ITunes won't update iPod

Question

iTunes works normally until i want to sync it to my iPod. Then it says the usual "updating iPod" message then freezes. Just iTunes freezes not anything else i'm doing.
Any help would be appreciated.

Answer 1

I had this same problem when trying to rebuild my iPhoto and iTunes libraries after a hard drive failure. I was able to track the problem down to a few images, that for whatever the reason, would not sync over to the iPod. They looked fine in iPhoto and didn't appear to be corrupted, so I have no idea what was wrong with them. I discovered that this was the case because I was able to sync photos by manually selecting specific photo albums, but I was unable to sync my entire photo library.
Here's the process I used to figure out what images were at fault. For each film roll in my iPhoto library, I did the following:
1. Created a temporary photo album with all of the images from that roll.
2. Told iTunes to only sync specific photo albums, not the entire library.
3. Selected the new temp film roll in iTunes for syncing.
4. If the sync worked, I knew that film roll was not to blame.
5. If I got the error, I knew that I had identified the correct roll. Then I did a one-by-one removal of images from the roll until the sync worked.
While this was a very tedious process, it did finally allow me to get my entire photo library to sync over. And, I was able to re-import the faulty images and get those to sync as well. But deleting them first and getting a fresh copy was definitely what was needed here.