OpenVPN Support Forum

I have a setup with 1 OpenVPN Server and multiple Clients.

Server-Site 192.168.1.0 255.255.255.0
Server VPN IP 192.168.1.50 (VPN IP 10.8.8.1)

ClientX-Site 192.168.50.0 255.255.255.0
Client IP 192.168.50.50 (VPN IP 10.8.8.2)
Client Extra IP 192.168.50.150

I would like to be able to ping/connect from Server IP (192.168.1.50) to Client Extra IP (192.168.50.150) on ClientX-Site using Client IP (192.168.50.50) which is connected using OpenVPN.

I've added some routing so...
- Client IP can ping everything on Server-Site
- Server IP can ping Client IP
- Server IP can NOT ping Client Extra IP
- Client Extra IP can NOT ping Client IP when Client IP is connected to VPN

Any thoughts?

On the Client IP I ran following command:
iptables -t nat -A POSTROUTING -s 10.8.8.0/24 -o eth0 -j MASQUERADE

Now I can ping Client Extra IP from Server VPN IP!

Last thing I would like to get to work is to be able to ping from a secondary client on Server-Site to Client Extra IP. Any thoughts?

you need add iroute into server config so it know how to route to client subnet.. what you should looking is site to site connection . you are nearly done just make a little bit . it will work for you.