Q: I have bought an iMac and can’t work out how to convert my PC iTunes library database to the Mac version of iTunes. The Mac version can’t read the PC version but I was hoping there was a way of converting the files? I have about 4 years of history in the database which I’d like to preserve.
A: Actually, the iTunes library database format is identical between the Mac and the PC. The challenge in converting your iTunes library from one platform to the other lies in two other specific areas: Moving the actual files between computers, and getting iTunes to recognize the different folder and path structure used by the other operating system.
Copying the files is generally a pretty straightforward task provided you have either a network connection between the two computers or an external hard drive of sufficient capacity for your iTunes library database and all media files.
The real problem lies in the fact that Mac OS X and Windows use completely different conventions for their file systems. For example, Mac OS X does not use drive letters. Since the iTunes database stores the complete path to each and every file in your library, this causes problems when you move your files to another platform, since the iTunes database would still be looking for the files in the old location (ie, D:\Music) which cannot possibly exist on the new operating system due to the different file system structure.
If you have allowed iTunes to manage and organize your library for you, however, there is a reasonable means to work this out. Although iTunes stores the full path to each and every file, when it cannot find a music file at that location, it falls back to looking in the default location where that file might otherwise be. This is normally in the iTunes Music folder path, in an ARTIST\ALBUM subdirectory structure, and is the same structure that iTunes itself will organize your music files into.
Therefore, if you place your entire media library in iTunes’ default location, and ensure that your iTunes Music Folder path is set to that folder, then it should be able to find all of your tracks through it’s default “fall-back” behaviour.
Note that you can ensure that iTunes has organized your music properly into its iTunes Music Folder by using the “Consolidate Library” function found under the iTunes Advanced menu. This command will tell iTunes to take all of your music files and copy them into your iTunes music folder, organizing them into the ARTIST\ALBUM subdirectory structure.
If you’re concerned with preserving your own file and folder structure and not willing to allow iTunes to manage your library structure, there will be no easy and reliable way to handle this other than reimporting all of your music into a new iTunes library, and losing all of your ratings, play lists, and play history in the process.
So, in short, the basic steps to move your iTunes library from Windows to Mac (or even vice-versa) would be as follows:
1. On the original computer, go into your iTunes preferences and select the “Advanced” tab and ensure that your “iTunes Music Folder” location is set correctly. This can either be your current iTunes Music folder, or you can choose a new path for this (on an external hard drive, for instance).
2. Select Advanced, Consolidate Library to ensure that all of your music files are consolidated into iTunes Music folder and default organizational layout. Files will be copied into the iTunes Music folder that you specified in step #1.
3. Copy your main “iTunes” folder to its corresponding location on the other computer, ensuring that the “iTunes Library.ITL” file is copied as part of this process. This folder normally lives under your “My Music” folder on Windows, and your “Music” folder on Mac OS X.
4. If your actual media content on the source computer is located somewhere outside of your iTunes folder, copy this as well to an appropriate location on the target computer.
5. Open iTunes on the target computer. You should see your iTunes library content, although you may have broken links to some or all of your files at this point, depending on whether they are stored under the main iTunes folder or in another location.
6. Select the “Advanced” tab in your iTunes preferences, and confirm that the iTunes Music Folder is set to the location where your actual music files are stored.
7. Restart iTunes, and it should be able to locate all of your music files in their default locations: Under your iTunes Music folder, in the standard iTunes-managed ARTIST\ALBUM folder structure.
You can find more information on managing and moving your iTunes library in our iPod 201 article, Managing your iTunes Library on an External Hard Drive.