iPod Classic sync with macOS Catalina???

For Catalina users, you are not using iTunes here. The iPod will show up (when you restart it while pressing the home button) as a device in the Finder. You will be able to restore from there.

OK, so I can connect and sync my iPods (Nano 7th Generation and 4th Generation) to a MacBook Air running Catalina, but not to an iMac running Catalina. This means I could sync using the 'Air' - that's the good news. As I wanted to sync on the iMac I restored both on the 'Air' and then had another go at connecting them to my iMac. No change - just tells me 'Loading' and that's where it stops. Seems to be machine-specific for me which I can't understand. I even tried re-installing Catalina on the iMac from Recovery Mode. No change. Apple are really frustrating at times.

I did this and it solved the issue...!...... Only temporarily. I restored it and reload it and it synched fine the next time. However, the next day it was back to square one. The ipod says it's connected and synching but nothing happens, it never stops synching no matter how long I leave it connected, and it doesn't update the "recently played" playlist so it's like no info is transferred to the iMac. What a drag...

Unfortunately, this keeps happening. The lifecycle is more or less like this:

I connect the iPod Classic. It gets detected and starts synching... and never finishes, no matter how many hours it stays there, it syncs forever without finishing. I can "force eject" it and plug it again but the same keeps happening. Eventually, I restore it and sync the music again, which of course takes hours. Then it works fine, I can sync without issue, go listen to music to it, sync again and it will sync my recently played playlist with the iMac fine, and any changes in playlists will get synched....

....This however only lasts around 24 hours. Eventually, one time I plug it again it will start sync and never finishes, and it will stay that way until I restore it again. Then it will start working again for a while until it enters the synch of terror again.

This was perfectly functioning iPod Classic that never had any issue until I upgraded to Catalina. Wish I never had.

This is also happening to my iPod nano. Just to let everyone here know that I've contacted apple support and they're on it. they've downloaded loads of data and have been in constant contact so hopefully there'll be an update around this issue soon. I would suggest that if you're having this problem to contact apple so that they can get as much information as possible in order to fix it asap.

Just spoke to a Senior Technical Support technician at Apple. His suggestions that I unplug the iMac / plug it in / restart it twice made no difference. Others theories were forwarded for the issue (e.g my anti-virus software) that did not match my experiences with the iMac (won't work) and a MacBook Air (does work). So, after around 4 hours speaking to Apple over the last 10 days, I asked them to close the support ticket. My intention is to wait until future OS X updates solve the problem.

Good luck to everyone else on this thread - I hope you all manage to find a resolution.

I made sure my MacBook pro was completely uptodate. i restarted in an extra time. i then restored the iPod classic.

then no sync at all.

enabled disk use. nothing.

switched a few settings, and now it seems to be syncing. will allow it to go overnight.

if its not ok in the AM i will reach out to support.

Mine are mostly syncing fine at this point. Sometimes it syncs, but never appears as an iPod in finder, just a generic disc.

I do not manually sync songs, I’m syncing entire music library, selected podcasts, and selected audiobooks. Disk mode is not enabled.

While all of this might sound encouraging, problems, I’m still experiencing include:

1. Loss of last listened time location in podcasts.
2. Failure to stop playing at the end of the podcast, despite being set to do so.
3. Loss of chapters in audiobooks.
4. Failure to recognize podcasts as played unless the iPod is synced immediately after finishing. If I move on to another podcast, the one I’ve listened to shows up as unlistened after syncing.

The annoying thing about Apple’s response that they ‘don’t support legacy products’ like the Classic, is that I don’t need them to support it. I’m happy with it as it was, I just ask that you don’t mess it up.

You could be right about FAT32 being an issue. I reformatted mine on Windows since I have iTunes libraries on both platforms and the performance on Catalina has been useless since I did. That might also explain why restoring the devices has fixed sync issues for some.

tt2

I had this problem restoring an iPod that I upgraded with an mSATA card. My advice is to just be persistent, I managed to restore that newly constructed flashPod with Catalina, though I'd be lying if I said it wasn't a challenge.

In the future, I'll be making clones of my iPod drives, and subsequently loading the clones onto any iPods I upgrade if I have problems restoring them.

Note to Apple: You can't make me give up my Classic. I have dozens of them, and I'll figure a workaround. If I have to, I'll dual boot my Macs with Ubuntu, and download RockBox onto my classics.

I have an iPod Nano 5 15GB, an iPod Classic 150GB, and a iPod Shuffle 2GB.

The Nano shows in Music, but perpetually says 'Loading' and the 'Sync Settings' are greyed out. It also shows in Finder but perpetually says 'Loading'

The Shuffle shows in Music, but perpetually says 'Loading' and 'Sync Settings' are greyed out. It also shows in Finder but perpetually says 'Loading'

The Classic shows in Music, but perpetually says 'Loading' and the 'Sync Settings' are greyed out. It also shows in Finder but perpetually says 'Loading'

I have restored the Nano on another computer as suggested here and then once back to factory settings, plugged it back into my MacBook Pro 2016.

The Nano now still shows in Music, but perpetually says 'Loading' and the 'Sync Settings' are greyed out. It also shows in Finder but perpetually says 'Loading'. It also no longer has no music on it obviously and no way it would appear to get new music on there.

I am unwilling to repeat this with the Classic and Shuffle as although they don't have any new music at least they are still usable. I regularly update all my devices as I purchase new music and download new music (DJ mixes) every week and rely on Smart Playlists that automatically add new music to playlists.

Don’t upgrade to Catalina if you want your iPod nano to keep working. I’ve been on the phone for hours with the techies and they say they’re still working on it but I have a feeling that after 2 Catalina updates it’s unfixable but you can’t get them to admit it.

Sounds like a good plan.

A few more observations and discoveries:

1. With sync set to automatic, when iPod is connected: I think this should read when ipod is connected, AND you open the iPod in Locations within Finder. Unsure if this implies you could sync multiple/many devices at the same time (not going to try a concurrent sync to two iPod classics - not important to me).
2. Have been using a cleaner (CCleaner) for 12 years (about 6 on Win, followed by 6 on Mac). Ran analysis of Music and Podcasts on CCleaner, with supposedly nothing in the library and nothing showing on iPod. Oddly, it showed 8 files eligible for deletion in Podcasts, and more than 500 in Music. Ran the cleaner against these. Then added some music (spoken word copied from a web site) to the library, synced to iPod Classic. The iPod worked fine in Music. Reran analysis, which now showed 8 files (4 spoken word, plus 4 cover art?). Did not purge anything this second time, since results seemed reasonable. Will test Podcasts when the only Podcast I listen to resumes next week. Wonder if there were multiple versions of the iTunes library on pre-Catalina Mac, and maybe some problems internally? Also found more than 150 MB in caches, although I'd cleared several caches manually before analysis (about 65 MB returned shortly after clearing the 150 MB).
3. Bit of a learning/adaption curve, but small compared to what I've seen in the past, going from paper-tape teletype input, punched cards and toggling a program into a computer from the control panel, then to various green screen text interfaces, finally to various GUIs on various devices. I'm sure full voice and augmented reality will be another leap.

Yes. Syncing legacy devices w Catalina is now impossible. It’s Apple’s corporate decision to phase out all older devices. Terrible move and very alienating to loyal long-time customers like me who owns several Classics, Shuffles etc.

So suddenly my iPod is now synching. It took about five restores before it began working, and sometimes it doesn’t appear to be working at first — but a few minutes after the little synch spinner in the finder window sidebar has been moving, the iPod switches from “eject before disconnecting” to “synching.” The only thing I did on the computer was switch off a network waking option. I would not think the two things are at all related.