Q: I am trying to add four different sets of photos to my iPod. However, in going through the steps in the manual, I only get the LAST SET synced to my iPod. How can I get all four sets onto my iPod? What am I doing wrong?
A: The likely cause of this problem is that you are trying to load your photo sets onto your iPod individually as separate sync operations, and not including the previous photo sets.
iTunes does not merely transfer your photos onto your iPod, it actually synchronizes your photos with an existing photo application or folder of photos on your computer. Each time you sync your iPod, iTunes checks these folders and matches the iPod content to the content in your photo library on your computer. This means that if you have removed your photos from your computer, or pointed iTunes to a completely different photo folder, any photos you’ve loaded onto your iPod previously are removed unless they’re still in the folders selected by iTunes.
In basic terms, the solution to this is that you must treat your photo folders on your computer as a source library in much the same way that your iTunes library works. To synchronize multiple “sets” of photos onto the iPod, simply include them in a single photos folder, organized into sub-folders, and then specify that single parent folder for transfer to your iPod. iTunes will transfer all of the pictures contained in that main folder and any sub-folders, organizing the first level of sub-folders into separate “albums” on the iPod itself.
More information on how this all works can be found in our Complete Guide to Displaying Photos on the iPod + iPhone.