iPod sync woes

[Grumpus]

After "upgrading" my 2019 MacBook Air from Mojave 10.14.6 to Monterey 12.5 today, I discovered that Monterey's Finder can't sync any of my 3 iPods. I put "upgrading" in quotes for the obvious reason, but also because I really did a clean install and then laboriously copied my iTunes media files into the Music and Podcast apps.

Attempts to sync an iPod return immediately with no error message and no data transfer. Trying to restore an iPod (to rewrite the firmware) results in the device being wiped and the restore never finishing. When this happens, Monterey doesn't want to reboot, complaining that an operation on an IOS device is still in progress. None of these iPods are IOS devices, but whatever. I had to resort to the terminal to shut the laptop down.

Anyone out there have a suggestion for getting Monterey to the right thing?

 

[haralds]

Hmm, all mine sync to some very old ones.
Playlists were acting weird. I would start with dropping files manually.

 

[Grumpus]

Thanks for the reply haralds. Do you mean using the "manually manage" setting? I'll try that, but in the meantime I've used Retroactive to install iTunes 12.9.5, and it's syncing all 3 iPods (4th gen Photo, 2nd and 7th gen Nanos) with no problems. I certainly prefer iTunes, to put it mildly, but it might not be the best long term solution.

 

[Grumpus]

I did some testing today with an "unsupported" mid-2010 15" MacBook Pro using OCLP v0.4.10, and saw the following:

• After a clean install of Monterey 12.5, none of my iPods can be synced by Finder.
• After a clean install of Monterey 12.4, all of my iPods can be synced by Finder.
• After upgrading 12.4 to 12.5, syncing still works.

Clearly something is amiss with 12.5.