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iPod Classic sync with macOS Catalina???

Side bar is recognizing my iPod classic but the second its connected it says its syncing but nothing is happening, just spinning. Left on even over night and still the same. I even selected some playlists to add and the apply button still is grey'd out. I have to force quit it to eject the iPod. Any help???

Posted on Oct 8, 2019 9:21 AM

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185 replies

Feb 15, 2020 9:35 AM in response to kulufmsmon

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.

Feb 15, 2020 12:22 PM in response to danielfrombolingbrook

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.

Feb 17, 2020 10:58 AM in response to whalecanes

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.

Feb 17, 2020 5:21 PM in response to whalecanes

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.

Feb 17, 2020 6:55 PM in response to kulufmsmon

I'm going to chime in here with my experience, even though I've not been active in this forum since I downgraded to Mojave. t


Before I downgraded, I could get all of my iPod Classics to sync with Catalina. I can't speak to anything beyond the 10.15.2 version though. I didn't downgrade because I couldn't sync, I downgraded because the behavior of my iPod was unacceptable. I've outlined those issues elsewhere in this same thread, I believe. The issues included, but were not necessarily limited to:


Failure to remember location of partially listened podcasts

Failure to stop playing at the end of a podcast, despite being set up as such

Loss of chapters in my audiobooks


I'm perfectly content with Mojave. Someday, I may install Catalina on a second partition and occasionally try to sync from there; however, I have ZERO confidence that Apple has any interest in supporting such legacy devices.





Feb 18, 2020 12:21 AM in response to kulufmsmon

iPOD CLASSIC and CATALINA Finally Getting ON TOGETHER


All Working and Syncing Perfectly after doing a DFU Restore on all of my Classic iPods 160GB.


I was helped enormously by one of the top Level Contributors. He has a entire page on how to Restore your iPod.

Mine did not SYNC at all and I had the same problems however after a few different tries at Fixes the DFU was the one that worked for me.


I am adding the page link here as it MAY JUST HELP someone.


https://discussions.apple.com/docs/DOC-10101

turingtest2

User level: Level 10 (195,378 points)

Apple Music Speciality level out of ten: 10


I have included photos of my Sync Session today to clarify that it is all working with macOS Catalina Version 10.15.3



Software Version on the iPods is Up To Date : 2.0.5



I Choose to Sync all of the iTunes Music I have just to check it all out. This shows the iPod at the start with Space Available



And here is the iPod with All of my Music stored in the old "iTunes" App and now in "Music" App.

I was having the EXACT SAME PROBLEMS with No Syncing but restoring each iPod made this possible.




Feb 24, 2020 5:59 AM in response to whalecanes

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.

iPod Classic sync with macOS Catalina???

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