steps and as I said got so Far then it would Not give me the OPTION to Restore it was greyed out.

Any hints further to this?

Cheers Susan in WA

I cant be the only one with this problem surely ---

My wife has just noticed all her music has disappeared from her music library on Catalina. She put a call in to Apple Support and was on to them for 2.5 hrs, during which time they found that it has also disappeared from the Time Machine backups as well. Techie said that “Catalina has been a nightmare”. She still has the complete library on her iPod Touch so they are sourcing third party software to drag the library back from the iPod and into Music to rebuild her music library again. I think our issue with iPod Classics is only the tip of the iceberg in terms of Catalina problems. Make sure libraries are backed up off Apple systems!

I have an iPod Nano from (I think) 2010, and it syncs quite well with my late-2013 iMac running Mojave. It loads in the sidebar in iTunes just as well as if it were an iPhone. It always works. But if I try connecting my iPod Classic 120 GB thinking it would sync right away, it just won’t. It will not show up in the sidebar of iTunes but on the Desktop, and iTunes gets the spinning beachball, which won’t stop. I never get a Restore option. Once it confused the iMac into showing up as another Macintosh HD instead of an iPod. I gave up because I had to restart several times—once in safe mode—to have everything work normally.

I like the iPod because I use it to play music in my workshop and I like to keep my 16GB iPhone 6 music-free because it constantly would get too loaded. So at this point I’ll use the Nano, but wonder if it will cease working right if I upgrade to Catalina. After reading here I don’t know if it’s Catalina that’s causing the issues listed or if it’s iPod Classics. Seems there is definitely an issue with a connected spinning HD (bad sectors?) and iMacs in general. I know back in the old days I had a Mac that had bad sectors and I had intermittent problems with it that even Disk Warrior couldn’t fix. But I’m not a tech at all.

I was thinking that since the iPod Classics were old-fashioned style hard drives and Nanos were flash drives, the Nanos would be more compatible going forward. I don't know why they wouldn't be, but I'll take your word for it.

I think what surprises me more than anything is why Apple isn't saying anything about why the iPod Classics don't interface with iMacs. They used to be so good at helping the consumers of their own products. Apparently they don't care about what used to be. I can see maybe a third party willing to come up with an adapter or dongle (I hate that word) that would make the connection positive, but haven't seen any.

Probably wise. First video is definitely a laptop. Second appears to be a Mac Pro (with Xeon chip), since there are three large, apparently high res. screens and what looks like a cylindrical Mac Pro at the far right of the video. Maybe if an issue exists, it is limited to a given generation of a specific i5, i7 or i9 chip, since the cpu controls functioning of certain i/o operations. I can remember a long time ago, a particular Intel chip gave wrong results with certain mathematical operations using hardware (fix was to alter software to run the operations instead).

Maybe a week after the holiday rush, you could get someone at an Apple store or a Best Buy Apple store to demonstrate syncing with your iPod. Better yet, if you know someone who has updated an iMac to Catalina, ask them to allow you to sync a (free) podcast or Music clip from the Apple on-line store (or other source).

As an aside, my (minor) issue with certain podcasts showing up in both Music and Podcasts may be due to my loading a folder into Music that contained both speech-based Music (actually Podcasts that I've been treating as Music) and some (free) Podcasts that were previously downloaded from the Apple store, removed from the iPod and (prior) iTunes, but retained in for future use in the folder. Suspect this may have somehow cross linked the specific podcast in the library, causing new episodes of the podcast to appear as both Music and Podcast. Doesn't bother me that much (my bad, I think). May try to fix this later.

Thanks for posting all that. I just recently received a new 128GB iPod Classic with an SSD drive. I'm still in Mojave, in which the iPod Classic loads just like my iPod Nano has—in the browser window at the left in iTunes—and syncs beautifully. In reading your post, with the convoluted procedure to work with classic iPods in Catalina, I think I'll wait to see if Apple comes up with a new update in Catalina that deals with these devices in a more seamless way. I may even try to wait for the next major system if Catalina has no further updates.

Thanks for the tips. None of them helped me. I followed all your instructions (to the extent that I could) and none of my five iPod Classics get past a spinning gear in the finder window before eventually defaulting to message - "The selected device could not be found". So, can't even get to any of the sync/apply music functions... or anything else for that matter. Been trying for several weeks now. Sad,

All of my Classics (including my 120 gb) show up in the Finder sidebar list. When I click on the first listed iPod the main window says "Loading" with a small spinning gear. It also gives me the name and info of the iPod on the top banner. Then after 5-10 minutes the Cannot Locate Device message replaces the Loading messag. Frustrating.

No good. My iPod stalls at Loading... after a while a message that the selected device could not be found& won’t allow to use the Sync Settings in ITunes or Finder.

Hope Apple fixes this or I’m not buying anything else from them after being a loyal customer for 15 years: 4 MacBooks, tons of iPhones, 4 iPads, +6 iPods, etc etc.

this lack of care and communications really frustrates and disappoints me.

I tried it with my MacBook Pro and iPod Classic and, believe it or not, it worked! It was pretty much the same way I’ve always synced my iPod with my Apple Music (formerly known as iTunes). Thanks for the help, jaj44 🙏🏼

I couldn't agree more. This is why I haven't upgraded to Catalina from Mojave. I decided I wanted my iPods (Nano and Classic) to be put to use instead of sitting in the back of some drawer.

Personally, I like my music on the iPods instead of on my iPhone. Music just clogs up my iPhone's storage. Apple can't see why longtime loyal customers like to stick with what they like and actually use and should make total sense to them. Why can't we have a portable music player besides our iPhones?

We're not denigrating iPhones for the future, we just like to get the most out of each device we have, for our own usage agenda.

and it’s not just a matter of what we’re used to. It’s actually empirically better for a lot of use cases. Here’s mine: driving. While my phone is on the dash running waze, music plays (uninterrupted by nav notifications) on my clickwheel classic. And I can’t legally touch my phone while driving in my home state, and I’m simply not going to talk to Siri to choose tracks and ratings, whereas I can do those things in the clickwheel without taking my eyes off the road.

Well said, I’m amazed at their negligence and terrible results of Catalina. Never before had I doubted upgrading OS, now I’ve lost all confidence and will long wait before any upgrade, that is if they ever fix all the issues they created!