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A lot of people complain about the DRM found on music bought at the iTunes Music Store. This is quite natural, by far the biggest supplier of music files that play on iPods, iTunes only allows you to upload the files to a few iPods, burn them to a few CDs, and play them on a few computers. And you can only upload files to YOUR iPods. If someone else’s iPod is set to play music from their account, the only way to put music from your account into their iPod is to re-set that iPod to your account (which requires erasing all the music in it). And if you want to get music DOWN from an iPod, then this is basically impossible.

You can burn your iTunes purchased song to CD, then rip the CD, but this wastes CDs, takes a while, and can only be done with about 20 songs at a time. You then have to find all the playlists that include each song and replace each iTunes purchased song by each CD-ripped song in each playlist. In other words, it’s a big hassle, plus you lose sound quality, the CD is a lossless copy of the iTunes file (which is AAC-encoded), but once the CD track is encoded into MP3 (or back into AAC), it is compressed again, so quality is lost. Unless you import the CD as WAV files, which are way too big, and would reduce the number of songs your iPod can hold (and increase the hard disk space used by your song collection) by a factor of 10.

So, what can we do ?

Well, if you have a Mac, you have two other options, both of them also lossy. One is to put the iTunes-purchased song into an otherwise-empty iMovie movie, and then save it as an MP3. This has to be done one song at a time, although there are programs like FairGame that do it automatically for many songs (i.e. you tell the program what files to convert, and it converts all of them using the iMovie converting engine, instead of having you do it one at a time). It’s not lossless (unless you save the files as .WAVs), and is even bigger a hassle than burning and ripping CDs (you still have to replace each iTunes-purchased song in all the playlists where it appears, etc). The other option is a free program called DrmDumpster. It burns your songs into CDs and then rips them…and if you have a re-writable CD in there (CD-RW), it then erases the CD and burns more songs and rips them, and erases the CD again and burns more songs and rips them, etc. So you don’t have to sit there and baby-sit the computer and keep inserting new CDs - it burns all your purchased songs and rips them, using the same CD over and over, all by itself. Again, it’s not lossless, but if you have a Mac, it’s the best option.

What if you have a Windows computer ? What if you want lossless conversion ? Even better, what if you want a program that converts all your songs, and then looks through your library and replaces all playlist occurrences of each iTunes-purchased song it converted ? That would be ideal, and lucky for us, there are 2 programs out there that do just that (and they’re free!).

One such program is QTFairUse. All you have to do is open it, adjust the settings if you want (to get lossless compression, set it to output AAC files instead of MP3s), pick a back-up folder (after it’s done making non-DRM’ed versions of your iTunes-purchased files, it replaces those files in your library/playlists by the non-DRM’ed versions, and removes the DRM’ed files from your library folders), and start the conversion. It will open up iTunes, use it to play the files (at up to 10x their speed, so it should take about 20 seconds per song), record the files AAC stream as they play (i.e. the information that is encrypted by the DRM but that has to be decrypted by iTunes to play the files), and save a non-DRM’ed copy of each file. After finishing all that, it will go through your library/playlists, replace each DRM’ed song with the corresponding non-DRM’ed copy it just made, and finally dump all the old DRM’ed files into the folder you specified. You don’t even need to install the program, just download the .zip file and open up the .exe inside it and the program runs! Nothing could be easier, just make sure you have the latest version of this program and the right version of iTunes.

The other such program is MyFairTunes. Theoretically, it does exactly what QTFairUse does, as described in the previous paragraph. But I was never able to get it to work for me. I could get it to output nice perfect non-DRM’ed AAC files, but it did not put the old DRM’ed files into the folder I specified, and did not update my library/playlists. So I can’t recommend it as enthusiastically.

And one last thing, what about downloading music from an iPod onto a computer ? This is something you’re not supposed to be able to do. The following programs allow you to do it, ephPod, iLinkPod, iGadget, PodWorks, SharePod, AnaPod, and CopyTrans among others.