VPN within a Remote Desktop session

remote desktopvpn

I connect to a server on my local network via Remote Desktop. I then need to make a VPN connection out to the internet from within that Remote Desktop session. However that immediately disconnects my remote desktop session.

What's happening here and is there a way I can fix it?

Extra Information:

Local Computer #1:

  • Initiates RDP Session to #2
  • Windows 7
  • 10.1.1.140/24

Local Computer #2:

  • Windows Vista
  • 10.1.1.132/24
  • Initiates VPN connection to public IP
  • VPN is PPTP
  • Set to obtain IP and DNS automatically
  • 'Use Default Gateway on Remote network' is unselected
  • 'Enable LMHosts' is selected
  • 'Enable Netbios' over TCP/IP is selected
  • Has the ability to be multi-homed (ie. has 2 nic's)

Public facing ADSL Router:

  • VPN Server
  • receives connection from #2 via external IP
  • Internal network is 192.168.0.0/24

I can make a VPN connection from my PC with no problems (no RDP involved).

Tom suggested using dual NIC's in a comment below. I have dual NIC's in the box
(#2 above) but I'm not sure how to set them up properly, or how to assign the VPN to use one over the other.

I tried setting the extra NIC to be on the same private network (10.1.1.200/24), starting the VPN and then trying to RDP to either of the NIC's, 10.1.1.132 or 10.1.1.200 but didn't have any luck. Is there some way I can tell the VPN to use one NIC over the other?

As requested – here are my routing tables from PC#2:

Before VPN is connected:

IPv4 Route Table
===========================================================================
Active Routes:
Network Destination        Netmask          Gateway       Interface  Metric
          0.0.0.0          0.0.0.0       10.1.1.254       10.1.1.132     20
         10.1.1.0    255.255.255.0         On-link        10.1.1.132    276
       10.1.1.132  255.255.255.255         On-link        10.1.1.132    276
       10.1.1.255  255.255.255.255         On-link        10.1.1.132    276
        127.0.0.0        255.0.0.0         On-link         127.0.0.1    306
        127.0.0.1  255.255.255.255         On-link         127.0.0.1    306
  127.255.255.255  255.255.255.255         On-link         127.0.0.1    306
      169.254.0.0      255.255.0.0         On-link        10.1.1.132    296
  169.254.255.255  255.255.255.255         On-link        10.1.1.132    276
        224.0.0.0        240.0.0.0         On-link         127.0.0.1    306
        224.0.0.0        240.0.0.0         On-link        10.1.1.132    276
  255.255.255.255  255.255.255.255         On-link         127.0.0.1    306
  255.255.255.255  255.255.255.255         On-link        10.1.1.132    276
===========================================================================

and after VPN is connected:

IPv4 Route Table
===========================================================================
Active Routes:
Network Destination        Netmask          Gateway       Interface  Metric
          0.0.0.0          0.0.0.0       10.1.1.254       10.1.1.132     20
         10.1.1.0    255.255.255.0         On-link        10.1.1.132    276
       10.1.1.132  255.255.255.255         On-link        10.1.1.132    276
       10.1.1.255  255.255.255.255         On-link        10.1.1.132    276
        127.0.0.0        255.0.0.0         On-link         127.0.0.1    306
        127.0.0.1  255.255.255.255         On-link         127.0.0.1    306
  127.255.255.255  255.255.255.255         On-link         127.0.0.1    306
      169.254.0.0      255.255.0.0         On-link        10.1.1.132    296
  169.254.255.255  255.255.255.255         On-link        10.1.1.132    276
      192.168.0.0    255.255.255.0    192.168.0.254    192.168.0.234    267
    192.168.0.234  255.255.255.255         On-link     192.168.0.234    522
    remote-vpn-ip  255.255.255.255       10.1.1.254       10.1.1.132     21
        224.0.0.0        240.0.0.0         On-link         127.0.0.1    306
        224.0.0.0        240.0.0.0         On-link        10.1.1.132    276
  255.255.255.255  255.255.255.255         On-link         127.0.0.1    306
  255.255.255.255  255.255.255.255         On-link        10.1.1.132    276
  255.255.255.255  255.255.255.255         On-link     192.168.0.234    522
===========================================================================

I even tried hooking up the second interface (10.1.1.232) and playing with the default routes:

IPv4 Route Table
===========================================================================
Active Routes:
Network Destination        Netmask          Gateway       Interface  Metric
          0.0.0.0          0.0.0.0       10.1.1.254       10.1.1.132     21
         10.1.1.0    255.255.255.0       10.1.1.254       10.1.1.232     11
       10.1.1.132  255.255.255.255         On-link        10.1.1.132    276
       10.1.1.232  255.255.255.255         On-link        10.1.1.232    266
        127.0.0.0        255.0.0.0         On-link         127.0.0.1    306
        127.0.0.1  255.255.255.255         On-link         127.0.0.1    306
  127.255.255.255  255.255.255.255         On-link         127.0.0.1    306
      169.254.0.0      255.255.0.0         On-link        10.1.1.132    296
  169.254.255.255  255.255.255.255         On-link        10.1.1.132    276
      192.168.0.0    255.255.255.0    192.168.0.254    192.168.0.235    267
    192.168.0.235  255.255.255.255         On-link     192.168.0.235    522
    remote-vpn-ip  255.255.255.255       10.1.1.254       10.1.1.132     21
        224.0.0.0        240.0.0.0         On-link         127.0.0.1    306
        224.0.0.0        240.0.0.0         On-link        10.1.1.132    276
        224.0.0.0        240.0.0.0         On-link        10.1.1.232    266
  255.255.255.255  255.255.255.255         On-link         127.0.0.1    306
  255.255.255.255  255.255.255.255         On-link        10.1.1.132    276
  255.255.255.255  255.255.255.255         On-link        10.1.1.232    266
  255.255.255.255  255.255.255.255         On-link     192.168.0.235    522

Best Answer

What's happening is that you're effectively cutting off the IP route from the server to yourself - hence the RDP session loss. You can fix it by setting up the VPN in a way that it's bound to a second interface (physical or virtual) so that both the VPN and RDP link can coexist. How you do this depends enormously on a range of very detailed configurations that we don't know right now, so if you want help with this you'll have to come back to us with a LOT more information, just as much as you can please.