iPod Classic won't sync with Ventura 13.0.1

Restart the Mac, making sure the option to reopen windows is not selected.

Take a look at Corrupt iPod Classic - Apple Community. There is just a possibility that a background process on the Mac is trying to inspect the classic's hard drive. If your stats indicate there are pending sectors to clear that would also suggest there are outstanding file system repairs to be performed.

tt2

An iPod classic is a USB drive, with some additional hardware and firmware. You might try leaving the MacBook on charge overnight with any power saving options turned off and the iPod connected. Or you could try explicitly running Disk First Aid on it.

tt2

Hello TT2. I'm VERY grateful to you for posting the above. The inability to add the tracks I'd imported to iTunes onto my iPod after the upgrade to Ventura was leading me to contemplate desperate measures (no Time Machine back up of Monterey... ). I was on the verge of giving up but then found, inspired by the above, that if I loaded it in Finder first, yes, it then accessed the iPod in Music and I could add. Next issue was how to ensure artwork was loaded, how to delete and replace if it wasn't, and yes, it's all doable via Music.

It's funny because when they first ditched iTunes in favour of Music, I hated it in comparison and so installed old iTunes software. Now I'm just grateful that I can still keep my twin iPod 160gb Classics (one with 256gb upgrade) going a little while longer until they die!

I never thought several years ago when it was all about iTunes and I could spend hours curating my iPod (I had one 160gb only and couldn't get more than 20k tracks on it, so was constantly deleting and refining) that I would look back at that as a golden age of portable music usage. I always thought there'd be some super high def, affordable new device with lossless quality sound and a huge memory... It's a niche market of over-priced ugly devices that cost a fortune, no thanks. One day I know I'll have to give up and resort to only using the smart phone like everyone else, but I am putting that day off as long as I can.

Once again, very grateful indeed for the help above in allowing me to do that. Long live the iPod Classic, a beautiful device.

Fuse install the solution?

Perhaps there is a workaround; neither my macbook 2010 and Macbook 2017 could recognize the iPod classic 20GB when connected thru usb-2, usb-3 and usb-c cables. The MBP's muttered when connected to the iPod and nothing emerged, though the iPod registered a connection and suggested a wipe and restore. Then I got the idea to install Fuse through homebrew; so I entered brew install fuse... in the terminal. Also installed macfuse and restarted the MBP 2017. To be on the safe side. After that my MacBook Pro simply recognized the iPod and Apple Music and iTunes registered the music in the iPod, with all different kind of connectors. I was happy as I used the iPod for some interviews long time ago and for archiving my digitized LP collection (started in 1975). Yes, I was happy to be able to back up my files from my iPod classic.

Try rebooting the machine with the Pod connected in case the behaviour is any different. Or try with the iPod in disk mode. Did you check out my earlier Corrupt iPod Classic - Apple Community link? It would be good to know if there are any pending sectors.

tt2

iPods will no longer work with Monterey either. Get a flash drive with lots of space then load it with Big Sur or earlier. Use the flash drive just for managing ipods.

Good there are no pendings. I'm afraid I don't have any other thoughts on this open in another window issue, except that I don't think you are alone. I've seen a few similar threads. You could try Official Apple Support in case it is something they can recognize and have a fix for.

tt2

Did you miss the bit where three different users in this thread mentioned being able to sync iPod classic with Finder in Ventura? You should be able to do it too. If you really want to go back, and have a suitable backup, see Restore your Mac from a backup - Apple Support.

tt2

OK, what exactly happens when you try to sync content to your iPod with Finder? For me the device shows up twice, once with its proper name, and once in caps with no more than 11 characters. The first one is the one that lets me manage content.

I can only sync locally stored files that haven't come from the Apple Music service, but it does work.

tt2

See Recover media from an iPod - Apple Community.

tt2

Ventura back to Monterey, so that I can load my Ipod Mini. I wouldn't have upgraded to Ventura had I known my Ipod wouldn't load.

Make sure all of your tracks have embedded artwork. If the files show with artwork in Finder before you copy them to the iPod then they should show with art on the device.

tt2