Whonix VM & VPN Modem

VirtualBox
1

From reading “Combining Tunnels with Tor” page I do get the sense VPN usage is not an optimal scenario.

However, I would like to verify if my setup matches any of the combinations discussed regarding Tor and VPN setup.

I do run Whonix on a KVM, host machine is Debian Kicksecure.
The PC, Debian Kicksecure, is connected to a physical pfsense firewal (PC)l that is setup with VPN and this pfsense PC connects to the ISP’s modem.

So, the VPN setup is not within Whonix setup, nor on the host OS.

Am I running any of the risks that are mentioned in the “Combining Tunnels with Tor” page, like:

  • “If other things are done over the VPN connection like SSH traffic, IRC traffic, SMTP or OS updates, all of this traffic is sitting right next to each other.” ?

What category, form the examples in the “Combining Tunnels with Tor” page my setup falls under? Or the page only addresses inside setup within Whonix either Gateway, Workstation, or both?

Would it be safer to just connect the host Debian Kicksecure directly to the ISP’s modem while using Whonix VM?

How I am visualizing it with my setup, and I could be wrong, is a double assurance regarding any IP leak; that is, if Whonix leaked my IP, VPN is another layer to protect against IP leak; and to hide my TOR usage from the ISP.

Thank you

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2

Having a VPNBOX in front of your model has the same effect as having a VPN installed on the host operating system. No special documentation required.

This applies:
User → VPN → Tor → Internet

If any application, the full operating system is forced through the VPN first then this includes Whonix. No special exceptions.

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