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You can try Pocket Informant to delete all the entries.
Or what I have done in the past when I had problems was... if you to want to delete all contacts, then on the PC Outlook open Contacts, click on View and select by Category. Now click on Edit and do Select All, this will select all contacts in all categories. Now click on Edit and Delete. This will delete all entries in Outlook Contacts. Now sync it with your PPC and all the contacts on both PC and PPC have been deleted.
When you are deleting all contacts in your Outlook, sometime Outlook comes back with an error message of item cannot be deleted. Even though it says cannot be deleted, it still deletes it. I have like 900+ contacts in my Contacts database, so one workaround I had found was to delete couple of categories at a time.
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