Migrating Tunes from Windows to Mac OS X with iTunes

So you’ve made the jump. You have your nice pretty new Apple Mac– all the trappings– sleek computer case or body, looking like you’re ready to really jam– but what about your tunes? There are two different methods you want to use. For non-DRM files, it’s pretty straightforward, whether you were using Windows Media Player or iTunes for Windows. For DRM files– well, that’s not too complicated if you’re using iTunes previously. Read on to see.

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Non-Digital Rights Management (DRM) Protected Music/Files with a non-iTunes Library

If you were using iTunes, I’d recommend using the same method as with DRM files referenced below (Backup Library to Disc).

If your music is not protected by DRM, and you were using Windows Media Player, the matter of importing is pretty simple. Copy the MP3 collection (or other iTunes supported sound or movie file) to a temporary directory on your new Mac from the previous system, whether it’s a Windows box or an Apple box, or if it’s all on a DVD, just insert the DVD. Next, use the built in iTunes Add To Library (or <Command><O>) option. Be sure to select Copy or Move to iTunes library. Once it has copied over, verify that you now see it in iTunes, highlight one of the songs and check the info (<Command><I> or right click and choose Get Info) and verify its location. It should appear in a location similar to this: /Users/<USERNAME>/Music/iTunes/iTunes Music/<ARTIST>/<ALBUM>/<MP3 FILENAME>. Once you’ve verified it, you should be able to remove the temporary directory you copied the music over to.

Digital Rights Management (DRM) Protected Music/Files

If your music was protected by DRM on the Windows box under iTunes, it’s pretty straightforward as well, though fairly precise. If you had DRM music with some other tool (Windows Media Player?), then you need to strip the DRM somehow (try a Google search on “removing DRM from Windows Media Audio files” or something to that effect), or plan on repurchasing the music. Once you’ve stripped the DRM, then you can follow the instructions provided above.

If you’re using iTunes, if you’re using the same iTunes account on the Windows machine as on your Mac, then it’s still straight-forward, though not quite the same as non-DRM files, because they are protected by Apple’s implementation of DRM and associated with the Apple ID account.

From your Windows computer, you should plan on backing up your music files to DVD (in fact, all your files that iTunes for Windows can see if you want everything migrated). This should be available by selecting Library–>Backup to Disk. Be sure to choose Backup entire iTunes library and playlists. This will copy your iTunes library, including the DRM content associated with the authorized iTunes account, to a DVD or CDROM (e.g., the account under which the iTunes DRM files were purchased).

NOTE: If you plan on repurposing your Windows machine and will be removing iTunes from that machine, you should consider ‘Deauthorizing Computer’ on the Windows box after you accomplish this task. Apple only permits a limited number of authorized machines associated with each iTunes account.

Once you’ve backed the library up to disk, go to your new Mac, verify that the iTunes account is the same account as the old Windows one (and is authorized), and insert the disc. When you insert the disc, iTunes should start and ask if you want to restore from the disc. Choose Restore.

Once it’s done, that’s it!

Apple’s Knowledge Base article HT1382
Microsoft’s article on Digital Rights Management

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