Announcement

Collapse
No announcement yet.

Outlook Anywhere losing proxy settings, Autodiscover issue?

Collapse
X
  • Filter
  • Time
  • Show
Clear All
new posts

  • Outlook Anywhere losing proxy settings, Autodiscover issue?

    I have Exchange Server 2010 in Small Business Server 2011. I have several remote clients that are not part of the SBS domain, but they use Outlook Anywhere to connect to Exchange.

    We originally started with a self-signed and eventually added a GoDaddy SSL certificate. Some of the remote clients lose the settings for Outlook Anywhere randomly. The proxy checkbox is unchecked and the MSSTS settings have all disappeared.

    I investigated this and it seems to point to autodiscover. Our DNS is hosted externally so I created an A-Host record at Netowork Solutions called autodiscover and resolved it to the static IP address of the server. When I did this the remote clients started to get certificate security warnings.

    Next I tried to create a CNAME called _autodiscover for mail.mydomain.com and this didn't work either, certificate security erros

    Is my Outlook Anywhere issue an 'autodiscover' problem and if it is, what amI doing wrong? Here are some additional details:

    Self-signed certificate is mail.mydomain.com. GoDaddy Class 2 certificate authority has identified this site as mail.mydomain.com. The connection to the server is encrypted.

    Network Engineers do IT under the desk

  • #2
    Re: Outlook Anywhere losing proxy settings, Autodiscover issue?

    If you only have a single name SSL certificate you need to have an SRV record for Autodiscover - a CNAME is no better than an A record if you don't have Autodiscover.example.com on the certificate.
    http://semb.ee/srv

    As this is SBS, also ensure that you installed the certificate using the wizard in the SBS console, rather than though Exchange.

    Simon.
    --
    Simon Butler
    Exchange MVP

    Blog: http://blog.sembee.co.uk/
    More Exchange Content: http://exchange.sembee.info/
    Exchange Resources List: http://exbpa.com/
    In the UK? Hire me: http://www.sembee.co.uk/

    Sembee is a registered trademark, used here with permission.

    Comment


    • #3
      Re: Outlook Anywhere losing proxy settings, Autodiscover issue?

      I tried the SRV record and got certificate security warnings. Should I have a different cert from a single domain SSL?
      Network Engineers do IT under the desk

      Comment


      • #4
        Re: Outlook Anywhere losing proxy settings, Autodiscover issue?

        You must have the SRV record wrong.
        Do ensure that you have removed the other Autodiscover DNS entries and that https://example.com/Autodiscover/Autodiscover.xml does not work (ie the root of the domain).

        The SRV record must point to the host name on your SSL certificate.

        The other option is to replace the certificate with a UC type certificate which will allow you to include Autodiscover.example.com as one of the additional names.

        Simon.
        --
        Simon Butler
        Exchange MVP

        Blog: http://blog.sembee.co.uk/
        More Exchange Content: http://exchange.sembee.info/
        Exchange Resources List: http://exbpa.com/
        In the UK? Hire me: http://www.sembee.co.uk/

        Sembee is a registered trademark, used here with permission.

        Comment


        • #5
          Re: Outlook Anywhere losing proxy settings, Autodiscover issue?

          Hi Simon,

          There is not autdiscovery record other than the SRV record. I have tried https://mail.pickardconstruction.com...todiscover.xml and it does not work. BelowV record taken right off Network Solutions:



          Is there a chance the cpanel autodiscover setting Outlook could be interferring? These clients are not members of the domain.

          Thanks
          Network Engineers do IT under the desk

          Comment


          • #6
            Re: Outlook Anywhere losing proxy settings, Autodiscover issue?

            That wasn't the URL I wanted you to test - it is the root of the domain.
            If you are getting an SSL warning - look at the certificate and see what it has been issued to. That will give you a pointer of where the error is coming from.

            Simon.
            --
            Simon Butler
            Exchange MVP

            Blog: http://blog.sembee.co.uk/
            More Exchange Content: http://exchange.sembee.info/
            Exchange Resources List: http://exbpa.com/
            In the UK? Hire me: http://www.sembee.co.uk/

            Sembee is a registered trademark, used here with permission.

            Comment

            Working...
            X