Why can’t I control a Windows PC using Remote Desktop when connecting to it over VPN?

August 21, 2014 at 03:06PM:

We need help with Remote Desktop over VPN. It fails when the target machine connects to an external network.

We have a Windows 7 machine on our LAN configured to accept remote desktop connections. That machine can also connect to a remote server via a VPN (VPN1).

When the client machine is on the physical LAN, it connects to the target machine, regardless of whether the target machine has a connection to VPN1. However, when the client machine is off the physical LAN and connected to it via VPN2, it can only connect to the target machine if the connection to VPN1 is not active.

I checked the port usage and VPN1 is not trying to take control of the RDC listening port. The IP addresses of these networks are all distinct, on separate domains:

LAN: 192.168.0.x

VPN1: 10.19.125.x (target RDC machine -> remote server)

VPN2: 192.168.2.x (client RDC machine -> LAN)

Does anyone have any ideas what might be going wrong? VPN1 is pptp and VPN2 is ipsec.

Thanks for any suggestions!

David

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