You should check the permission in IIS, specifically the exchange directories. I have notice that if you have integrated authentication turned off, OWA will keep asking for a password. Let me know what you find.
Here is a great link, if you know how to set up CA's. It took me about an hour to completely setup. Not bad for a little extra security.
http://www.microsoft.com/technet/treeview/default.asp?url=/technet/columns/security/5min/5min-301.asp
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