Many people have been having problems syncing photos from Windows Vista to the iPhone, as can be seen in these threads on the Apple Support Forums; “What is the official way to sincronize photos between iPhone and Vista?“, “Photos won’t sync to iPhone“, “Anyone else having problem with RAID and iTunes syncing photos in Vista?

I too was having the same problems syncing photos, until I came up with the following solution. By default, Windows Vista uses an NTFS file system, and for some reason, this causes problems when syncing photos to the iPhone. In order to sidestep this problem, you’ll

need a USB flash drive, or an external hard drive that is formatted using the FAT32 file system.

Step by step example (We’ll use C:\Documents\Pictures as our default photo directory, swap this out with your actual photo directory. We’ll use F:\ as our FAT32 formatted drive.):

  1. Copy all pictures from your current NTFS formatted drive C:\Documents\Pictures to F:\Pictures (or to a directory of your choice)
  2. Open iTunes and select the new folder that you want to use to sync photos to your iPhone – F:\Pictures
  3. Sync your iPhone and everything should work smoothly.

Prior to moving all of my files to the FAT32 formatted drive, I was only able to sync 45 out of 102 pictures, now all 102 pictures sync to the iPhone with no problem.