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I have two sites I currently look after. The first uses subnet 192.168.30.x and houses our Open VPN server and the other site is on 192.168.31.x.

If we VPN in we get an IP of 192.168.30.x. But when attempting to RDP to a machine at the remote site 192.168.31.x the connection can't be made. We have the VPN between sites set up so the RDP session to the machines works from site 192.168.30.x when not on VPN.

I'm guessing this is a routing issue and a setting needs to be made to router 192.168.31.x to allow connection over VPN? But not sure what.

Both routers at both sites are Draytek Vigor.

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  • When you VPN into the first site is your client's default gateway pointing to the router at the first site? The client sends any traffic that isn't on the local subnet (i.e. the 192.168.30.0 subnet) to the default gateway (router) which in turn forwards it to the correct destination network. Dec 28, 2016 at 20:55

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Why type of VPN did you setup? Is it a true site-to-site VPN?

First I would test to see if you can communicate at all with the other subnet. For example, when connected to the .30 subnet try pinging any devices on the .31 subnet. If you cannot ping anything then it is a routing issue and you'll need to either set a policy in your firewall/router or configure the VPN to allow that traffic.

For example on my Watchguard firewall I am able to connect using a VPN with a different subnet, but in the VPN settings I have it set to allow the use of resources on the main LAN.

I have another customer with a site-to-site VPN setup using two Watchguard, but again the policy allows all traffic through so I can ping and access any devices at each location.

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  • Thanks MindExplosion I have ip sec set up between the 2 sites and can ping devices from both sites fine and the rdp connection works It's just purely once connected remotely via the open vpn client the rdp session then fails
    – Matthewr
    Dec 21, 2016 at 19:51
  • Sorry for the late response as it's been a hectic Christmas! So to clarify you have a VPN setup between both sites that works fine? So if you're onsite at the .30 network you can in fact RDP into the .31 subnet? It's only once youre offsite and using Open VPN to connect in, that you cannot RDP over? Dec 27, 2016 at 23:54

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