I am having the same exact problem. Until two days ago, I have had no problems syncing any content to my iPad including photos. On 7/7, I tried adding two more photo albums to my iPad. As you detailed, it goes through the optimization process and then gives the error: iPad can not sync because the file is missing. I tried doing a restore from backup and I still get the same error. I also tried unchecking the photo albums I was trying to add thinking this might alleviate the problem. No such luck. Everything else seems to sync fine.
I have the very same problem, but for me it is worse, I had loads of photos on my iPad and when I got this problem I decided to sync just some of the photos in my collection. This resulted in the deletion of all the photos I currently had, and would not sync any at all.
Result... No pictures on my iPad
I have just tried to Sync again by opening a new folder on my PC, putting all the files in folders in that folder.
Chose it as my photo sync folder and it looked to be working.
Now I get an error.
The ipad Vince's iPad cannot be synced. An unknown error occurred (16396)
Please someone help. I cannot show off my ipod to friends. They will just take the micky out of me.
Found the solution on iLounge (thanx to auzzie23!):
1) close iphoto and itunes
2) find the iphoto library in finder, most probably located in your users folder under pictures.
3) right click on iphoto library (might be named diferently) and choose show package contents
4) delete the folder caches and ipod photo cache.
5) restart iphoto
6) restart itunes
if itunes asks that the library is linked with another ipod, say yes to the warning to re sync with your ipod/ iphone
FOR WINDOWS, GOTO THE ITUNES FOLDER LOCATED IN YOUR MY MUSIC , AND DELETE THE ITUNES FOLDER
Before you start, you need to secure a computer, of course. Once secured, plug the iPad device into the pc to start the syncing process. After plugging the device, the management screen of the iPad will show up. On this screen locate the Photos tab (uppermost part) and click on it. You should then see a Sync Photos box on top. Put a check on the box. There is a drop-down menu next to it where you can choose the folder or application that restrains the photo library. Options will vary according to what application you select and utilize. Among with these are the option to sync individual galleries and the other choice is to sync the entire photo album.
To sync one folder of photos, you can search the hard drive for the right folder to sync and then continue with syncing the entire folder or subfolders to the iPad system. Once you make sure everything is correct, you can go ahead and click the Apply button at the lower-right side of the iTunes screen to re-sync and save photos to the iPad contrivance.
Or you can refer to this page about [How to transfer iPad/iPod/iPhone contents to computer?|http://www.softwarebbs.com/wiki/IPod/iPhone/iPadTo_Computer_Transfer_%26_Backup_SoftwareReviews] It includes the transferring of music, photos, videos, SMS, Contact ect. between iPod/iPhone/iPad and computer(PC or Mac).
I was also having this problem. I also spent over an hour with tech support - told to uninstall itunes, quicktime, etc. re-install it, tried different cable and USB port, nothing made a difference. Even to reload the iPad and start from scratch. But the second i added photos back it gave me the error.
The person above had the right solution - for windows users the "iPod Photo Cache" folder is in your photo director you have selected to sync from. I simply deleted all the subfolders,files, picutres, etc. It then re-optimized it and it is working again! Hurray
I will check the forum before wasting my time with support next time.
*Sync Pictures / Photos to iPad with iTunes*
* In the iPad management screen, click the "Photos" tab at the top.
* Check the "Sync Photos" box at the top.
* From the drop-down menu next to that, select the program or folder that contains your photo library.
* Depending on what program you use, you'll have different options. These may include syncing individual galleries or your entire photo album.
* If you're syncing a folder of images, you can navigate through your hard drive to find the correct folder and then sync that entire folder or just select subfolders in it.
* Once all your settings are correct, click the "Apply" button at the bottom right corner of the iTunes window to sync again and add photos to your iPad.
* Photos will consume space on your iPad, so keep that in mind as you select between syncing all photos and individual albums and videos.
Help, I followed the instructions as listed by deleting both the iphoto and ipod photo cache and now all of my photos are gone. I haven't tried to resync either the I-Pad or I-Pod yet...and haven't deleted the trash. I yet have backups on my time machine. Shall I sync the I-Pad and I-Pod before doing a backup to laptop. We are using a MACBook.