Migrating iTunes from Windows XP to Mac OS X

I decided that I wanted to move iTunes from my Windows XP desktop to my new MacBook Air. You’d think that Apple would have “a button” to do that. You’d be wrong.┬áThere are many how-to blog posts that talk about how to copy over the files. I tried a few, but none seemed to be very straight forward. Playlists and Apps seemed to be the major stumbling block.

Anyways, I found a third-party application called CopyTrans TuneSwift which worked like a charm. For only $15 bucks, it was worth every penny. It basically creates an archive of your iTunes library on the Windows side and provides a OSX utility that unarchives things on the Mac side. The instructions want you to use an external drive, but it worked fine using a shared network folder. The basic steps are:

1. Run CopyTrans TuneSwift
2. Click the Transfer button
3. Click the I want to transfer my iTunes Library to Mac button.
4. Set the target folder (removable storage or network share) and click  Start Transfer button. This takes a LONG TIME since it is archiving all the media files.
5. When the archiving step is complete a web page will open that provides a link to the Mac restore application, which you download and run on the Mac (obviously). This takes a LONG TIME too…
6. When the library is restored, you run iTunes BUT you are supposed to hold the Option key down which allows you to select the new iTunes library. Now, I think I messed up on this step, but iTunes seemed to use the new library anyways.
7. That’s it.

Everything came over as expected and my iPhone 4, iPad (first gen) and iPad 2, all connected and synced with no issues.

The one exception is Photos and it’s mainly because Apple treats them differently that audio and video media. If you’ve ever tried to get pictures over to an iOS device, you know what I’m talking about–pictures are the bastard children of iTunes for some unknown reason. Fortunately, it’s not a big hassle to get your photos over too. I created a folder on my Mac under Pictures called My Photos and copied all my photos from the Windows iTunes folder. Then, I set the iOS device to Sync Photos and pointed it to the My Photos folder. (Initially, I tried using the iPhotos folder, but it just seemed too heavy-handed. I may use that in the future once I get more comfortable with it.)

Hope this helps you!