problem with remote outlook refusing to authenticate

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    I have a problem getting outlook anywhere to work.

    I am running sbs 2011 on the server, and outlook 2010 on the client.

    I am trying to configure outlook anywhere and the client is not connected to the domain.

    I set everything up, and outlook just keeps asking for the credentials, and will not accept them.

    I am using an SSL certificate generated by a local CA< which I know is not ideal, but the strange thing is, that I have one computer here (my computer) that is working with the same account, and same setup. What I am doing is going into MMC on server, finding the Root CA certificate, exporting it, and then following the same procedure on the client and importing the CA cert into trusted root certification authorities. I have tried to delete all traces on this company from my computer, then start the procedure from scratch to try and break it, but it just works fine. However, on the computer I am trying to set up from scratch it will not work, and also I have tried setting it up on a completely separate computer and that will not work either. What am I missing?

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