I have this problem that I can't figure out. I have this issue that when I sync and have a backup made using iTunes on Win7 that it overwrites the previous backup and never keeps any of the previous ones. I had tried jailbreaking my touch a while ago to rearrange the icons and wallpaper and thought it was fine. I also updated the OS to 4.0 and I then noticed this problem. It may have been there before but I never looked so I don't know. I reset my Touch to factory default set up my device as new and reinstalled all my apps and then synced my contacts/calendar. But I still have this problem! When I had warranty coverage the tech support guy I spoke with was surprised at my problem and had me reset my sync history (this was when it had been jailbroken and then had the OS updated) and it allowed me to have 2 or 3 backups but then it just kept overwriting the latest one. I then did the setting up as a new device after doing a factory restore thinking that the jailbreaking screwed something up. I did keep the device name the same as I had before (not sure if that has any relationship to this) but I am now still only able to have one backup. Am I missing something here? Is there a setting somewhere that will let me have multiple backups? Any ideas of what I can try to make this work the way it's supposed to? I'm stumped here. Never having experience with Apple products before I'm coming here in hopes of getting help. Thanks for any suggestions you can give!