Unknown Error When Syncing Photos

I received the same error and traced it down to the fact that Apple optimizes the photos for the ipod meaning that it takes each photo then creates an ipod version. This takes, depending on the number of photos you are transferring, a lot of memory and if your MAC doesn't have that much memory on the hard drive then it will generate an error. Do an info on your MAC Hard Drive and see how much available memory this is. That may be your problem. You might also can overcome this problem (don't know as I haven't tried it myself) by setting your settings or preferences to copy the photos directly meaning without optimizing them for the ipod, instead using the full size photos as they reside on your computer. Hey I'm no expert and by no means the brightest bulb on the string but if I'm not helpful maybe some other person will have a better answer for you.

I've had the same problem (see this thread: http://discussions.apple.com/thread.jspa?threadID=1160690&tstart=0). I haven't figured out any way to fix it yet, but at least we each know we're not alone now...

Also, this is a problem that's unique to my iPod Classic. My 5G 30GB didn't have this problem, even when I had to restore it a few weeks ago and re-sync all my photos at once (I have about 3900). So if it's a memory issue, it seems to me that it's an issue with the iPod Classic specifically.