So, I had been struggling with iTunes Match. Because I switched iTunes store accounts twice, I have purchased songs in my library from three different accounts. Itunes match is of course only on the one account that I am currently using. It seems as if songs which are DRM-protected, and purchased with one of my old accounts, would not upload to iTunes Match. I got in touch with support, since I thought this was crazy: I paid for the songs and I was prevented from using them in the way I wanted (uploading to iTunes Match). They confirmed my suspicion: you cannot upload songs purchased with an account that is not the one iTunes Match is purchased with. But from looking at my library, I think iTunes match is still being worked on behind the scenes. I made smart playlists for songs with different iTunes Match statusses. Since I first finished uploading my library, 114 songs have gone from 'uploaded' to 'matched'. Were it gets interesting is with the songs that would't upload because they were bought on another account. Some of those have gone from a 'not allowed' status to 'matched'. Then I tried deleting them locally and then redownload them: the downloaded song has the account changed to my current account. Not only does this go against apples own policy, it is actually very convenient for those wanting to merge their apple-id accounts. I attached some screenshots for proof. This album was purchased with ...@kabelfoon.net. Itunes match is purchased with ...@me.com. First, all songs are 'not allowed'. Then, one changes to 'matched'. After delete and re-download (look at the higher bitrate for proof of that), the account changes. First image: regular song, still on old account and not allowed. Second image: another song from the same album purchased on the same account, matched, redownloaded, account changed, DRM removed! The time of purchase is still the same as other song.