Step by step guide on OpenVPN and VirtualBox server config

lolex

Hi all,

During several days I've been searching for tutorials on how to setup OpenVPN with a virtual machine but none of them match the specific situation I want to setup. I've tried their config and steps but always end with an SSL error. The client doesn't even connect I think. Do you know of a step by step guide for the particular situation I'm going to explain next?

What I want to do is configure two virtual machines on my win7 host (already done). One with WinXP which will be a OpenVPN client and another with Linux Mint (based on Ubuntu) as a server.

The win7 host will connect to an external OpenVPN server based in Romania. The winXP will connect to the internal OpenVPN server (the Linux Mint OS) so inside winXP it will appear as if I'm in Romania plus all the traffic from the winXP OS will appear as encrypted to the external Romanian OpenVPN server.

The reason I want to do this is that there are rumors about the external free OpenVPN server in Romania being monitored by the feds when I did a search on it. One of the commenters said that a solution to this situation is to make an internal tunnel similar to what I described.

Here's is a diagram to better understand the config I want to make:

lolex

No one knows how? :cry:

mwandelaar

lolex wroteThe reason I want to do this is that there are rumors about the external free OpenVPN server in Romania being monitored by the feds when I did a search on it. One of the commenters said that a solution to this situation is to make an internal tunnel similar to what I described.

I might not understand your problem correctly, but if the virtual WinXP client sents al it's traffic to the virtual-Mint-vpn-server, it decrypted by the virtual Mint-server and handed in clear text to the Win7-VPN-machine.
There it's encrypted again (still once crypted!) and sent to your Romain VPN-server, which decrypts this and sents it in plain to the internet.

This adds no security whatsoever to your entire system, as to the outer world it seems like you are surfing the web with an WinXP machine. And the feds can still monitor the Romanian VPN-server, just as you can yourself on the Win7 machine.

What's the real problem/thread you are trying to solve/mitigate?

lolex

Hi mwandelaar, thanks for your interest,

My objective is that all traffic that comes from my computer and is received by the Romanian VPN server is completely encrypted and can't be monitored or decrypted by them.

mwandelaar

All the traffic between the Windows 7 client and the Romanian VPN-server is allready encrypted, unless you turned it off on purpose.

Having said that, if you are redirecting all your internettraffic via the romanian server and somebody can monitor that server, they can still see your internet-traffic unencrypted, as it leaves the vpn over there for the journey into the worldwide web.

Hope this helps.