I have recently installed an SBS 2008 Server. I followed the install to the letter, purchased a cert and installed it. The certificate seems to work correctly when hitting the box from outside the network. When attaching an Outlook client inside the network however Outlook 2007 prompts for credentials and is referencing the external URL. I have created an A record in DNS called autodiscover and am pointing it to the file server IP address. No luck. Its a single server, flat network with 40 seats so shouldn't be too complicated. Your help is appreciated.