We just setup a new Windows Small Business Server 2008 with Exchange 2007 (with sp3 and all the rollups) and configured Outlook anywhere. Outlook anywhere doesn't seem to work from outside the network and only works inside the network when both the server in the Outlook config setup and the URL for the proxy server are set to SERVERNAME.DOMAIN.local (both http and https work inside the network). If I set it to SERVERNAME.DOMAIN.com (which would be the same externally) it connects but it asks for a username/password and no matter how it is entered it doesn't validate (DOMAIN\username, DOMAIN.local\username, etc). Any ideas on what to try next?
Also I should mention that Outlook web access works fine too.