I am a BIS user.
It never shows as a conflict, simply as a change from the handheld to outlook, they are set to sync. The new date shows up in Outlook while the handheld still shows none for the date
I enter my appts in both the handheld and outlook.
It does not happen every time, if there are other changes in things like the calander or addresses it is less likely to occur, but still happens on occasion. It usually sticks with the same random date for a period then it doesn't do it, and when it starts again it's using a different random date