Question : Prompted for Remote.Domain.com password in Outlook 2007 small business

Server configuration;
SBS 2008, Exchange 2007, Rollout 9 installed
Workstations configuration;
Windows XP SP3 Office 2007 Small Business
When opening outlook getting prompted for 2 user name passwords, 1st is for actual mail from the SBS server, the other is for Remote.domain.com site. Entering windows long info in the non remote.domain.com authentication resolves its need unless u reboot etc etc. As for the remote.Domain.com no password works, and needs canceling twice ever 20 minutes or so. Unacceptiable, can someone advise a possible scenario to resolve this issue, Cheers

Answer : Prompted for Remote.Domain.com password in Outlook 2007 small business

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