Outlook Anywhere Security Question


  • I am trying to ensure that Outlook Anywhere traffic is secured. I have an ISA 2006 server setup to allow Outlook Anywhere traffic with Basic Authentication and FBA with Windows AD.

    I have the Outlook client security tab set to negotiate authentication and encrypt, and then the connection tab, I have it set to Basic Authentication. As I understand it, this is the best and most secure mode as using NTLM authentication requires that you drop Windows 7 clients to use NTLM v1 instead of v2 which is not as secure.

    When the Outlook client connects and I ctrl+right-click and view connectivity status it reports the following...

    Auth: Clear [NTLM]
    Encrypt: Yes
    Conn: HTTPS

    I ran Microsoft Network Monitor and WireShark against the local client and the server, and it appears the AD login information is encrypted. I just wanted to verify that indeed even though Auth is saying "clear" that the encrypt and HTTPS setting are covering me on the encryption as obviously I do not want to send info in the clear. If I'm wrong, can someone also please point out wireshark and/or Microsoft network monitor filter settings for viewing the outlook authentication portion.

    Thanks in Advance.

    Wednesday, October 30, 2013 6:02 PM

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