iPod Classic music library greyed out and won't sync

I sold three iPod classics last year because they were so problematic synching, so don't get your hopes up that I'll be able to help.

Which model iPod Classic. The first two generations were firewire and that's no longer supported by Tahoe.

Assuming it's not that old then when you connect it to your Mac does it appear in Finder? If so then restore it and see if that works. If the iPod hasn't been restored properly then it might still be tied to the previous owner's music library.

If it doesn't appear in Finder then use Activity Monitor to kill usbmuxd and ampdevice discovery agent.

If that doesn't work then try deleting AmpDevicesAgent.plist in your user library.

I'm done at this point.

Note that the reason I sold mine was not because of the problems synching from Mac to iPod, it was because of errant behaviour when synching back, particularly play counts not updating after playing tracks on the iPod.

Good luck.

Also...

If you ever do get to the point where you can synch then you will need patience. It can sit there for an unfeasible amount of time looking like it's doing nothing, or analysing, or synching. You'd be better starting with one album or a short playlist just to get started to make sure it's working ok, but that could still take ages.

Note that none of my "help" is based on Tahoe, which might include its own set of problems.