Including multiple machines on the client side when using a routed VPN (dev tun)
 
In a typical road-warrior or remote access scenario, the client machine connects to the VPN as a single machine. But suppose the client machine is a gateway for a local LAN (such as a home office), and you would like each machine on the client LAN to be able to route through the VPN.
 
For this example, we will assume that the client LAN is using the 192.168.4.0/24 subnet, and that the VPN client is using a certificate with a common name of client2. Our goal is to set up the VPN so that any machine on the client LAN can communicate with any machine on the server LAN through the VPN.
 
Before setup, there are some basic prerequisites which must be followed:
 
The client LAN subnet (192.168.4.0/24 in our example) must not be exported to the VPN by the server or any other client sites which are using the same subnet. Every subnet which is joined to the VPN via routing must be unique.
The client must have a unique Common Name in its certificate ("client2" in our example), and the duplicate-cn flag must not be used in the OpenVPN server configuration file.
First, make sure that IP and TUN/TAP forwarding is enabled on the client machine.
 
Next, we will deal with the necessary configuration changes on the server side. If the server configuration file does not currently reference a client configuration directory, add one now:
 

 
In the above directive, ccd should be the name of a directory which has been pre-created in the default directory where the OpenVPN server daemon runs. On Linux this tends to be /etc/openvpn and on Windows it is usually \Program Files\OpenVPN\config. When a new client connects to the OpenVPN server, the daemon will check this directory for a file which matches the common name of the connecting client. If a matching file is found, it will be read and processed for additional configuration file directives to be applied to the named client.
 
The next step is to create a file called client2 in the ccd directory. This file should contain the line:
 

 
This will tell the OpenVPN server that the 192.168.4.0/24 subnet should be routed to client2.
 
Next, add the following line to the main server config file (not the ccd/client2 file):

 
Why the redundant route and iroute statements, you might ask? The reason is that route controls the routing from the kernel to the OpenVPN server (via the TUN interface) while iroute controls the routing from the OpenVPN server to the remote clients. Both are necessary.
 
Next, ask yourself if you would like to allow network traffic between client2's subnet (192.168.4.0/24) and other clients of the OpenVPN server. If so, add the following to the server config file.
 
client-to-client
push "route 192.168.4.0 255.255.255.0"
This will cause the OpenVPN server to advertise client2's subnet to other connecting clients.
 
The last step, and one that is often forgotten, is to add a route to the server's LAN gateway which directs 192.168.4.0/24 to the OpenVPN server box (you won't need this if the OpenVPN server box is the gateway for the server LAN). Suppose you were missing this step and you tried to ping a machine (not the OpenVPN server itself) on the server LAN from 192.168.4.8? The outgoing ping would probably reach the machine, but then it wouldn't know how to route the ping reply, because it would have no idea how to reach 192.168.4.0/24. The rule of thumb to use is that when routing entire LANs through the VPN (when the VPN server is not the same machine as the LAN gateway), make sure that the gateway for the LAN routes all VPN subnets to the VPN server machine.
 
Similarly, if the client machine running OpenVPN is not also the gateway for the client LAN, then the gateway for the client LAN must have a route which directs all subnets which should be reachable through the VPN to the OpenVPN client machine.