1. Computer Skills

How to Keep iTunes in Sync Between Two Machines

Scroll to top
Read Time: 6 min

Shipping preinstalled as part of OS X, iTunes is, for me, the hub of all my music, video and other media content. iTunes not only handles the organisation and playback of my media, but also keeps track of metadata like play counts, ratings and smart playlist qualifiers such as last played date or whether a track's in my most played.

This information, unfortunately, is tied to a specific iTunes library meaning multiple installations don't share and sync with each other by default. If you use Boot Camp on your Mac, swapping between the two operating systems with a desire to iTunes can create problems if you're keen on keeping an accurate and up-to-date library. In this tutorial, I will show you two ways of keeping your iTunes library independent of commitment to just one operating system and ensure it constantly stays up-to-date.

Understanding iTunes

Before I dive in to taking a look at how to keep your iTunes library in sync, you first need to understand how iTunes manages its files.

By default, iTunes keeps all its files in a single folder, named iTunes. In both OS X and Windows, you'll find this folder in your Music directory (/Users/username/Music/iTunes/). Inside this folder you'll find the files that makes your iTunes library your own, including all of the actual audio and video files (inside the iTunes Media subfolder) and, importantly, the iTunes Library *.xml and *.itl files.

iTunes FilesiTunes FilesiTunes Files
The iTunes Library files, shown in OS X.

The iTunes Library.itl files stores metadata about your media files, including the playlist, play count and other key information that you want to preserve when accessing different installations of iTunes. The iTunes Library.xml and iTunes Music Library.xml files store some of the same information for the purpose of sharing it with other applications, so you'll also want to keep this one in sync.

Keeping these files, along with the source media itself, in sync when using Boot Camp can be achieved in two ways: through setting up some physical storage that both the OS X and Windows versions of iTunes can take turns talking to, or using Apple's iTunes Match service.

Option 1. iTunes Match

iTunes Match is a paid subscription service, launched by Apple in 2011, that offers users the ability to store all thier iTunes music, including imported songs from non-iTunes sources, and access it on multiple devices. iTunes Match also syncs metadata like play counts and playlists that you've created. iTunes Match works with OS X, Windows and even your iOS devices, but only handles music rather than the whole package of iTunes-compatible media. However, the service does cost £21.99 per year and will only work across a maximum of ten devices.

If you're happy with the limits of iTunes Match, it's fairly straightforward to set up. Firstly, open your existing iTunes library in OS X and click through Store > Turn On iTunes Match. If you don't already have an iTunes Match subscription, you'll have to sign up for one at this stage by clicking the large blue Subscribe... button and following the necessary steps.

iTunes Match is toggled on through the Store menu.iTunes Match is toggled on through the Store menu.iTunes Match is toggled on through the Store menu.
iTunes Match is toggled on through the Store menu.

iTunes Match will then scan your library and begin uploading your content to iCloud. That's it. You can then boot up iTunes in your Windows parititon, toggled iTunes Match on through the same method and your content will appear for streaming/downloading there too.

Option 2. Moving iTunes to an External Hard Drive

The second option is to use an external storage device to keep all your iTunes files on, in a format that both OS X and Windows can read and write to. This method does not have the same requirement of having an Internet connection like iTunes Match does and handles video content too, but does mean you'll have to use an external device outside of your Mac.

Step 1. Formatting

To get started with this option, first plug in your external storage device and launch Disk Utility. Select your drive, or the desired partition of the drive, in the left pane and click on the Erase tab. From the drop-down menu, select either MS-DOS (FAT) or exFAT, depending on your preference. Note that the various Mac OS Extended options will not be suitable.

  • MS-DOS (FAT) - Although FAT is one of the most widely-compatible formats, these drives will be limited to compatibility with only individual files of a size lower than 4GB.
  • exFAT - A similar format to FAT, exFAT does not have the same 4GB file size limit but may not work if you're using an older version of OS X or Windows. If you intend to keep 4GB+ HD video in your iTunes library, this is the only format that will support your media.

You can optionally choose to name your drive and then click the Erase button.

Tip: Be warned that this will delete all files on the the selected partition (or drive, if unpartitioned) and you will be unable to restore them.

Step 2. Moving iTunes Library

When you've prepared your drive (or partition) for iTunes, it's time to move your iTunes library across. Locate your iTunes folder /Users/username/Music/ and then simply copy it, in its entirety, to the root directory of the drive or partition you prepared in the last step.

Depending on the size of the folder, this may take a while. Sit back and wait until the process is complete.

Step 3. Selecting the New Library

When you've moved your iTunes folder over to your external storage device, you'll need to select it in iTunes in both Windows and OS X.

In OS X, ensure iTunes is first closed. Then, launch the iTunes app while holding down the Option key, often marked Alt, and select Choose library. Locate the iTunes Library.itl file in the iTunes folder on your external storage and hit Open. Next, reboot your Mac into Windows. Launch iTunes while holding down the Shift key and select the same file located on your external storage.

Selecting your next library in Windows 8.Selecting your next library in Windows 8.Selecting your next library in Windows 8.
Selecting your next library in Windows 8.

Now iTunes on OS X and iTunes on Windows are talking to each other using a shared library. Play songs and make playlists in Windows and the changes will be reflected next time you boot up iTunes in OS X, and vice versa.


In this tutorial, I've shown you two ways of keeping your iTunes library in sync between Windows and OS X when using Boot Camp. Both methods are fairly straightforward and ensure you can access your iTunes content without leading to inaccurate play counts or outdated playlists.

Do you have any other unique methods of keeping iTunes in sync? Let us know in the comments!

Did you find this post useful?
Want a weekly email summary?
Subscribe below and we’ll send you a weekly email summary of all new Computer Skills tutorials. Never miss out on learning about the next big thing.
Looking for something to help kick start your next project?
Envato Market has a range of items for sale to help get you started.