Internet Information Services (IIS) on the RPC proxy server controls the HTTP session authentication. When you configure the RPC proxy server, you must set the RPC virtual directory to use Basic authentication, NTLM authentication, or both Basic authentication and NTLM authentication. Outlook can send either Basic authentication or NTLM authentication for the HTTP session, depending on how you have configured the Outlook profile. The RPC proxy server Internet Server API (ISAPI) does not accept anonymously authenticated connections.
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When you use Exchange System Manager in Exchange Server 2003 Server Pack 1 (SP1) to configure RPC over HTTP, Exchange System Manager automatically configures the authentication settings on the RPC virtual directory for you.
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NTLM authentication is also known as Integrated Windows authentication.
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The authentication mechanism that you configure in your Outlook profile is used only for the HTTP session to the RPC proxy server. The authentication mechanism between Outlook and the Exchange server, when Outlook accesses the Exchange server by using RPC over HTTP, is always NTLM. It is strongly recommended that you use SSL encryption for the HTTP session to the RPC proxy server, especially if you use Basic authentication for the HTTP session. If you use SSL encryption, you prevent your user name and password from being sent in clear text. Outlook does not allow you to use Basic authentication when connecting to your RPC proxy server without using SSL encryption.
If you have a firewall that examines HTTP traffic and modifies it in any way, you may have to use Basic authentication, instead of NTLM authentication. NTLM authentication fails if the RPC proxy server does not trust the authentication information. For example, you may have a firewall that ends the session from the Internet and establishes a new session to the RPC proxy server, instead of passing the HTTPS (SSL) session to the Exchange server without modification. This process is known as reverse proxying or Web publishing. Certain firewalls, such as Microsoft Internet Security and Acceleration (ISA) Server 2004, can successfully reverse proxy or Web publish the session and still permit NTLM authentication to succeed.
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ISA Server 2000 cannot reverse proxy or Web publish the session and still permit NTLM authentication to succeed.
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Basic authentication is not affected by reverse proxying or Web publishing and works regardless of firewalls. However, if you use Basic authentication, you must type your domain, user name, and password every time that you start an Outlook session.