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The same thing happened to me after I reloaded WM5 for the second time. When first sync'ing, it asked whether or not I wanted to "combine" data from the AXIM and Outlook, or to have Outlook replace data on my AXIM. I think I said "combine" and that caused the problem. However, I have many repeating occurrence items (birthdays, anniversaries, etc.) and it seemed to only create duplicate calendar entries for the current year.
Unfortunately, I had everyhting in my contact list duplicated also. I too could not eliminate the Outlook duplicates and so they just kept getting carried over to the AXIM. Finally after manually deleting the duplicates from Outlook, resetting the profile, and then NOT choosing "combine" everything seems to be working OK.
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