Those who follow me on Twitter have probably read that I’ve been struggling in trying to make iTunes play nice with Dropbox. As I wrote many times here on MacStories in the past, I moved all the files and app databases I access on a daily basis into Dropbox, but iTunes was missing. I read in many forums and blog posts that making iTunes work fine with Dropbox sync across multiple computers was quite a mess, and I wasn’t sure I was ready to take the effort and spend hours messing with 80GB of music (and hours of uploads for my connection) and all those apps I have in my library. Fortunately, I don’t store movies in iTunes.

So as I wrote, I was having doubts about going Dropbox all the way with iTunes. The advantages of this method are obvious: you can sync your devices on multiple computers as long as Dropbox is updated to the latest version, you can check for app updates on any of your computers – you can add music to your library no matter the computer you’re using. With Dropbox, iTunes simply thinks it’s running on a single machine, while in fact you’re using it on multiple machines. I have a MacBook Pro and an iMac, but I’m sure the same method works on 2 or more computers.

There are some tricks you must know, however, and some steps you have to follow in order to make it work and avoid errors. iTunes is not exactly the most stable app for the Mac or the easiest to tweak: by default, it stores its database in a directory other than /Library (where most apps usually reside), it relies on a .xml library file that can easily be corrupted and if you go ahead and store app betas in your iTunes Library, you’ll have to deal with additional folders. In my experience, iTunes has turned out to be the hardest application to sync with Dropbox, but I think I’ve nailed it. Here’s how. Read more