Outlook will not configure (manually or using autodiscover) for the first time from the outside network. I have tried both Outlook 2007 and Outlook 2003 and after Outlook prompts me for the server credentials I receive:
"This action cannot be completed. The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action"
I have installed and configured a new Windows 2008 x64 server with Exchange 2007 sp1, with a Verisign SAN certificate containing the netbios name, mail.mydomain.org, and autodiscover.mydomain.org. All updates have been installed. The server is behind an ASA5505.
OWA works great both internally and externally, I have configured the Exchange 2007 Autodiscovery settings so that autodiscover works when you are on the internal network. It configures Outlook 2007automatically and then RPC over http(Outlook Anywhere) works even when you connect from the outside network. Once configured it works great. I can work around this but it is bugging me. I have configured the VPN client on the ASA so I can connect via VPN configure outlook then disconnect and all is good