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How to connect Whonix Gateway to VB VPN Gateway?

How to configure Network Settings in Virtualbox Whonix Gateway to “take” internet connection from VPN Gateway made in another VB not from the host system?

host with VPN -> guest system in VB runing VPN -> Whonix Gateway -> Workstation

Is it possible?

Good day,

I’m not sure what you mean by this:

Are you saying you would like to have a Virtual machine and inside of that, host another Virtual machine with the Whonix Gateway? Because that’s impossible. Furthermore, you should ask yourself whether running this many VPNs is necessary and reasonable. Do you have access to two safe, top of the line, OpenVPN-based, not logging and anonymously payable VPNs, from two independent providers in countries, which are independent from the American, European or some other country’s legislation, which might force the company to log anyway?

Have a nice day,

Ego

i think he meant nested virtualization https://www.whonix.org/wiki/Nested_Virtualization

but i donno the answer if its possible or not.

Good day,

yes, but that is, as far as I can tell, currently only possible when using an Type-I-Hypervisor like Xen or KVM for the “host machine”, but not with VirtualBox, which is what the original poster seems to aim for, if the sentence “guest system in VB running VPN” is anything to go by. Using Qubes would pretty definitely be able to pull something of, however, I’m rather unsure, whether this would bring a security advantage, or rather actually be worse then running Whonix “normally” inside a Qubes VM, since no other host system is as good as Qubes when it comes to providing security through separation. So installing for example plain Debian or Fedora on to of Qubes, to then install a virtual machine in there, on which you run Whonix, might actually be less smart then simply installing Whonix the “classical” way on an AppVM in Qubes. For more information on how to install Whonix inside a Qubes AppVM, please read: https://www.whonix.org/wiki/Qubes

Have a nice day,

Ego

No, you completely misunderstood me.

Again, I was thinking about connecting Whonix Gateway through internal network connection (not NAT) to another VM that runs only VPN.

So it’s host system, then I’m opening VPN Gateway guest system (XP Pro), and THEN I’m opening second VM on the host system which is Whonix Gateway which connect ONLY with that VPN Gateway.

I can’t explain it clearer.

Good day,

Ok, that was a misunderstanding on my part, sorry for that. However, the question remains, wether you have two safe VPNs (since you wrote you want one on the Host as well) and what profit you would gain from such a construction. Because if you really live in a country, were the usage of TOR is something suspicious, one (really safe one) of them would be enough to hide the fact that you are connection to TOR. And, as far as I know, there is no other user case in which having a VPN before routing your traffic through TOR would be an advantage. And for that user case, you can actually simply add your VPN in the Whonix-Gateway by following this: https://www.whonix.org/wiki/Tunnel_Tor_through_proxy_or_VPN_or_SSH#VPN_on_Whonix-Gateway Furthermore, may I recommend using Debian or Fedora over Windows if you still want to use your “VPN-Gateway-Method”? It’s free and gets security updates.

Have a nice day,

Ego

Some theoretic info:

A VPN-Gateway that gets chained is possible in theory. Whonix-Gateway eth0 would have to be also just an internal network interface connected to another VM. Right, the whole thing gets easier with Qubes.

There is a Qubes article about this, but at time of writing, it contains a warning. https://www.qubes-os.org/doc/VPN/

Would be a lot development work to get the whole thing documented with VirtualBox. For Qubes, I don’t know how hard it would be to fix it.

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