My VPN appears to be working, since without it I cannot ping the server. When I establish VPN connection I am able to both ping and Remote into the virtual server but cannot connect, getting this message:
Connection Timeout Expired. The timeout period elapsed while attempting to consume the pre-login handshake acknowledgement. This could be because the pre-login handshake failed or the server was unable to respond back in time. The duration spent while attempting to connect to this server was - [Pre-Login] initialization=18193; handshake=14371; (Microsoft SQL Server, Error: -2)
The curious thing about this is I am able to connect on my old machine using the same VPN software, on the same network.
Are TCP/IP connections enabled for SQL Server. Make sure these are enabled.