Since I got my iPhone 3GS and have taken more pictures and now everytime I connect to iTunes (latest release) it re-does the Optimizing even though I don't add new pictures each time. I assumed it would after each time I added pictures but even without adding new pictures it does it. I am running on Windows Vista. I do not remember this happening before geting the new phone and uploading new pictures. With over 2,000 pictures this takes quick a while to complete each and every time I connect my phone to iTunes.