Static Route over VPN

DrDamnit used Ask the Experts™
I have a box to box vpn setup between two offices.

In office T, the network is In office A, the network is The box to box VPN and static route from A to T works great. I can ping any machine on either network.

THere is a wrinkle here though... Box A's gateway is THey have a Comcast Cable service. So, the WAN interface of the firewall that is doing the box to box VPN (m0n0wall) is plugged into a comcast gateway. From the network, we can access the comcast box by typing It works. From the T network, it doesn't.

I tried setting up a static route from -> Gateway( ->, but the local gateway (T) just tells me that is not reachable (message originates from, the gateway in office T).

How should I be setting up this static route?
Watch Question

Do more with

Expert Office
EXPERT OFFICE® is a registered trademark of EXPERTS EXCHANGE®
It sounds like you want all traffic to go out office A's gateway?  You'll probably need another box as most gateways don't like to do U turns in the box (coming in the WAN over the VPN and reversing right back out to the WAN for the Internet).  

If it's just web browser traffic you are wanting to take that path, an easy way is to put in a proxy in Office A and have Office T use that proxy for their web traffic.

Do I understand the problem correctly?
Qlemo"Batchelor", Developer and EE Topic Advisor
Top Expert 2015
Did you set up that static route on gateway in T? That (and only that) should work, if the U-turn is ok for the A gateway. That is a valid point - in particular Cisco routers (PIX) are known for this (they do not allow U-turns aka "hair-pinning").
Most Valuable Expert 2012


no hair-pinning allowed seems to be it.

Do more with

Expert Office
Submit tech questions to Ask the Experts™ at any time to receive solutions, advice, and new ideas from leading industry professionals.

Start 7-Day Free Trial