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Suggestions on running a VPN in front of a Terminal Services server

Posted on 2012-03-30
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Last Modified: 2012-04-05
We're working with a subsidiary company that runs a Windows 2003 Server in Terminal Services mode to allow employees to work from home.  The same machine is also used to allow other subsidiaries on different network segments to remote in to the server.  The parent company has requested that all external traffic in to the TS Server now be across a VPN.  What is the quickest, cheapest way to accomplish this while making it as easy as we can on the employees who want to work from home and leaving internal employee traffic in to the server untouched?  In our opinion, RDP is already secure and that makes the requirement more of a line item to cross off rather than a major security project.  Any advice or EE links will be greatly appreciated.  Thanks,
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Question by:james_axton
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by:ldelgado2323
ldelgado2323 earned 150 total points
ID: 37788873
Do you have any sort of firewall in place? if so, we can implement several solutions for this requirement, also, do you have a domain controller in place, this way we can use the security settings to create a VPN connection through routing and remote access......
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by:james_axton
ID: 37789081
There is both a hardware firewall and a DC.
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by:adamnl
ID: 37793063
Are you sure about the statement 'RDP is already secure'? http://nakedsecurity.sophos.com/2012/03/16/rdp-exploit-china/

As a security consultant, I would give the same advice to clients. How to configure the VPN depends on the solution of your choice. As mentioned before the DC can be used to validate login credentials. For added security use certificates on company laptops (so people cannot easily connect with their insecure and possibly virus infected home pc).
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by:james_axton
ID: 37797452
Let's close this out.  We can run this through an existing firewall (presumably with some sort of licensing, unless that ability was included) or we can purchase a hardware VPN.  What are the other options here?  idelga, please followup with any suggestions you might have, and adamnl please do the same.  Thanks,
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Expert Comment

by:ldelgado2323
ID: 37797460
If you give me the Firewall model, I can suggest some ways to do this if you still need help...
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adamnl earned 350 total points
ID: 37797555
There are two approaches to using a firewall with a VPN server:

* VPN server in front of the firewall. The VPN server is attached to the Internet, and the firewall is between the VPN server and the intranet.

* VPN server behind the firewall. The firewall is attached to the Internet, and the VPN server is between the firewall and the intranet.

I advice the latter; the firewall is attached to the Internet, and the VPN server is an intranet resource that is attached to the Perimeter Network. The VPN server has an interface on both the perimeter network and the intranet. In this scenario, the firewall must be configured with input and output filters on its Internet interface that allow tunnel maintenance traffic and tunneled data to pass to the VPN server (For an additional layer of security, the VPN server can also be configured with PPTP or L2TP/IPSec packet filters on its perimeter network interface).

Because the firewall does not have the encryption keys for each VPN connection, it can filter only on the plaintext headers of the tunneled data. In other words, all tunneled data passes through the firewall. This is not a security concern, however, because the VPN connection requires an authentication process that prevents unauthorized access beyond the VPN server.

Settings that are set in this setup can be found here: http://technet.microsoft.com/en-us/library/cc737500%28v=WS.10%29.aspx#sectionSection3
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by:james_axton
ID: 37813761
Thanks to everyone for the input!
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