No, I Will Not Fix Your #@$!! Computer → Manully specifying route hop

Because of the lack of sleep and the amount of effort getting this remote site online, I'm missing a basic routing step somewhere along the line.
*External IPs listed are fictitious.

Gateway A - IP address 192.168.8.1
IP address alias 10.0.8.1
Gateway B - IP address 192.168.12.1

Gateway B dials into Gateway A. A link is established via VPN and data flows without issue. Attempting to connect to server 10.0.8.11 from computer 192.168.12.10 gets routed to the Internet.

I'm manually specifying a route on Gateway B to route the data to Gateway A but the traffic isn't hoping correctly.

What would I need to specify for the next hop?

What is the vpn on? You need to add a route that tells the device anything with destination 10.0.8.0 needs to use the vpn tunnel and not the default gateway. Which you probably know. Is it cisco, pfsense with openvpn, or something else?

OpenVPN. I think that is where I'm screwing up. Derrr. It would make sense since it is sending the data out to the next hop (router's gateway and not the VPN). Checking on it now.

Thanks boognish . Your suggestion pushed me in the correct direction. I had to export the network with OpenVPN which, after doing so, configured the route.

»wiki.untangle.com/index. ··· Networks

I'm using openvpn on my home NAS, and I connect to it whenever I'm somewhere with open wifi - this way, all my traffic is encrypted.

What I did was put the following in my openvpn.conf:

push "route 172.16.10.0 255.255.255.0"
 

that advertises the route via the VPN tunnel to 172.16.10.0/24.

Then, in my ccd file (client-specific config):

push "redirect-gateway def1"
 

That tells the client to redirect ALL of their traffic through the tunnel. That's what I want when traveling.

OpenVPN rocks. :)

You can actually do that from the server end as well. I use OpenVPN on my router, with Tomato firmware. I just have to check the boxes for Direct clients to redirect internet traffic, Respond to DNS, and Advertise DNS to clients. Now the server tells my client to send everything through the tunnel.

And agreed, OpenVPN Rocks!

Correctamundo - I put those statements on the server side openvpn.conf - not in the client (that's why there's a push statement.)

I don't have fancy checkboxes since I'm running it all on my Synology device, but it's still awesome.