At what point does it "bomb"
When authenticating, on page with server name and authentication information.
how are you attempting to deploy it? Are you using the DatabaseMigrator class or deploying through the DDT?
Using the deploy database wizard directly in the DDT
Also, what type of connection is this?
I have access to port 1433 and terminal services on port 3389.
If there is a VPN then there should be no issue, but if these are just exposed ports then there could be some issue there in the connection.
Whenever I connect to the db, I have to indicate the network library to use and also use the IP. This is how I connected to it within SQL Server Management Studio.