Yes, it's 2021, and you can still use Mavericks!

[Nightphase]

Has anyone else run into issues with iTunes on 10.6.8-10.9.5? I’ve tried to keep within legacy iTunes (10.7 and 11.4) and they cannot connect my AppleID to iTunes when pulling purchases or finding album artwork—I just keep getting “Update to the latest version of iTunes” whenever I access something that requires my ID/password.

Are these old versions of iTunes on Mavs and earlier only good for offline use anymore? This is like the main thing keeping me on Mojave and from using my white MacBook on 10.7

Apple killed off older versions of iTunes... you can't no longer login anymore, unless someone finds a workaround. I still use iTunes 10.7 for my 1550+ tracks. (You can still use it with the iTunes Remote app on iOS 15!)

 

[RinkDinkus]

Well that’s unfortunate. I relied heavily on pulling down copies of album art on iTunes for my CDs and other imports.

There was also a bunch of early 32bit apps from the early iOS days that I wanted to download from the purchased window in there. Guess I’m gonna actually have to get a 32bit iOS device to get these apps again since App Store versions of iTunes don’t exist anymore ¯\_(ツ)_/¯

 

[Grumpus]

Well that’s unfortunate. I relied heavily on pulling down copies of album art on iTunes for my CDs and other imports.

This get_cover_art python script can download cover art from Apple's servers and embed it into your music files. It requires python 3.5 or above, so you might have to install that too. I found (on Monterey) that although it embeds the cover art into your individual music files, for some reason it didn't update the artwork in the album display in the Music app. It's a simple matter to correct that with 'show song info' and 'show album info' though. I haven't tried it with iTunes, but I see no reason why it shouldn't work.

 

[RinkDinkus]

This get_cover_art python script can download cover art from Apple's servers and embed it into your music files. It requires python 3.5 or above, so you might have to install that too. I found (on Monterey) that although it embeds the cover art into your individual music files, for some reason it didn't update the artwork in the album display in the Music app. It's a simple matter to correct that with 'show song info' and 'show album info' though. I haven't tried it with iTunes, but I see no reason why it shouldn't work.

That might actually be the issue I’m having too, on my Big Sur system I literally cannot get any artwork no matter what.

 

[Grumpus]

That might actually be the issue I’m having too, on my Big Sur system I literally cannot get any artwork no matter what.

Music.app appears to not like artwork with non-square dimensions - when I imported from iTunes into Music, most of my artwork was ignored. I manually copied out each album cover from iTunes (what a pain) and used the convert program from ImageMagick to resize each jpeg to 400x400 pixels, replacing the original artwork in iTunes with the resized files. When I tried importing into Music.app again, all artwork was imported as expected. I ran the convert program on Fedora, but ImageMagick is available for macOS via Homebrew or MacPorts. Probably someone out there can suggest other ways of resizing on macOS.

You can also tell Music (via Settings) to download artwork, and eventually it will populate most album covers from Apple's servers. This can take quite a long time, possibly several days.

EDIT: you'll probably have to use MacPorts if you want to install ImageMagick on Mavericks, as Homebrew only supports current macOS versions. I personally prefer MacPorts anyway, for ...reasons.