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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

Dec 18, 2019 6:45 AM in response to CarolineCairns

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.

Dec 18, 2019 7:54 AM in response to CarolineCairns

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

Dec 18, 2019 10:04 PM in response to Najohn

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.

Dec 18, 2019 11:43 PM in response to ldweisberg

Hello Idweisberg --- just to let you know that the Tech [Senior] that I have my ongoing Case with [Australia] after 2hours looking at it a few days ago told me that the only Option May Be to Have a Small Partition operating Mojave and keep iTunes there.

And have the rest on Catalina which I am currently working under.


With all of the Billions we all spend with Apple they really need to Get a PATCH fast and give us some REAL Customer Service.

As good as the Techies are they can't Fix what if Not Fixable.




Dec 19, 2019 1:07 AM in response to whalecanes

Lessons learned from Catalina 10.15.2 sans iTunes:

  1. As with most prior updates, syncing check boxes and radio buttons had to be changed after the update (but this time in the Music, Podcasts... tabs that pop up in Finder when you click on the first (of sometimes two) iPod devices under Locations.
  2. MP3's downloaded from sources other than the Apple Store need to be copied into the Music application. Had to use "file" from the menu bar, then add to library (or short-cut command O), then navigate to location, select the MP3's, and press the open button. Dragging and dropping files did NOT work (sync could not find files) - only allows you to play in Music. Looks like the "Automatically Add to iTunes" automation either did not convert with with update, or does not work.


After these changes/actions, a circa 2008 80 GB iPod Classic and a circa 2013 160 GB iPod Classic successfully synced. A YouTube video that is floating around indicates success with an 18 year old original iPod Classic. Suspect some of my initial issues may have been due to particular setup of my former "Automatically Add to iTunes" folder, since, after running Catalina update, it contained new entries for "Automatically Add to Music" and several other entries. Maybe I just needed to change the download location in Safari. For now, just downloading MP3's to downloads, and selecting them from recents.


Did notice that Time Machine and several other items appear to run faster under Catalina. Java control panel appears to take longer to open.

Dec 19, 2019 1:02 PM in response to iolanthe3

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.

Dec 21, 2019 3:23 PM in response to danielfrombolingbrook

You may want to look at these:

For various iPods:

https://www.youtube.com/watch?v=aybDreAz6Lk


iPod 5th & 6th Gen. NANO section starts around 6 minutes 40 seconds (in this video):

https://www.youtube.com/watch?v=sm7r0pwP8Cw


I'm having no major problems on 10.15.2 Catalina with my hard-disk based 80 GB classic (circa 2008) or 160 GB classic (circa 2013), other than some podcasts (Mad Money) downloaded from Apple show up in both Music and Podcasts, and without artwork (although I've seen that sporadically in the past - may be CNBC's issue). Both have hard disks (micro disks). The 2008 model was rebuilt with a third-party replacement disk and battery about 4 years ago. Minor issues (for me) remain, but not going back to older OS. Plan to buy an iPhone next year or two (and retire iPods when either a next battery or disk goes).


Did find that podcasts added to library are being stored on the cloud, you need to go to the episodes screen and select download to get the podcast on your Mac (so it will sync with iPod). Like the speed control in Podcasts (previously had to play Music or Podcasts in Quick Time to get playback speed control). Like the adjustable time on jump forward and jump backward buttons. Would like to see this in Music application in the future.


Can understand the frustration some are having, as a tester for a company that never upgraded to Win8 or Win8.1 because of a whole slew of problems with critical software that had major issues with Win8 (a real dog) and Win8.1 versions. In my opinion, Windows has been going downhill from WinXP onward. Dumped Windows at home when they stopped supporting Outlook Express, and will never go back.

Dec 22, 2019 1:46 PM in response to WReist

Saw the videos, and thank you for the referrals. But in neither did I see any reference to iMacs. I have read several posts that talk about success syncing iPod Classics while running Catalina on a MacBook, but no one using an iMac. I'll probably stay with Mojave until I get some real concrete evidence of success with this issue on iMacs.

Dec 22, 2019 9:37 PM in response to danielfrombolingbrook

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.

Dec 24, 2019 1:55 PM in response to danielfrombolingbrook

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.

iPod Classic sync with macOS Catalina???

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