You may be considering syncing your iPhoto libraries between various machines using Dropbox. I tried this recently and it works, but there are some serious caveats, that if you ignore could result in wiping out a lot of your iPhoto changes. Skip to the last paragraph if you want the short version, but for those who get some strange thrill from reading a stranger’s data disaster tales, read on.

So, I recently upgraded to the 50GB Dropbox account as I wanted to be able to sync a large quantity of photos between my iMac and MacBook Pro so that I didn’t have to be tethered to the desk in order to sort and edit them, then make an iPhoto book out of them.

As I started the process of making the book I knew I would have to sync my iPhoto libraries as well. Now, I don’t use iPhoto for anything other than making calendars at Christmas, and the occasional book. I turn off the feature that copies photos into iPhotos catalogue as I prefer to leave them where they are. I also create a new library for each project (although I think that as of 2011 I’ll just keep all of each year’s projects in one library named for the year).

First of all I backed up my libraries by duplicating the entire folder in which they are kept, then zipping it down. Then I created a symbolic link to the original folder and dropped that into Dropbox. That’s a hefty amount to share so I had to leave it overnight to get the contents up onto the server and down onto my MBP.

Once done, I was pleased to see that there appeared to be absolutely no problems. Everything I’d been doing on iPhoto on my iMac prior to syncing appeared in the MBP iPhoto installation. Remembering that with such ‘hacks’ I would need to make sure only one copy of iPhoto was running at a time (to avoid save version conflicts) I got cracking on the book in iPhoto on the MBP.

Yesterday I decided I wanted to continue the book on my iMac for a change. I’d done a lot of work the day before on the book, and that evening had hidden the app away while my wife browsed the net, and then had left the laptop closed and charging on the coffee table overnight as always.

So without thinking, I fired up the iMac copy of iPhoto and as soon as the book loaded I was hit full force in the guts – none of the prior day’s work was there and with a burst of searing adrenaline I realised why.

I hadn’t quit the MBP iPhoto the night before. It was still running, with all of the changes to the book on it, albeit hidden away in the dock. I had a sinking feeling that Dropbox hadn’t been able to upload the new changes to the server and download them to the iMac.

I quickly quit the iMac app and reached for the MBP to pop out the iPhoto app from the dock where it was idling and check all was well. All my work was still there, THANK GOD. However, my mind was starting to work through what had happened.

I could see from the menu icon that Dropbox had started doing a lot of syncing on both machines. I thought through what was going on and came to the conclusion that iPhoto probably makes final saves to the library on Quit, and Dropbox is probably only able to properly sync the changes to the libraries at that point, ready to be used when the app is next launched on whichever machine. I’d closed the MBP the previous evening without quitting iPhoto and, therefore, without letting Dropbox copy the library properly to the iMac.

Then I’d launched the iMac version with an old library, from two days ago. Then I’d quit that version in a panic. And it had started syncing at that point…

With a grim feeling of doom I relaunched the MBP iPhoto and sure enough, in the last two minutes all my work had been wiped out. While Dropbox had been trying to upload the MBP’s newer iPhoto library, it had downloaded the older and freshly saved iMac library and overwritten all my work. And now the newer library was gone for good.

There was no happy ending here – I’ve thought through every possibility. My MBP is meant to be a ‘floating’ computer and hence is never backed up either locally or to the cloud, Dropbox excluded (not that it would have helped in this case for the above reasons). If I had been working on the iMac and forgotten to quit, there was a chance that the days work would have been backed up to my external drives or to Dataflame overnight, but as it was my work was toast and I’ve had to redo it today from memory.

The lessons here are:

  • when it comes to Dropbox-syncing iPhoto libraries between two machines, make absolutely DAMN sure that only one copy of iPhoto (and by extension only one iPhoto library) is being used between the two machines;
  • always make sure that when you finish on one machine you Quit the application and then physically watch Dropbox start and complete the sync between both machines;
  • make sure the DB menu icon has stopped animating on both machines, and ideally manually check the ‘modification date’ on the iPhoto library in question on the target machine before you launch iPhoto on that machine.
  • Here endeth the lesson…

    (PS, I just spent my lunch recreating the lost pages, which only numbered around 8 or so in the end, and I’m confident they’re actually better now I’ve had a second go at them. I still wish I’d never had to do it in the first place)

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