Outlook anywhere with Self Signed Cert Sbs 2008

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    Hey guys I am having quite the difficult time here with Outlook anywhere.
    I am using Exchange 2007 that comes bundled with SBS 2008.
    I am a little stumped as to why this is not working properly.

    I exported my certificate as a .cer
    Enabled Outlook Anywhere in Exchange.
    Set the right parameters in Exchange for the external address.
    In my outlook client I click on RPC over HTTP and put my settings.

    https:/urloutside.com (I put only 1 / because I can’t post outside URLs)
    Only use servers that have this principle name in their certificate = msstd:urloutside.com
    Ticked off on fast and slow networks
    Basic Authentication

    I press OK I put in my user email and server and click on
    check names. I get a popup asking me for my username and password.

    After a few seconds it will fail telling me that the server needs to be online in order to check the email.

    So if I press OK and try to force outlook to open I get the following error message

    There is a problem with the proxy server’s security certificate. The security certificate is not from a trusted certifying authority.
    Outlook is unable to connect to the proxy server mydomain.com. (Error Code 8).

    When I go into internet explorer and try to import my certificate I can import it correctly into trusted publishers but I cannot import it into trusted root certificates.

    I get the message saying it is imported correctly but it never shows up.

    I have tried with certmgr.msc
    Manual import by picking Trusted Root Certificates and selecting show physical stores and placing it in Local Computer and it tells me it imported successfully but it never shows up.

    I am fairly certain that is my issue but for the life of me I have no idea how to fix it.

    Anyone with any ideas?

    P.S When I go to https:/mail.ctcopieur.ca/rpc and view my certificate it is the right one. (Again 1 / because I can’t post outside URLs)
    Double P.S. This is a SELF SIGNED Certificate. I did not pay for the certificate. I have this working in Exchange 2003 perfectly fine.


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