Question : Outlook 2007 keeps asking for credentials for remote connection to server

Having this excact problem (which is solved for SBS2008 SP1):
http://www.experts-exchange.com/OS/Microsoft_Operating_Systems/Server/SBS_Small_Business_Server/Q_24989899.html
and:
http://www.thirdtier.net/2009/12/outlook-repeatedly-prompting-for-authentication/

My customer has the same problem though on a fresh installation of SBS 2008 SP2, so I can't see the cure in this case.

Any help is greatly appreciated.

Answer : Outlook 2007 keeps asking for credentials for remote connection to server

Have you got a UCC/SAN certificate installed? If so does it have the record autodiscover.domainname.com in it?

Also do you have an A recors in your external DNS for autodiscover.domainname.com it should be pointing to the same IP as your Outlook Web Access URL.

For the second prompt you can try the above.
I have had mixed comments some say the first work and some say the second work but the second one seems to be winning at the moment:

http://social.technet.microsoft.com/Forums/en/exchangesvrgeneral/thread/383d130e-869f-4fce-9502-8b340904b0ba


See the section about enabling Kernel Authentication: http://social.technet.microsoft.com/Forums/en-US/exchangesvradmin/thread/0c94187d-bc97-4fa5-9413-e8762a25a360