iPod Classic sync with macOS Catalina???

Forget macOS Catalina for good if it comes to syncing pre-iOS iPods. Apple is truly a drag. Since 1982 I am an Apple customer and I bought a helluva range of products. Now they cheated badly. How can I classify devices obsolete when they were sold until 2014?

I only have the following advice which hopefully solves things at this point: get a copy of Parallels Desktop software, install macOS Mojave in a virtual machine - and it syncing works the old way by using iTunes running Mojave.

I can only hope that Apple will shed their ignorance and update Catalina to enable syncing our beloved old iPods. Steve Jobs would kick the guys badly who ignored the old iPods.

Make sure that you are using the original Apple iPod cable, which should be Apple brand. That did the trick to me.

That said, in my opinion Apple is the most abusive, customer-bleeding, ominous, arrogant company that has ever existed, and it only deserves to go broke. They can make you waste weeks of your life, get your blood pressure to the stratosphere, only to force you to buy a freaking little cable.

Restored the iPod on my MacBook, which also runs Catalina and no problem recognising the iPod in the finder sidebar, and hit restore. Then plugged it into my iMac and it appeared in the finder. Took me a few hours to put all the songs back though. Waste of time but, but it solved the problem. C'mon Apple fix this problem!

Update to 10.15.1 if you haven't already done so. Syncing with Classic seems much smoother now, though still lacking any progress indicator other than watching the free space steadily tick down.

tt2

Too complicated. My advise is: Try using the original iPod white Apple cable. That simple trick did it for me. I hope this helps.

Humour an old man. See Corrupt iPod Classic - Apple Community. What are your HDD stats? I'm happy to believe that Catalina's support for iPods isn't perfect, but there is also a chance that working with the new OS has uncovered data rot you were previously unaware of.

tt2

Spent 45 mins yesterday with Apple chat support: essentially my 160gb iPod is considered ‘vintage and obsolete’ and is no longer supported by iOS. FML. You think they’d tell people these things before hand wouldn’t you?

I'm off to find a decent docking speaker.

OK.. by matter of update. My 80gb Classic appeared to have developed a fault on the disc which meant it wasn’t able to correctly boot and be recognised by Apple Music under Catalina (although I doubt it ever would have been). Luckily, I still have my iMac 2009 running High Sierra and iTunes (albeit without my main record library). I was able to use Disk Utility to reformat the iPod (using EXFAT) and after that restore iTunes to my iPod. It was a bit of a faff to do this, and I did have a number of failures (until I did the reformat). I managed to use Family Sharing on Apple Music/iTunes to get the tracks I wanted off my MacBook Pro onto my iMac and thus restored/synched onto my iPod.

iPod now works as it should, although I am not running the full library on it now.

As per my earlier posts to this thread, I couldn't sync anything to my iMac and spent ages with Apple Support getting precisely nowhere. Having just installed the latest update, 10.15.1, all of a sudden I CAN sync my iPods. Maybe this will work for you guys too?

I feel for all of you.

Meanwhile, other than the expected difficulties associated with moving things to and from my time capsule (Seriously, who has 30 hrs to wait for their computer to back up/restore from back up over wifi), I've downgraded to Mojave, and am more-or-less in fully functional iPod Classic heaven. I can sync, my stuff remembers where it left off, my podcasts stop playing when finished, my audiobooks have chapters, I can manually manage my content.

Meanwhile, the allegedly "bloated" (What is that supposed to mean anyway?) iTunes does exactly what I need it to; I'll take "bloated" and functional over streamlined but frustrating as **** any day of the week.

On the flip side, I've got to weigh how I feel about potentially never upgrading my Macs past Mojave. That will work for the next several years with the MacBook Pro I have now, but when it's time to upgrade, I don't suspect downgrading to a computer that never ran Mojave will be possible. Hopefully, Apple will have their act their act together by then.

Note to Apple: Yes, I hear you: iPod Classic is a "legacy" device, and you 'no longer support it.' I'm not asking you to support it; I can manage it on my own just fine; I just need you to not mess it up.

I would echo the view that Catalina doesn't seem to like Windows (FAT32) formatted iPods. If you cannot get Catalina to restore the iPod take a look at Corrupt iPod Classic - Apple Community. What are your HDD stats? Note that if macOS thinks a connected drive might be corrupt it can sometimes invoke disk first aid in the background, which can prevent foreground access to the device while it is being inspected or repaired.

tt2

Yes and no. In my case, a restore will successfully sync my iPod Classic (and it takes about 12hrs, since I replaced the Classic's hard drive with 400GB of micro SD cards). However, every subsequent attempt to sync fails again. So it's like a one-time refresh that's a one-way street from the computer to the iPod. Very frustrating, since all of the work I've put in to rate songs on the iPod gets lost every time I have to do this. Apple -- please, please fix Catalina's sync issues. Related: once in a while, I can't shut down in Catalina unless I go to Activity Monitor and kill all of the processes that begin with AMP: AMPArtWorkAgent, AMPDeviceDiscoveryAgent, AMPDevicesAgent, and AMPLibraryAgent -- essentially, all of the software that runs device sync with my library. So it seems pretty likely to me that the fundamental toolkit that handles device connections to Catalina is a buggy mess.

Check the devices in Disk Utility with First Aid. You may need to reformat to Mac on another system if Catalina won't play ball.

tt2

Catalina will for sure recognize the software on the classic. I have multiple versions from 5th through 7th generation, and I can get them all working. I'm not sure if the fact that all of my iPods are upgraded with a SSD makes a difference, though there's no reason I can think of that it would. The iPod isn't going to 'know' if it has a typical HDD or an SSD.

My suspicion, and I'm more-or-less totally speculating, based on what I think is a possible reasonable starting point is that the formatting on the iPod is incorrect. In particular, if an iPod was set up, for example, as a FAT32 iPod in Windows, or a Mac for that matter, Catalina won't be able to read it.

You'll note that if you have any 32 bit programs on your Mac after the Catalina upgrade, these will be grayed out, and if I recall correctly (I'm running Mojave again!!!), covered with a circle/slash combo. Apple abandoned support for 32 bit file structures with the Catalina upgrade. Thus if your iPod is set up with such a file structure, I expect it would symptoms similar to what you've described.

The fact that Disk Utility doesn't recognize the iPod is troubling though; however, this could be a function of the larger 32/64 bit issue. Perhaps Disk Utility doesn't recognize any drives formatted in that way... even if that sounds like an insane oversight to me.

With all of that said, if it were me, I wouldn't abandon hope. If none of the things you've attempted worked, I'd probably get a bit more technical. One option would be to remove the drive entirely from the iPod, put it in a caddy and hook up to your computer as a drive. Assuming the drive is functional, you should be able to get it to respond to some computer somewhere. While you have the drive out you could just upgrade to a different drive, which would force the iPod to restore since would have a blank drive. I've actually upgraded a couple of Classics to SSD recently and have had success with this method.

And with all of that said, I'll close by stating that I recognize very few people are as committed to this device as I.

Sorry, edit button not here, but I forgot to mention - make sure you check off and apply "enable disk mode".