DRM Dumpster (Freeware)
DRM Dumpster is the legal way to convert DRM tracks from your iTunes music library to standard files. DRM Dumpster uses a CD-RW and iTunes itself to convert all of the DRM music files in your library or in a play list of your choice to files that you can use with any music player. With DRM Dumpster you can create MP3, AAC, Apple Lossles, AIFF, or WAV files from your DRM files.
DRM Dumpster uses the iTunes importers and selects the importer that you want to use without changing any of the import settings. To see or change, for example, the MP3 Import settings do this before running DRM Dumpster:
Launch iTunes
Open the Preferences
Select Advanced
Select Importing
Select Import Using: MP3
Choose your prefered import settings
DRM Dumpster will use your iTunes import settings, it does not change them.
Since DRM Dumpster supports any iTunes importer you need to make sure the settings for the importer that you want to use are correct before running DRM Dumpster.
Using DRM Dumpster is easy:
Launch DRM Dumpster
Select the format that you want to import from the popup list
Select the play list that you want to import from the popup list
If you are using a non-English iTunes enter your language equivalent for the word Protected
Click the Dump DRM button
Insert a CD-RW
DRM Dumpster does the rest for you. When the operation is complete you will have a new playlist in iTunes that contains the imported files.
If any problems occur during conversion (CD errors, Disk full, etc.) simply correct the problem (get a new CDRW, free up some disk space, etc.) and start DRM Dumpster again to continue from the last point.
Even if you buy more iTunes DRM protected files simply run DRM Dumpster to convert those tool.
Free download DRM Dumpster
FairGame (Freeware)
FairGame will convert the songs you bought on the iTunes Store to an unprotected format (using iTunes default encoder) and keep all the original metadata, lyrics and artwork.
FairGame doesn't do lossless DRM stripping. It re-encodes protected AAC files purchased in iTMS into unprotected AAC file using Apple's iMovie software.
More details on FairGame
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