Non-geeks: skip this post!

For the rest of us nerds, I got the following error yesterday when starting up iTunes to sync my 30gb video iPod:

“The iPod ‘insert-name-here’ cannot be synced. An unknown error occurred (-50).”

For reference, I’m using iTunes 7.7 and iPhoto 6.0.6. This error was also plaguing my Apple TV. I had recently imported some photos off a CD into my iPhoto library, so I thought that might be the culprit. I intended to stop syncing certain albums on my iPod, but in iTunes, if I highlighted the iPod and then clicked the Photos tab, I noticed my only choice was to sync “All photos and albums.” I couldn’t choose “Selected albums,” as it was grayed out. Gargh! So I unchecked “Sync photos from” and kicked off another iPod sync to clear all photos off the device…this time, no error!

So thus began a long, tedious, frustrating, face-numbing search on the Google to find out what in my iPhoto library was broken. But let me cut to the chase and say what tips I received that were promising but didn’t fix my issue:

  • Rebooting.
  • Flashing the PRAM.
  • Repairing permissions on my drives.
  • Restoring iPod to factory settings and synching again.
  • Restoring Apple TV to factory settings and synching again.
  • Holding Option+Command, clicking iPhoto, and choosing to rebuild everything within the iPhoto database.
  • Deleting the last batch of photos I imported, then try synching again.
  • Clearing ~/Pictures/iPhoto Library/iPod Photo Cache and try synching again.
  • Anger.
  • Wishing.
  • Thinking.
  • Hoping.

My saving grace was this post. It walked me through opening the ~/Pictures/iPhoto Library/AlbumData.xml file in Safari (who’d of thunk?). When I did, the top of the file reported some convoluted error which wasn’t terribly important. The strategy is to scroll to the bottom of the file and ideally there will be a photo or keyword that the XML has barfed on:

In this case, my file ended with the word “Kluvers.” I fired up iPhoto, went to iPhoto–>Preferences–>Keywords, and low and behold, I saw a keyword called “Kluvers” that I hadn’t added (must’ve gotten imported somehow with my last batch of photos)! I deleted that keyword, quit iPhoto, quit iTunes, and started iTunes again. Happy synching time - and a happy dance by me - commenced, and the “Selected albums” was available to choose again!