iTunes Tip #43
If you are like me, you are probably not a big fan of DRM (Digital Rights Management). Unfortunately, it seems it is a fact of life. We are all subject to the whims on the big record companies in what we can play where, when purchasing music online. It seems unfair that if you paid for a song that you should be able to play it on any device YOU choose.
Lucky for us that Apple has done a great job of making the DRM from iTunes as painless as possible. I love iTunes and my iPod, but there are times that I would just like to put that iTunes purchased music on another device other than my iPod. In order to do that it usually means converting the tracks to another format.
This is not possible to accomplish directly with iTunes. You can, however, burning an audio CD with iTunes of the songs you wish to convert and then import them back from the CD into iTunes as MP3s.
Here’s how:
Make a playlist of the songs you want to convert. Burn an Audio CD. Check the iTunes preferences to make sure to set iTunes to “burn” and Audio CD, not an MP3 CD or Data CD.
iTunes -> Preferences -> Advanced -> Burning tab.

Burn CD. If you have too many songs to fit on one CD, iTunes will prompt you to use multiple CDs. Once CD or CDs are burned onto disk you will want to import them back into iTunes as MP3s (or WAV, AIFF, AAC, or Apple Lossless, if you prefer one of these formats).
Make sure that your iTunes preferences are set to import using the “MP3 Encoder” or encoder of choice.
iTunes -> Preferences -> Advanced -> Importing tab. Here you can choose which encoder to use by selecting the “Import Using” drop down menu and the “bit rate” under the “Setting” drop down menu. If you want higher than 192 kbps when choosing MP3 use the “Custom” choice in the drop down menu. You can experiment with the settings here that match your desires.

Once the encoder is set for importing you can put the burned Audio CD and “rip” it back to iTunes. In many cases you may have to re-type the ID3 Tags for the songs as it may not be possible to fetch the CD track names from the Internet. Also you will have to add the tracks Album Artwork back if you want it. You can copy the artwork and text from the original purchased track in your iTunes library. Just highlight the protected track and Command (Apple key) + I to “get info” on the track and copy paste between the ID3 Tags.

Tip: There is little that can be done by the time this takes but you can save the cost of blank CDs if you do not plan on using them in a regular CD player by using CD-RW (re-writeables) instead of regular blanks.
Also their maybe some perceivable lose of audio quality. Re-encoding at a fairly high bit-rate may satisfy you here.
Note: When importing the tracks back into iTunes, make sure you do no overwrite the original protected iTunes Store files with the MP3 files unless you want to. iTunes usually asks.
Converting All Your Protected Tracks
If you are planning to convert a lot of protected tracks check out BurningThumb’s free DRM Dumpster. DRM Dumster (donationware) is not anything close to magic, but it does automate the task of burning a CD-RW and then importing your music back into your iTunes library. It will process your entire iTunes library, not just a few selections, so there’s no need for it if you only have a few songs or less than one CD’s worth of music to convert. By using a CD-RW, DRM Dumpster is able to erase and reuse a single disc to handle your entire library without you having to babysit and pop discs in and out of your optical drive.

DRM Dumpster is “donationware” and requires Mac OS X 10.2 or later, a CD-RW disc and a CD-RW-capable burner. It’s been tested with iTunes 7.

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