Courtesy of my friend Greg ... http://www.macworld.com/article/163620/2011/11/how_to_upgrade_tracks_to_itunes_match_fast.html So that will get all your low quality tracks upgraded to professional versions. (You do this after you have finished running itunes match on your computer that has your main itunes library). Here's what to do when icloud goes down and you think you just lost all those files you deleted. (First, you have backups with time machine, other cloud services, etc, right?) Create a new smart playlist (icloud downloads) with the following attributes: Media Kind is music icloud status is matched location is NOT on this computer When icloud comes back up, that playlist will contain music files not on this computer. You can select the ones you want (or all of them) and control/click or right click or two finger tap and select download to download the selected files to this computer.