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problem with remote outlook refusing to authenticate

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  • problem with remote outlook refusing to authenticate

    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?
    David Silvester
    Systems Administrator

  • #2
    Re: problem with remote outlook refusing to authenticate

    Why are you doing things the hard way when SBS does the hard work for you?
    Have you opened the Sharepoint http://companyweb? On the home page you should have an "announcement" on how to install certificates on computers and mobile phones.
    Look in Public Downloads and you should find a "Certificate Installation" package. (That is the essence of the document on Companyweb).
    TIA

    Steven Teiger [SBS-MVP(2003-2009)]
    http://www.wintra.co.il/
    sigpic
    Iím honoured to have been selected for the SMB 150 list for 2013. This is the third time in succession (no logo available for 2011) that I have been honoured with this award.

    We donít stop playing because we grow old, we grow old because we stop playing.

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    • #3
      Re: problem with remote outlook refusing to authenticate

      I have also tried that - I didn't know you could do it that exact way, but I did go on the server to public downloads, and copied the certificate installer to the client PC, then ran it.

      That still did not resolve the issue.
      David Silvester
      Systems Administrator

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      • #4
        Re: problem with remote outlook refusing to authenticate

        sorted now - I removed everything and started again.

        then I went onto the server, MMC>certificates snap-in for local computer, then exported the Root CA with default settings.

        then went to the client PC, MMC>certificates snap-in and imported the certificate into trusted root certification authorities.

        then re-set up outlook anywhere, but in the exchange over http settings, I changed authentication to basic.

        Now everything is working.

        I think part of the problem is that I have just spent 3 days solid clearing up a hacking attempt on our webserver (totally unrelated to this obviously) and my brain is a bit mushy at the minute

        Thanks for the help.
        David Silvester
        Systems Administrator

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