Losing Calendar appointments

My wife is a professional who sees clients on the hour and makes all appointments on her iPhone and syncs with a Windows PC and Outlook 2003 for backup. Unfortunately there are appointments that are not showing up (so she assumes that time is available and schedules another. Yesterday 4 clients showed up for the same appointment time when she only had one scheduled. Either the data is not being saved in the iPhone or things are getting messed up in the sync with Outlook 2003.
Has anyone had similar problems? Thanks for your help!

Just as a heads up -- this problem effects Entourage on the Mac as well -- If you go through Sync services, entering new data on your computer rather than on the iPhone seems to make those items disappear on Entourage - and hence when synced they disappear from the iPhone as well...somewhere along the line, they disappear into the ether on iCal as well.
I have stopped using Entourage entirely, and everything is 100% perfect on iCal, Address Book.
Somewhere along the line, Microsoft and Apple have massively gotten their signals crossed. Fortunately, I don't need to use other MS products for anything else, so Entourage was the last thing to go.

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