Welcome to my Alice tea party! 🫖🎀
I decided to write a series of short posts about secure operating systems 🖥🐧

Today, we'll take a look at Whonix and find out if it's as good and anonymous as people say. Spoiler alert: no, it's not.

Let me clarify right away: Whonix is not a full-fledged operating system, but a tool for anonymity that can work independently or as a router in Qubes OS. In this article, I will focus on analyzing how it works as a standalone system

How does Whonix work?🧩
Whonix is built on two virtual machines: Whonix-Gateway and Whonix-Workstation. Gateway configures and routes all your traffic through the Tor network. Workstation is your workplace. If you want to dig deeper, check out their documentation.

Problems with Whonix 🔓
Now to the point: why Whonix isn't really necessary. Let's start with Gateway. It's just Debian with Tor pre-installed and a bunch of scripts that redirect traffic through Tor. Everything is tied to the configuration in the settings file and iptables rules. Cool? Not really. Plus, Whonix drags along old Debian, where packages are updated once in a blue moon.

Whonix positions itself as super protection against leaks, but if you don't understand what you're doing, no virtual machine will save you. For example, if you run a browser with JavaScript or download files and then open them outside of Workstation, your anonymity is gone.

By the way, Whonix can only be run without problems on VirtualBox. You may argue that there are versions for KVM/QEMU on their website. But that's where the problems begin. If you take Whonix for KVM, you won't be able to install it just like that — you need to edit the configuration, and there are no detailed instructions on how to do this anywhere. With VirtualBox, however, there are no such problems — everything works out of the box.

But what's wrong with VirtualBox?🪤
Besides the fact that it is significantly slower than KVM. In March 2025, a vulnerability CVE-2025-30712 with a rating of 8.1 appeared in Virtualbox. It allows an attacker with access to the host system to perform a VM escape, i.e., to get out of the virtual machine onto your main computer🫠. Proof-of-concept is already circulating on the network, and exploitation is easier than it seems. If the host is compromised, all your anonymity goes down the drain, and your real IP or other data may leak.

How to make an analogue of Whunix Gateway? ⚙️
But there is another way. The Gateway model itself is not bad. But you can create a machine with it yourself without Whunix, using a minimalist Linux (such as Gentoo or even FreeBSD instead of Linux). Then configure Tor directly. After all, Gateway is just a wrapper around the standard Tor and iptables settings, which can be found on Google in five minutes. Now add the iptables you found and DNSPort to the Tor config so that DNS requests also go through Tor, and that's it. This takes up less space and reduces the attack surface.

Conclusion
To be fair, Whonix isn't always bad. But it can be useful in conjunction with Qubes OS (where it runs in KVM, by the way), which has additional security mechanisms, such as domain isolation, that enhance security. But apart from Qubes, Whonix is pretty pointless. You might think it's suitable for those who don't want to bother with configuring Tor, but that's not the case. To run Whonix on a decent VM, such as KVM, you'll have to go through just as much trouble.

The bottom line is simple: Whonix is not a super-anonymous OS, but a tool that complicates life more than it protects it 💊

I hope you found this useful.❤️✨ If you wish, you can explore the topic yourself by reading research and testing the system.

Here are some good articles about Whonix:
THESIS.pdf — here is an overview of anonymous operating systems, including Whonix.
Whonix and Tor Limitations — about the shortcomings of Whonix and Tor.
JOSH Article — analysis of Whonix limitations.

#anonymity #linux #whunix #cve #anonymity_os #tor #security