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etaketa: If you look at my post you will see that I am NOT using the same interface and therefore hairpinning can not be the issues.

Why go through the effort when this configuration should work ?

I don't doubt that it will work however, it does not provide the solution within the Microsoft framework. I know there is a straight forward solution to this very common multi-homed VPN server configuration.

VPN GURU CHALLENGE is in order here. I have the same exact issue and have struggled with it for a year. IF I add a static route on the VPN server that captures 0.0.0.0/0.0.0.0 and sends to our hardware based Internet router gateway address, Internet access works for a while but then the VPN...

I separate Internet access firewalling from VPN firewalling so I don't think my packets are going out and in the same interface. We have a separate firewall and IP address for the external interface on my VPN Server. Once the VPN client establishes a connection with the VPN Server, it should be...

VPN GURU CHALLENGE is in order here. I have the same exact issue and have struggled with it for a year. IF I add a static route on the VPN server that captures 0.0.0.0/0.0.0.0 and sends to our hardware based Internet router gateway address, Internet access works for a while but then the VPN...