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I've just configured SQL Server 2008 R2 Express on Server 2008 R2, with the idea to administrate it remotely via the Routing and Remote Access VPN.

Everything is fine via the VPN and the connection works, however, the service fails to start following a restart of the system because its listening to an IP address that isn't in existence until the VPN is connected, which isn't ideal.

Is there any way to prime the IP prior to the first VPN connection, or any other way around?

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You would need to statically assign an IP address on the server that is in the same subnet as what your VPN connection is on. But that's not what I'd recommend.

The networking should really be fixed so that the subnet you're using for VPN can talk to an internal subnet the SQL box already knows about. Then change SQL to listen bind to an address in that internal subnet.

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