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I'm thinking about setting up a security testing lab. I work on a switched network, and that just makes for unnecessary headaches when doing testing.

I'd like to create a 192 network with a few machines inside for DBs and AppServers etc. I will need a pivot machine that connects to both the outer network and the 192 (for automation purposes). But I'd like to be able to connect into the 192 network with my own machine from the outer network as the "attacking" machine (rather than have dedicated attack machines inside the 192 network). Therefore, I'd like to have the pivot server be a VPN server as well, so that my machine can VPN into the 192 network from the outer network.

Is this even possible? Can I have a single computer with two NICs where a VPN service allows remote connections into the 192?


This is in an office environment. We're on a 10.x.x.x and while I'm sure there is an existing 192 somewhere, I'd like this to be entirely separate, as attacks may have unintended consequences elsewhere. This would be a pure addition to the existting network (likely on an ESX server).

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You're question is unclear. It sounds like you just need a router (real or virtual). As for VPN product suggestions, product suggestions are considered off-topic for SU. – Ƭᴇcʜιᴇ007 Aug 2 '13 at 15:45
Tell us more about your network. Are you in an office environment? Is any 192.168.X.X IP already in use? Are you able to replace or reconfigure the router for this network? – LawrenceC Aug 2 '13 at 16:24
I've removed the request for product help and added a bit more for @ultrasawblade. Let me know if this isn't enough info. I could draw a picture I bet... – tophersmith116 Aug 2 '13 at 17:27
up vote 2 down vote accepted

Well, you first need something running a VPN server, and a way to reach it from the outside.

If you have no way to configure your office's router to forward a port from the Internet to your system (and give you a fixed internal IP in the process), or ask someone to do this, then you'll need to run a VPN server (OpenVPN in particular) outside of the network, making sure client-to-client communication is enabled, and have a machine within your office that connects to it. You can then reach the system inside the network by connecting to the OpenVPN server.

You can use OpenVPN to join anything inside the network as well. If you have to put the server outside of the network, it will be inefficient as traffic will be going from your network, to the external VPN server, and back. You could set up a second OpenVPN server on the same machine as the first, one for inside your network and another outside.

You still have the issue of what range of IP addresses to choose. The best is if you can secure a range of unused IP addresses in your office's 10.x.x.x block - this will be simplest. If you have to reuse something already in use on your office's network, you'll need to set up NAT on the VPN server (or really should, rather).

Can I have a single computer with two NICs where a VPN service allows remote connections into the 192

Yes, and in this instance you'll need it. One NIC will be connected to your office network, the other will be connected to the systems you want to isolate on their own network. On this second NIC you'll need to attach a switch and connect all systems you want there behind it. You mention a "pivot" system in your question - the term you want to use for this is "router" - and, you will have to set up routing and DHCP on this system - Linux does routing (it's part of many consumer routers) and there are many DHCP packages for Linux. (I've used a PC with two NICs running Linux as a router for years.)

This is a bit of a high-level answer, and yes, it's involved (you are talking about needing to be familiar with Linux, OpenVPN, Linux's networking features, and setting up a DHCP server), but defintely possible.

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Looks like a busy week ahead for me! Thanks for your help – tophersmith116 Aug 5 '13 at 15:27

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