I have a SBS 2008 server and everything is running fine except for Outlook Anywhere…
OA was working fine and nothing has been installed but in the last week it is working sporadically. OA is enabled through the Exchange Management Console, the RPC proxy is installed and running, my certificates are up to date and all the necessary services are running but my Outlook clients are in a perpetual state of “Trying to connect.”
My firewall has SSL ports open and forwarded, I can get to the SBS Remote pages and do things like view the company website, use OWA and RDP into a desktop just fine as well.
Additionally, I’m using Basic Authentication and the Outlook clients are configured for the internal FQDN server.domain.local with the msstd:externalsubdomain.domain.com.