Question

Can't ping from devices behind the VPN to devices connecting to VPN

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Hello, I have set it all up following the instructions, my MacBook connects to the OpenVPN server gets an IP etc and I can ping the server that is behind in the network that the OpenVPN server sits on. That is all good.

So the OpenVPN server is 10.0.0.5 and I have a Domain Controller on 10.0.0.4 and it can ping .5 no worries.

My VPN connected device 10.8.0.2 can ping 10.0.0.4 no problems! But 10.0.0.4 cannot ping 10.8.0.2! I feel like there is some reverse routing or something that we are missing?

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You have to uncomment the ‘client-to-client’ portion in the /etc/openvpn/server.conf file to let the clients ping and ‘see’ each other.

The easiest way to get traffic flowing would be to configure the system at 10.0.0.4 to also have a VPN connection.

Otherwise, you’ll need to add a route for the VPN subnet on the 10.0.0.4 system to send traffic via the VPN server.

Assuming the subnet is something like 10.8.0.0/24, you’d add a route like ths on the 10.0.0.4 system:

sudo ip route add 10.8.0.0/24 via 10.0.0.5

That will at least get traffic onto the VPN server and you can then troubleshoot how it is flowing from there.