iTunes 7.2 and the MP3 gotcha

Those celebrating the beginning of the end for protected music because of the release of iTunes 7.2 and iTunes Plus may wish to holster the air-horns and pocket the ticker-tape. It turns out that while iTunes 7.2 loosens some restrictions—specifically that it can help you purchase unprotected tracks and music videos from the iTunes Store—it imposes a new restriction.

If you burn a playlist of iTunes’ protected music to a CD in iTunes 7.2 and then rip that CD in the MP3 format (a trick people often use to remove the tracks’ copy protection), those MP3 tracks won’t copy to an iPod. Try, and you’ll be told that the tracks are incompatible with the iPod.

This is not an issue with earlier versions of iTunes. I burned a copy of Joni Mitchell’s Blue that I’d purchased from the iTunes Store last month, imported the files as MP3s in iTunes 7.2, and attempted to copy them to my 80GB 5G iPod. No luck. I performed that same operation on a computer running a copy of iTunes 7.1.1 and had no problem—the files ripped and copied to the iPod flawlessly.

Before too much is made of this let me emphasize that this is an issue only with files ripped in the MP3 format and only from CDs created from iTunes’ protected tracks. If you import these same tracks using the AAC format, iPods are more than happy to accept those tracks. Likewise, an iPod has no problem taking MP3 tracks ripped from a CD burned with iTunes’ new DRM-free tracks.

Update: After testing this further, it appears that this problem crops up only when you rip the CD with iTunes. I took the CD made up of protected tracks and ripped it with Amadeus Pro to MP3 format. I brought the resulting tracks into iTunes 7.2 and they transferred to the iPod without a problem.

Update 6/1/07: This appears to be a bug. I address how to work around it in this iPodBlog entry.