Wailing in the Darkness - My iTunes Debacle


I work with two different computers: my work computer (a Macbook Pro) and my personal computer (an iMac). Since I work at home, both are sitting side-by-side on the same desk 98% of the time. I’m also a big fan of music and, as such, have a respectable iTunes library chock full of goodness. The problem: I didn’t have an easy way to synchronize the iTunes libraries on both machines such that whenever I added a new track to one, it would show up in the other without my having to do anything to help it along. What follows isn’t so much a tale of frustration with technology as it is an account of one man’s slow descent into madness.

I had searched high and low for some kind of iTunes library sync tool. None of the ones I had found had received particularly stellar reviews and none of them had the “set it and forget it” thing happening, but I needed a solution. So, I purchased and downloaded SuperSync, a cross-platform Java application that purported to do exactly what I was wanting (albeit not automatically, near as I could tell). I got it installed on both machines, fired it up and began poking around the interface to see how obviously it made my particular use case. Turns out, it wasn’t obvious at all and, as I was trying to figure out how it worked, I managed to create duplicates of every single one of my tracks along side their original. In other words, before this thing ran, I had ~/Music/iTunes/SomeBand/Somesong.mp3, but now I had an additional track called “2 Somesong.mp3″, but about 8,400 times. To describe me as “upset” would have been like describing the Sears Tower as “kinda tall”. I was foamy, livid and I wanted blood. Since that was out the question, I tried to approach the problem like any self-respecting nerd: with logic and enough hubris to believe that I could fix it easily.

Between the fits of despondent wailing, I noticed something peculiar - all of the duplicate files had December 31, 1969 as their creation date. For the uninitiated, this is the date from which all Unix time stamps are calculated in seconds (currently, there have been 1285964377 seconds since that date as I type this). That meant I had a way of identifying all of the duplicate files that were generated. There was one small hitch, though — I could write a script to walk the entire directory structure and remove all of the duplicate files, but I wasn’t sure I wanted to fix this in quite so permanent a fashion since, after all, the possibility existed that I could easily trash the files I wanted to keep along with the ones I wanted gone. Then it came to me: I could move the files to the OS X Trash where, if need be, I could easily put them back if things went south.

I searched Google for how I could move files to the Trash from the command line and, sure as anything, I found it. It required issuing a command to install a Ruby package (long explanation here), but in a couple of minutes, I had the ability to move files to the Trash as required. For those who care, here’s the Python code that did the job:

Now that my music files were all back to normal and duplicate-free (and SuperSync’s worthless carcass had been eradicated from /Applications), I was still without a useful sync solution.

It has previously occurred to me that iTunes offered some sort of “Home Sharing” thing when I had upgraded to version 10 awhile back, but I never thought much of it until this point. I started poking around in the settings and discovered that if I enabled Home Sharing on my two Macs, I could stream music from my iMac to any computer on the same WiFi network (including my wife’s Macbook). Obviously, this isn’t true syncing like I’d originally wanted, but it did accomplish the goal of allowing me to have access to the same library no matter which of my computers I was using. The only kicker is that I can only add music to my iMac which serves as a second display for my Macbook Pro during the workday, but that’s circumvented easily enough by buying new tracks on my iPhone and syncing it with the iMac; when I do this, the new tracks are available in the shared library almost immediately. It’s a workaround, but a pretty painless one.

So, the morals of the story:

  • Beware of SuperSync; even if it can do what it says it can and I’m just a moron, it still makes it incredibly easy to massively hose your iTunes library and, for that reason, should be avoided.
  • Look for less-than-obvious ways in which problem solving can be made simpler.
  • RTFM (this link contains bad words - fair warning).
  • I’m very tightly wound when it comes to my iTunes library.

(Incidentally, all of my iTunes media now gets uploaded to my beloved Dropbox to ensure that it’s properly backed up on multiple machines.)

Photo by Seven Morris

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