How do I download music to an iPod classic after restoring it?

It is still possible to add music (that you own*) to an iPod Classic.

Versions of Mac OS from OS Catalina (OS 10:14) onwards do not use iTunes. To manage your iPod Classic from that computer, use the built-in Finder application. See this Apple article: Use the Finder to sync your iPhone, iPad or iPod touch with your Mac – Apple Support (UK)

* You cannot add music from an Apple Music subscription to an iPod Classic.

• • "Music that you own" means music that you have purchased from the iTunes Store, Amazon, Bandcamp etc. or obtained from the artist's website
  • Apple Music is not purchased, instead you pay monthly for access to that music. When you stop paying, you no longer have access.

Which iPod Classic do you have? The last one was produced in 2009 and was available until about 2014. I have what was originally called iPod Photo from 2004 but was retro-named Classic when the name was added to the range.

Either way, it's unlikely you will be able to move your music across to your iPod if you are using Sequoia on your Mac. At some point in the past these obsolete iPods lost touch with macOS and I have not been able to sync my audio with any recent macOS for a few years now. Instead, I have maintained an old Mac Mini with 10.13 High Sierra specifically for this purpose because syncing wasn't possible with my current Mac. The Mini is small and unobtrusive and I can connect to it from my iMac with Screen Sharing so it's a system which is working well for me at the moment.

This conversation has more to say on why the old iPods have been left behind.

The future pathway for my audio listening is to use a retired iPhone 12 (which has the current version of iOS by the way) as my iPod replacement and perhaps acquire some AirPods. I listen to audio at home so I don't need and don't like to use my current iPhone for audio. But for now, my 20+ year old iPod is powering along in partnership with my not much younger Mac Mini. On the plus side you have to acknowledge that Apple hardware lasts for ages.

Sure Lu Ann - you will be reaching a fair way too; I'm in Australia. I'm guessing you are on the other side of the Pacific?

Your iPod is model A1238, the late 2009 model and the last of the range. The other number is an order number for the black one.

It overlapped with the introduction of the iPod Touch which I never liked - it was a iPhone without the phone capability and blurred the division between the ranges. I guess it is was some customers wanted but it meant the end of the iPod.

Odd thing is that I have an iPod Nano 5th generation from 2009 somewhere (missing in action at the moment) and last time I connected it directly to my iMac it still worked as intended. I can't find it now to test it with Sequoia.

My Nano turned up. It mounted and synced satisfactorily from my Music library (formerly iTunes) using Finder. However, when I tried to do the same with my Classic it didn't even mount on my Mac. This is what has happed for some years now and which is what I think you found also.

I would have thought there might be a chance yours would mount on your Mac given that it is younger than mine and, as I said, a contemporary to my Nano which did sync.