iPod Classic sync with macOS Catalina???

iPod Classic sync with Catalina was spotty at best. I want back to Mojave and now it works fine. IF I ever go Catalina again, it will be in a partition so I can keep Mojave/iTunes working.

Sorry to say, but the only way to keep using your iPod is to NOT update to Catalina.

My saving grace was a simple erase my ‘12 MacBook Pro and reinstall Mojave via Time Machine. Now everything is back to normal and working again as it should have to begin with.

I suggest everyone does the same.

Had it syncing all night. Looked like it worked but the minute I hit apply in the AM it blanked again.

I had it set for “checked songs”. After another test, it looks like manually add music works.

for people having issues, do u have it set for manually add or checked music?

Formatted for Windows rather than Mac. All iPod classics (5? and above) would have shipped in Windows format. They worked happily on Mac, but would be reformatted to HFS+ if ever restored on a Mac.

tt2

I wonder if you’ve misunderstood. We’re talking about syncing older iPod classics with scroll wheels not touch screens. These will no longer sync with Catalina OS. With no sync there’s no restore and without restoring there’s no sync. Apple’s plan to phase out legacy devices. Bad bad move.

This is nothing new. I started working in IT in 1978, and have seen this over the years with various peripherals using various cables (parallel, USB and SCSI). I've seen it with my SanDisk mp3 player most recently. There are charging cables and syncing cables (which are more expensive). Best to verify that the cable has ALL needed pins connected to wires in the cable (some only have the most frequently used pins connected). Back in the day, some of the connectors had 30-50 or more pins, but some applications would require maybe 4-12 pins be wired. Some manufacturers save money by using less wires within the cable. There were also applications where certain pins had to be wired to different pins at the other end of the cable (called a cross-over cable); the other type is called straight-thru.

It looks like older iPod devices are no longer able to sync with Catalina, I had an Apple Support tech confirm this with me just now.

See Recover media from an iPod - Apple Community.

tt2

I've tried with all my iPods ( nano, shuffle, classic, video 5.5 ), for all the result is the same...eternally stuck on connecting. I've always restored on other machine ( windows, other mac with older OS ), perfect working on that but always stuck on catalina...what a disaster by Apple...I hope they will fix it soon because it's a serious problem for me and I can't revert to mojave...

Re: Playlist/s out of order.

Same issue happened for me. Right-click (or two-finger-click on a laptop) and select "Copy to Play Order" for EACH PLAYLIST. This took me nearly half an hour to do to for every playlist as I have a massive music collection.

It was basically a waste of time, however, as my Macbook seems to forget my iPod after it's disconnected. When I plug it back in my chosen playlists are greyed out and I only have the choice to erase & sync. Awesome (*sarcasm*).

Apple should never have given up on the iPod classic but it looks like they're passive aggressively blowing it up now.

With some degree of rigamarole, I've been able to keep my classic functioning on Catalina, though it still loses my place in my podcasts. Before I sync my iPod, I now deauthorize my Audible books, deauthorize my computer in iBooks, reauthorize my computer in iBooks, then reauthorize my Audible account in Books. Typically, I lose my place in my book as well. I think that the Mac considers the most recent listen to be on the Mac, and not on the iPod.

It's lame.

I did manage to restore a 256 Gb iPod classic that I just built using Catalina, so hopefully these are relatively easy patches for Apple.

I restored my iPod Classic on my MacBook Pro using Catalina. It did take a while - but I set it for Manual so I could manipulate the playlists/tracks.

The problem now is, when I connect my iPod Classic to a machine running Mojave (so I can still SEE the playlists on the iPod - which I cannot on Catalina), it connects, synchs, shows the tracks in Music app (RIP-iTunes) and then disconnects itself - before I get to play anything! At this point, I may just have to give up on my (formerly) beloved-iPod Classic and start using my iPhone Xr as my ipod replacement. :(

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.

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.

I am also curious for those who get it work on Catalina - what were your settings?

i can only the iPod Classic to work when on manage music manually.