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From your question it appears that you're deploying the version of Outlook Web Access (OWA) that ships with Exchange 5.5 Server, which I'll refer to as OWA 5.5. Note that the Exchange 2000 Server version of OWA, which I'll call OWA 2000, is not supported running against an Exchange 5.5 Server back-end. There's a useful Microsoft white paper on configuring OWA 5.5 called "Planning and Deploying Outlook Web Access 5.5," available for download here. Also, make sure you're running the most recent Exchange 5.5 service pack.
One important thing to note is if you plan on having Outlook 2003 clients in this environment, you'll need to install the Exchange 5.5 CDP Patch 2657.55 from here.
Have a read through Microsoft Knowledge Base Article 301036 (HOW TO: Install and Configure Exchange Server 5.5 and the Active Directory Connector in a Windows 2000 Domain)prior to your installation to make sure you have the correct security settings configured in your environment.
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