RDP -> Gateway -> VPN -> Corporate

One of the frustrating things about VPN is that it kills active RDP sessions on the client once the VPN connection is established.  Sure, this isn’t the typical approach in the use of VPN and RDP, but in my case I wanted to RDP to a single machine at home that itself has a VPN connection to a secured network.  I found the answer on Google Groups, and decided to repost here for my own reference:

The scenario is as follows:

 Home Computer –> RDP Office Computer
 Office Computer –> VPN –> Corporate Headquarters

 XP pro is running on both home and office computer.

 Office Computer is a stand-alone computer.  (No Domain Controller; Static IP
 on Broadband Connection)

 Connecting through RDP to Office works fine.

 From office computer VPN connection to Corporate works fine from the office.

 What is trying to be achieved is having VPN connect once an RDP session is
 Home Computer –> RDP Office Computer –> VPN –> Corporate Headquarters

Solution is straight forward for those wanting to know.

On the office Machine to be connected via VPN to the corporate Network:

Create a VPN connection to the corporate network.  Under the properties for
this connection, select the General tab.  Select TCP/IP properties; Select
advanced options.  Under the General tab remove the check mark in front of
“Use Default Gateway on Remote Network.”

This will allow for the VPN connection to be established without crashing
the session.  One can now run scripts mapping network drives.  

For applications needing to connect to a server one final step needs to be
completed and that is modification of the Host file.  In this case there were
two servers I needed to connect to; Exchange and a Corporate Database.  In
the host file I entered the server FQDN and IP address.

3 thoughts on “RDP -> Gateway -> VPN -> Corporate

  1. Chas Bickford

    This unfortunately does not work for me.
    I am RDP into Windows 2003 SBS server and vpn to multiple other servers.
    RDP session lost from client but server has vpn up and running.
    Remote gateway ticked!!

  2. hose

    We use a <a href=”http://world-secure-channel.com/why/”>vpn</a> to secure connectivity – this eliminates the need to expose internal systems to the whole wide world. Related to topic- <a href=”http://vpnomania.com/proxy-surf.html/”>proxy</a>

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