I am tearing my hair out after performing a Windows update on the SBS2008 box. Now all Outlook 2007 clients keep popping up the username/password box every 2 minutes. Outlook 2003 are unaffected.
I've been researching this for hours (including reading all the similar tickets here) and it seems to be related to an autodiscover issue. Outlook clients (within the LAN) when doing "Test Email Autoconfiguration..." simply say "autoconfiguration was unable to determine your settings" - thats it. Nothing else appears. No attempts to reach https://server.domain/autodiscover/autodiscover.xml
To try and fix this issue I have:
Updated the server's self signed certificate so the servers address (45maplest.blah.com.au) is exactly the same as what you use to access it from outside.
Updated the DNS (DNS is external managed by the email host) so 45maplest.blah.com.au points to the servers public IP address. Internal DNS on the SBS2008 box was automaitcally set up with 45maplest.blah.com.au as part of the internet address wizard.
Turned off "Connect to Exchange using HTTP" on the Outlook clients on the internal LAN. The issue remains whether this is used or not
Imported the SBS2008 certificate via the Public Downloads section and also via IE connecting to https://45maplest.blah.com.au
When doing https://server.domain/autodiscover/autodiscover.xml
from IE the authentication box pops up again. Putting in a users credentials also keeps popping up the logon box until eventually it says you do not have permission to view this directory or page.
When i look in internal DNS on the SBS box there is no record relating to autodiscover. Is this normal? I have checked another SBS2008 install which does not have the issue and it also doesnt have autodiscover listed in internal DNS on SBS2008 so i suspect thats ok.
I think my first aim is to get the Test Email Autoconfiguration working so at least it can run the test. Can anyone help? This is pretty critical.