We have an EC2 Windows 2008 server and 3 servers hosted at Rackspace (also windows 08). I would like to be able to address the EC2 server as though it were part of our internal Rackspace network. Thus I'm thinking that we should be able to use a VPN or some sort of tunneling technology to allow this.

Does anyone have any experience or any suggestions on how to do this?

We need to run executables that access various services on our internal boxes, (DB, MongoDB, nCache caching service, and others).

I'm trying to avoid rewriting the .exe to throw everything through a web service.

Thnks for any help,


Use openvpn http://openvpn.net/

You can setup the tunnel to go either direction, use passwords or certificates, windows or linux, goes over whatever port you want, etc. Very simple, very secure.

You'll need to open up a port on a firewall at one of the sites to accept the incoming connection, so the direction that's of the least administrative effort (amazon->rackspace) or (rackspace->amazon) is up to you.


Whilst OpenVPN is the cheapest way in sense of money (and I'd take it too), you may be not comfortable with it if you're not a tech savvy person. Also, if you have many Rackspace servers then you'll have to set up OpenVPN on each of them or configure one server as a gate/router to let ec2 reach other RS instances.

So the alternative, "the lazy way": Ask Rackspace to configure VPN fot servers on that side. They will configure firewall on their side for you if needed. The only part you'll have to do - configure VPN client on the EC2, but RS have pretty straightforward instructions how to connect their VPN form an external Windows box, thus it shouldn't be a problem.

Every time EC2 boots up, it should connect to VPN and you're done.

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