Copying iTunes Library from Windows to Mac (or vice versa)

From our recent computer purchase – I was faced with the dilemma of migrating my rather large iTunes library from my PC to my new Mac. Of course this would be easy if you were moving from PC to PC or Mac to Mac. In both of those cases, you can just copy your music folders over and place them in the new locations (this is what I did when I moved between Macs at my old job – just copied the Music folder over a Firewire connection to the new Music folder on the new machine).

If you dont necessarily need your playlists, then you can just copy all of your music from one machine to another and import them into a new library. In my case though, I have a few ratings as well as Smart Playlists that I wanted to keep and other playlists (a party mix, our wedding mix, mixes I made Debs, etc). In the end this was actually a little easier than I thought…

  1. First of all, on the source machine, the ‘Keep your iTunes Music folder organized’ and ‘Copy files to iTunes Music Folder when adding to Library’ must be checked. You can find these under Preferences -> Advanced.
  2. If you had to make changes in Step 1, you must now Consolidate your library. This is done by selecting “Consolidate Library” from the Advanced Menu.
  3. After #2 is done, export your library from selecting “Export Library” from the File menu.
  4. On the destination machine (in my case, our new iMac), you need to create a new library. iTunes does this on its first start (or when it cant find its library). If you need to create a new library, you can easily do so by holding down the Option key when clicking on the iTunes icon.
  5. Check the preferences on the source machine – make sure you have marked ‘Keep your iTunes Music folder organized’ and ‘Copy files to iTunes Music Folder when adding to Library’.
  6. Copy all of your music from the source machine to the destination machine. In my case, I just connected to my music share, and copied them right to my Music folder.
  7. Open the source machines exported Library in some text editor. Mine was actually about 15MB…for a 40GB or so collection. I opened this exported library in Visual Studio, but you could do it in just about anything on any machine (other options of course are TextEdit, BBEdit, Notepad, etc).
  8. Open the ‘Find and Replace’ dialog of that program. In the ‘Find’ field, enter the source machines path to music. In my case it was just ‘file://localhost/D:/Music’.
  9. In the Replace field, enter the location where your new music is going (again, in my case this was ‘file://localhost/Volumes/Macintosh HD/Users/jlumpkin/Music/iTunes’).
  10. Replace all instances, and then save out this modified library.
  11. Once your music has been copied to the new machine, open iTunes on the destination machine
  12. From the File menu, select “Import…” and select the modified library file you made in Step 9.
  13. You may have duplicate smart playlists, like the ‘Recently Added’, ‘Top 25 Most Played’, etc. You can just delete the duplicates.
  14. iTunes may still need to do a few more updates, for example checking for album artwork and determine gapless playback.

This method isn’t that hard, and once you have figured it out, the process moves pretty fast. Unfourtantly, this method does NOT copy over play count, last played, skip count, etc. The only way to get this is to use the built in ‘Backup’ feature of iTunes….which will take forever if you have a large library. Of course for someone with a library my size, it would also take up close to 80CDs!

Listening To: ‘Walk This Way’ by Aerosmith


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