About six months ago I tried as best as I could to document my experiences moving from iTunes to Windows Media Player, and my attempts to preserve as much metadata as I possibly could during the move. I was really the most concerned with my song ratings, which are central to my listening experience, but also tried to demonstrate how to move playlists and libraries over. I didn't think that my little blog entry was going to be read by that many people, but apparently I was wrong—it gained a little bit of Google-juice and I was off to the races. I now get a few mails from people a week trying to get their libraries moved over from iTunes to Windows Media Player, and now that we are quickly approaching Christmas, nervous parents have been contacting me more than ever trying to get their kid's new MP3 player stocked with music before Christmas morning.

There are a couple key things that people are having trouble with, and they all revolve around music file formats. In an ideal world, all music files would work on all devices. We all know that we don't live in an ideal world. Apple (and Microsoft) would like you to use their more locked-in formats to keep you from easily moving from device to device. Apple uses a format called AAC and Microsoft uses WMA. As expected, iTunes won't play WMAs and Windows Media Player doesn't play AACs. This makes migrating a bit of a pain.

The key is that MP3s are the lowest common denominator—both programs play MP3s without a hitch. The key is to get iTunes to convert your AAC files to MP3s. Here's how to do this:

  1. Open up iTunes.
  2. Open your iTunes preferences (EditàPreferences) and go to the "Importing" tab.
  3. Change your "Import Using" drop-down to "MP3 Encoder".
  4. Exit from your preferences and go to the main library view in iTunes. You're going to want to sort all of your music by "File Type".
  5. Highlight all of your unprotected AAC files. (You can not convert or play songs you purchased from the iTunes Music Store because of a lock Apple is forced to put on the files called "FairPlay". Ironic, huh? Please do not email me to ask for ways around this restriction—it's currently illegal to )
  6. Right-click, and select "Convert Selection to MP3".
  7. It'll take awhile…be patient.

Voila! You should now have MP3 copies of all of the music you ripped from CDs to your library. Please note that this technique does lose quality, so if you're an audiophile, you're going to want to use the good ole fashioned "rip from CD" method directly from Windows Media Player first. Just remember to tell Windows Media Player to rip to MP3—don't get stuck in this mudhole again! J