Cannot connect to remote SQL Server over VPN, yet I can ping?

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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.

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Are TCP/IP connections enabled for SQL Server. Make sure these are enabled.

  • Start SQL Server Configuration Manager. Click Start, point to All Programs, and click Microsoft SQL Server. Click Configuration Tools, and then click SQL Server Configuration Manager.
  • In SQL Server Configuration Manager, in the console pane, expand SQL Server Network Configuration.
  • In the console pane, click Protocols for .
  • In the details pane, right-click TCP/IP, and then click Enable.
  • In the console pane, click SQL Server Services.
  • In the details pane, right-click SQL Server (), and then click Restart, to stop and restart the SQL Server service.