It appears that on songs/albums that were purchased in the days of Fairplay DRM, the newly matched files when re-downloaded come through without DRM: SITUATION: I purchased Beck's Modern Guilt (not a great album) a while back and it had Fairplay DRM. If I Match, delete original file, and then re-download the new track, it appears that the DRM is gone: I tested this using Winamp, and sure-enough, the track played without issue. No more DRM! SITUATION 2: I'm just sharing this because I found it interesting... Beck's Mutations was ripped into iTunes from the CD that I own. iTunes Match is done running on my library. I have deleted the original file, and because it is in a "Matched" status, it still shows in my library as being available with the Cloud/download icon. But when I "Get Info" on one of the tracks (before I re-download), it shows an MPEG audio file at 256 kbps: Then, after I re-download the track, it shows as an AAC file: Not sure if I'd call that a bug, but it looks like iTunes is still referencing the old file until you re-download it.