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Outlook Prompting for Authentication Exchange 2010

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  • Outlook Prompting for Authentication Exchange 2010

    Hi Everyone,

    A few months back we installed a new server 2008 R2 machine and installed Exchange 2010 on it. This machine was setup to live alongside our current Exchange 2003 server and the idea is to slowly start migrating mailboxes over to 2010. We have so far Migrated 3 accounts choosing the largest ones first.

    One of the accounts we have migrated across always brings up the authentication prompt whenever the user loads outlook 2010. They then enter their username and password and the dialog goes away and they are then able to use outlook until the next time they restart outlook and they are prompted again.

    I have tried to work out what the problem is by going into outlook's connection status, once that login prompt appears. I noticed in this dialog that it was trying to connect to our exchange 2010 machine for type referral.

    This problem seems to affect only one user and happens when they are setup on another machine. I am starting to get to the end of things that I can try to figure out what is wrong. I would really appreciate it if anyone could point me in the right direction to fix this?

  • #2
    Re: Outlook Prompting for Authentication Exchange 2010

    How is SSL configured on Exchange 2010? Can you let us know more about the roles you have and whether services are already going via Exchange 2010 or still via 2003? What Outlook Clients? It is also worth testing autodiscover.

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    • #3
      Re: Outlook Prompting for Authentication Exchange 2010

      Hi Virtual,

      On the Exchange 2010 machine we have disabled SSL. The exchange 2010 roles we have installed are Mailbox, Client Access, and Hub Transport.

      I'm not quite sure I understand exactly what you mean by "whether services are already going via Exchange 2010 or still via 2003"? I would imagine it is still by 2003 as that is still our main mail server. When mail comes in it is received at our firewall and then the mail goes to our 2003 Exchange server. At the 2003 exchange server I believe it then determines if mail is meant for itself or for our Exchange 2010 server and then routes it there if necessary.

      The other users that have been migrated the Exchange 2010 are using a mixture of outlook 2003 and 2010 and those other users have not encountered this problem. The user that has this problem I have not been able to get them to test if this problem happens on Outlook 2003.

      The autodiscover service I believe has not been setup as it is something that I don't think we use. What is the best way of checking this?

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      • #4
        Re: Outlook Prompting for Authentication Exchange 2010

        Disable SSL?

        How exactly did you do that?

        Particularly considering Exchange 2010 will install a self signed certificate, presumes SSL is in place as do the clients.
        The whole product is designed to use SSL, and I am pretty sure you are going to be in an unsupported scenario.

        Simon.
        --
        Simon Butler
        Exchange MVP

        Blog: http://blog.sembee.co.uk/
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        Sembee is a registered trademark, used here with permission.

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        • #5
          Re: Outlook Prompting for Authentication Exchange 2010

          This type of issue come if you do not have certificate installed on local machine.

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          • #6
            Re: Outlook Prompting for Authentication Exchange 2010

            I would actually check the local password cache on the workstation...
            Please do show your appreciation to those who assist you by leaving Rep Point https://www.petri.com/forums/core/im.../icon_beer.gif

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