Reading all the recent threads about people having problems with iTunes 12.2, I have yet to update myself. I'm just not sure iTunes is headed in any direction I like. That said, I wondered just how far back I could take iTunes on a Mac running Yosemite 10.10.4 I've got iTunes .dmg installers back to 9.01, and a nearly virgin copy of Yosemite 10.10.4; justy enough prefs mods to make the thing tolerable, no add ons or migration asst. Turns out that if I throw out the installed version of iTunes, and the contents of the Music folder, iTunes 9.2.1 will install and run just fine. I have to allow Apps from unidentified Developers to install to get the installer to work, but after that everything is easy peasy.: iTunes 10.0.1 will install, after a dialog about an expired certificate, but crashes reliably shortly after launch. 10.2.2 does not crash and after the expired certificate dialog, runs just fine; playlists, multiple windows and all. 10.4.1 same. 10.6.3 tells me a required component is missing (dialog) each time I start it, but runs fine, cover view, multiple windows and all. 11.4 also tells me a required component is missing (dialog) each time I start it. After hitting return to dismiss the dialog, it also runs fine in it's limited little single window iOS emulation mode. It'd be a lot of work moving my library back to 10.6.3, but if things get too bad with iTunes that's still possible under Yosemite. The annoying "missing whatever" dialog could easily be dealt with automatically with a little AppleScript application that starts up iTunes then presses the return key. As end user, I'd never notice it. Earlier discussion on this board Tutorial on OSXDaily I'm not using any cloud services at all with iTunes, and seldom use the store, so I didn't check any of that stuff out. I expect there's significant loss of function down in iTunes 9.2, but you can always keep a copy of 12.2 over on some seldom booted HD for that sort of stuff.