Serious Syncing Issue - Accepted by other person

My boss (CEO of my company) missed a meeting this morning because it wasn't on her calendar. After some debugging this is what we find is happening. I need a solution to this asap.
1. Person requests meeting with CEO.
2. Her Phone gives an alert that there is an invitation but she ignores it because she's too busy for that. Her schedule is handled by her secretary.
3. The Calendar item shows up in the calendar as tentative.
4. In Outlook (2003) the secretary has access to the CEO's mailbox and calendar. Sees the calendar invitation and accepts it on her behalf.
5. Immediately, the iphone shows the syncing spinning thing at the top and the calendar item DISAPPEARS.
The only way to get it to sync back with the calendar on the iphone again is to open the original calendar item and accept it again.
What is going on? Can this be fixed? Have others had this problem (It's a difficult one to search on in the forums.)

We're having a similar problem here with several users, but instead of delting the calendar items are reverting back to tentative within a few seconds. It does this regardless how many times it is accepted from the users Outlook calendar.

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