Trying to connect a new install of Outlook 2013 to an Exchange 2010 server over VPN. As soon as a new profile is set up and click on "Check name" immediately get "The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action."
This is a machine outside of the office and not on the domain. Can ping the server by name, can connect with Outlook 2003 or 2010 without an issue. Do not have a 3rd party SSL certificate.