Dropbox and iTunes, a match made in heaven?

There’s this hashtag that goes around on Twitter, #firstworldproblems, for when you complain about something that’s soooooooo not a real problem.

My problem since Thanksgiving has been having too much media in my iTunes library, and trying to keep everything in sync across two different Mac laptops.  I know, woe is me.

Background Problem

I’ve owned a MacBook Pro for a couple of years.  I got a new MacBook Air through work just before Thanksgiving.  I also own an iPad and an iPhone 4.  And, lastly, I buy a lot of music and TV shows through the iTunes Music Store.  At last count, I’m looking at 61 GB of music, and 323 GB of video (mostly TV season passes).  That’s far more media than the Air can store on its hard drive, and it’s even more than I can keep on the Pro without running out of space for other things — like the operating system!

Initial Solution

I purchased a 1 TB external portable hard drive to store the iTunes media, as well as other large files that weren’t necessary to keep on the Air’s hard drive at all times.  I moved all of the media onto the hard drive, and pointed the iTunes library on both computers to the hard drive location.  I kept the name of the library the same on both computers, in order to keep the file paths correct.

This works for the media, with one trick.  First, if you purchase the media from iTunes Music Store on one computer, you have to remember to use the Add To Library menu option on the other computer.

However…. There were two significant new problems that come up with this method.

  1. iTunes metadata like playlists, play count, album artwork, ratings, etc. are not stored in the same location as the media library.  There isn’t a preference you can set through the iTunes UI to change the location to the external hard drive, like you can with the media library.  This meant that all those playlists that I’d meticulously constructed on the MacBook Pro weren’t ported over to the MacBook Air automatically.  I would have to export each playlist individually, bring it over to the other machine, and then import it to the other machine.  Not worth the effort.
  2. iOS apps and the sync data for your iOS devices (iPad and iPhone) are also not stored in the same location as the media library.  This meant that I couldn’t backup my iOS devices on both computers, only on the MacBook Pro, which I wasn’t taking with me to work on a daily basis, or with me when I was out of town.  No backup, no sync, nothing.

Neither problem was the end of the world, but a seemingly unnecessary pain in the ass.

(Proposed) Follow-Up Solution

I haven’t verified this as working yet, it’ll take some more time to finish all the file transfers, but… Now verified!

I have a Dropbox account, where I can store files in one location on one computer, and then have them sync up “to the cloud!” and then back down to the other computer’s same location.

If I move the rest of the iTunes library folder over to Dropbox, and then add an alias in my original location (/Users/jason/Library/Music/) that points to the Dropbox location (/Users/jason/Dropbox/iTunes/), then, in theory, I can repeat the process on the second computer.

I’ve verified that I can safely move the library from its original location to Dropbox, and have the alias (or symlink, if you prefer) pick up all of the files.  My playlists are intact on the MacBook Pro, music play counts, album artwork, etc.  I can backup my iOS devices safely.

I’m sure that it’s necessary that both computers have the same name for the hard drive (Macintosh HD), and I use the same username (jason) for both computers.  Otherwise, I expect that file paths would cause trouble.

Once the MacBook Pro finished uploading all the files to Dropbox, the files downloaded from Dropbox to the MacBook Air shortly thereafter.  Once that was completed, I switched the hard drive over to the MacBook Air and switched the file path of the iTunes metadata library to the Dropbox location using an alias.  I’ll update this post, or do a Part Two tomorrow once I’ve confirmed everything works as I’d hoped. Everything now works as I’d hoped!

Side Question #1

Why not use Dropbox to store everything, including the iTunes media?

Two reasons.  First, Dropbox storage, even with a Pro account, only goes up to 100 GB, and I’m looking at nearly 400 GB of data.  Second, even if Dropbox could store that much data, the two laptops’ hard drives would run out of room.  Thus, Dropbox can only be part of the solution, not the complete solution.

Side Question #2

Why not use Box.net to store everything?

Again, two reasons.  First, my Box.net Business account is through work, and I wouldn’t want to store all of that personal data in a company-controlled location.  Second, Box.net hasn’t come out with a desktop sync application yet for Macs.  Thus, Box.net isn’t an option here at all.

Side Question #3

How to backup the external hard drive?

That part I haven’t figured out yet.  I have to come up with another large hard drive at home that I can use as a Time Machine backup location, just for this portable external drive.  Haven’t gotten around to that yet, and that means I’m playing with fire.



  1. Comment from Chad, copied from Facebook:
    “I solve he problem with a 2 TB Synology NAS box that holds all my media. Then each device can pick and choose what it wants. What you’re really describing is one of the many reasons what iTunes and Apple suck balls. Try MediaMonkey, a lot more options including some that might solve your issues. I mean just wait until you get a real good amount of media like 180GB of music and 1TB of movies.. My NAS is two, 1TB drives confabulated and backed up nightly to a 2TB external. It’s not ‘the cloud’ but Synology offers awesome aps that let you stream content via 3G. So it’s cloud-ish. Good luck.”

  2. Jason, for the media I recently bought a Drobo FS NAS drive and stuck 2×2 TB drives in it. Gives me 1.9 TB of useable storage with all the RAID stuff and redundancy. I installed the iTunes server plugin and voila, it shows up as a share in ITunes. Now I bought a Sonos to play the same media in my living room. Not sure about your playlists and other iTunes data though.

  3. Comment from Daniel, copied from Facebook:
    “You could store everything on the external drive and just option-click the iTunes icon to select the library on that disk, skipping dropbox altogether.”

    1. @Daniel: The upside for using my Dropbox method instead of the one you suggest is that I can launch iTunes without having the external hard drive plugged in. I may not have my media, but all the metadata would be there in the local Dropbox folder. Good for browsing the iTunes Music Store and things like that.

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