I have recently installed our first and only Exchange 2007 server in our Domain. All server roles are on one machine. Mail flows perfectly. Outlook 2007 autodiscover works perfectly inside of our network as well. Unfortunately, when I attempt to connect Outlook 2007 outside of our network with autodiscovery, I am prompted for a user name and password, repeatedly andendlessly. Here are some notes: 1. All Exchange websites are hosted in the default manner. 2. We have two simple external DNS host records: mail.funa.com and autodiscover.funa.com, both of which point to our single external IP address. 3. I have purchased and installed a godaddy wildcard certificate on the IIS server. It appears in all of the websites. 4.Outlook Web Access works without any certificate errors both inside and outside of our network. 5. If I configure Outlook 2007 to use RPC over HTTPS manually when outside of our network, it works. 6.Testing Outlook autodiscovery with the connection tool reveals no errors. It appears to me that Outlook 2007, when outside the network, will not seek the RPC over HTTPs route with Autodiscovery. Is that the case?