Outlook autodiscover popup issue - SBS 2008/Exchange 2007

Posted on 2010-01-07
Last Modified: 2012-05-08
Ok, here we go..  The main problem is my outlook clients are getting username/password popups constantly.  I have created, bought, and installed a UCC via exchange management shell for,, and myserver.mydomain.local

1)  I am under the impression that it is an autodiscover issue, and I use the following commands to update the autodiscover properties:

Set-ClientAccessServer -Identity CAS1 -AutodiscoverServiceInternalUri

Set-WebServicesVirtualDirectory -Identity CAS1\EWS (Default Web Site) -InternalUrl

Set-OABVirtualDirectory -Identity CAS1\oab (Default Web Site) -InternalUrl

Set-UMVirtualDirectory -Identity CAS1\unifiedmessaging (Default Web Site) -InternalUrl

The first command entered successfully, the last 3 errors out saying "default web site could not be found on domain controller"

2)  I have also been told to go in IIS on the Exchange server.  (since it is SBS its all the same server)  Under Autodiscover properties> Directory Security> Authentication Methods> check "Integrated Windows Authentication".

well, I cant seem to find the autodiscover virtual server to view the properties.

 I hope this makes some sort of sense, please feel free to ask any questions you need to help me sort this out.
Question by:bensc2367
    LVL 76

    Accepted Solution

    Exchange 2007 Service Pack 1 Rollup 9 should solve your username / password popup issue.  Please download and install it:
    LVL 15

    Expert Comment

    If you already have rollup 9 or above check these.

    In SBS 2008 Exchange virtual directories are under SBS Web Application

    Change the command
    Set-WebServicesVirtualDirectory -Identity CAS1\EWS (SBS Web Application) -InternalUrl

    Note: SBS Web Application is case sensitive check in IIS and then type.

    The Domain name ( Url that you are specifying should be in SAN certificate and you should be able to resolve it to the CAS server Can you ?

    Check these Authentication types for virtual directories as well:

    IIS >SBS Web Application

    SBS Web Application Should have annonymous and no SSL
    1) Autodiscover: Basic and Integrated authentication SSLOptional
    2) EWS : Integrated authentication NO SSL
    3) Exadmin : Basic and Integrated authentication NO SSL
    4) Exchange : Basic and Integrated authentication SSL optional
    5) Exchweb : Basic and Integrated authentication NO SSL
    6) Microsoft-Server-ActiveSync: Basic authentication SSLOptional
    7) OAB : Integrated authentication NO SSL
    8) OWA : Basic authentication SSL Optional
    9) Public : Basic and Integrated authentication SSL Optional

    Author Closing Comment

    Thank you very much, I have been going crazy with this for a week or 2 now - so glad it was a quick fix.  Cheers

    Author Comment

    Thanks to both of you, I awarded points to alan because that fixed the specific issue i was having.  BTW I had to run the update rollup as administrator via command line in order for it to install properly.  I followed these guidelines -

    Sing that is also very helpful and should help me with the errors i'm getting on the other 3 commands.  cheers to you both

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