Creating My “Secret” Identity with Whonix

by secrets of the dark

It’s been said over and over by those who know what they’re talking about: “Don’t use Windows on the deep web!”  In fact, one of my favorite YouTubers, SomeOrdinaryGamers, specifically has a video that goes by this title: DON’T use Windows On the Deep Web!

I even wrote a song parody about it(sung to the tune of “Jesus Loves the Little Children”):

Don’t use Windows on the deep web,
You’ll get viruses and spam!
They will hack all of your files,
While they’re hunting you for miles,
Don’t use Windows on the deep web or you’ll die!


A recent Lifehacker article entitled “How Can I Stay Anonymous With Tor?” essentially said the same thing: “Don’t use Windows.  Just don’t.  This also means don’t use the Tor Browser Bundle on Windows.  Vulnerabilities in the software in TBB figure prominently in both the NSA slides and FBI’s recent takedown of Freedom Hosting.”

On top of that, as you may know, because Windows is the most popular operating system out there, a lot more malware is designed to infect Windows systems.

Live Nude Operating Systems!


So, if you are a Windows user who wants to explore the Tor network, what’s the alternative (besides buying an entirely new system)?

This is where live operating systems come in.  There are in fact numerous live OS’s (almost too many to count).  Of course, they vary greatly in what features they offer, how they’re set up, how secure they are, and most importantly…how difficult they are to learn!

Just to name a few that exist: Arch Linux, Tails, SystemRescueCD, Xubuntu, Lubuntu, OpenIndiana, Puppy Linux, HandyLinux, and VectorLinux.  To find more, see the full list of live OS’s at The LiveCD List.

Whonix (Insert Owl Joke Here)

The live OS that I’m currently teaching myself (or rather, attempting to teach myself) is Whonix.  I only say “attempting” because my experience thus far has been a lot of trial-and-error.

Whonix is a Debian GNU/Linux based operating system that’s concentrated on privacy, anonymity, and security. This is their official site, if you’re interested: Whonix – Anonymous Operating System.

It consists of two parts: Whonix-Gateway, which runs the Tor network, and Whonix-Workstation, which is on a completely isolated network (and runs end-user applications, like in the picture below).  Like other live OS’s, Whonix is designed to preserve security while, at the same time, still being relatively easy to use.  It includes its own web browser, IRC client, word processor, and other features.

The actual layout looks roughly like this:


What Are Its Advantages?

One major difference between Whonix and other live OS’s like Tails is that Whonix does not boot via a Live CD or DVD.

According to is developers, the reasons for this are that since the system doesn’t boot from a Live CD, it can be (for the most part) actively maintained.  It is also a hardened GNU/Linux distro.

Beyond that, though its interface may take some getting used to, it is relatively easy to pick up, once you know your way around.

Be that as it may, Whonix (like any “anonymity” system) is not perfect, and can be broken by user errors.  For example, it’s extremely foolish to log into your real-life Facebook account while using Whonix (or the Tor network in general).  The same goes for your bank account, Paypal, eBay, Etsy, etc.  For a full list of what not to do while using Whonix, see DoNot – Whonix.

Anonymity software may hide your IP address, and/or location, but if you log into a network like Facebook or Google+ (to which you’ve already given your personal details), that basically negates the anonymity aspect.  In addition, because the Tor network disguises your IP address, it will likely appear as if someone from a country besides yours is attempting to access your account (which will raise suspicion).

So far, though, I’ve found it quite easy to use, and though it has some quirks, it seems pretty trustworthy as far as privacy goes.

Personally, I love that its “sandbox” environment (again, like most live operating systems) can more or less make all of your activities private.  Technically, Whonix cannot even find out its own IP address, making it akin to a spy with amnesia.  Any new operating system will take adjusting to, but so far, it feels pretty intuitive.

Hopefully, I won’t say that and then get this message:


Nah, I’m a space ninja.


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Have you heard of the dark web? Simply put, it's the "hidden internet" built on networks like Tor. "Secrets of the Dark" chronicles my dark web experiences, but is also aimed at demythologizing it and teaching about it. Want to reproduce one of the "horror stories"? Contact me at

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