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Re:Why I Quit OS X – Geoff Wozniak by JohnTHaller on Sunday January 04, 2015 @12:57AM (#8833544)
Apple removed the DRM from new music sales. All existing music sold before then is still DRM locked. When Apple discontinued DRM, they made user spend $0.30 per song to unlock them (seriously). Now, it appears you can spend $25 for iTunes Match, ensure the affected songs are available, delete the local DRM-infected ones, and it will download proper ones to replace them.
Re:Why I Quit OS X – Geoff Wozniak by oneeyedpigeon on Sunday January 04, 2015 @10:32AM (#8834653)
iTunes Match brings its own issues to the party. I've had songs that I own, with 'explicit content', that I've hand-ripped, converted into radio friendly abominations that are, frankly, unlistenable. Maybe that's just Apple's 'family-friendly' values shining through; that might be appropriate for some, but I don't have a Big Brother in real life, and I don't want one messing with my music collection either!
Re:Why I Quit OS X – Geoff Wozniak by acdha on Sunday January 04, 2015 @11:09AM (#8834778)
You can redownload DRM-free versions for free:

http://www.wired.com/2014/03/kill-itunes-drm/

Re:Why I Quit OS X – Geoff Wozniak by ptman on Sunday January 04, 2015 @06:37AM (#8834143)
There were programs for removing the DRM from iTunes files. I used one successfully. Maybe they don't work anymore? I don't know.
Re:Why I Quit OS X – Geoff Wozniak by walterbell on Sunday January 04, 2015 @01:22AM (#8833599)
Or you can burn your DRM songs to CD, then rip to DRM-free MP3.
Re:Why I Quit OS X – Geoff Wozniak by danieldk on Sunday January 04, 2015 @02:02AM (#8833664)
Encoding music that has lossy compression with a lossy compressor? Not a good idea ;).