A look at TAILS – Privacy oriented GNU/Linux Distribution

Mike Turcotte-McCusker
Sep 12, 2017

It’s no secret that using GNU/Linux is generally safer than using Microsoft Windows, however, there are specific distributions of GNU/Linux that are even more focused on privacy and safety than the usual distros like Ubuntu. In a previous article, I showed of Qubes OS; and now it’s time to look at TAILS.

What is TAILS?

The Amensic Incognito Live System, is a Debian based distribution that routes all internet traffic through the TOR network, and leaves no trace of its existence or anything done on the system when the machine is shut down. The obvious aim in this, is to aid in keeping the user anonymous and private. Tails is not installed to a users computer, but instead is run strictly as a LiveUSB / LiveDVD.

TAILS does not utilize the host machines Hard Disk at all, and is loaded entirely into RAM. When a machine is shut down, the data that is stored in RAM disappears over the course of a few minutes, essentially leaving no trace of whatever had been done. Granted, there is a method of attack known as a Cold Boot Attack, where data is extracted from RAM before it has had a chance to disappear, but TAILS has you covered on that front too; the TAILS website says,

“To prevent this attack, the data in RAM is overwritten by random data when shutting down Tails. This erases all traces from your session on that computer.”

There are numerous other security minded applications found in a Tails install, which the website lists as:

  • Pidgin preconfigured with OTR for Off-the-Record Messaging
  • OnionShare for anonymous filesharing
  • Thunderbird email client with Enigmail for OpenPGP support
  • Liferea feed aggregator
  • Gobby for collaborative text writing
  • Aircrack-ng for wireless network auditing
  • Electrum, an easy-to-use bitcoin client
  • LUKS and GNOME Disks to install and use encrypted storage devices, for example USB sticks
  • GnuPG, the GNU implementation of OpenPGP for email and data encyption and signing
  • Monkeysign, a tool for OpenPGP key signing and exchange
  • PWGen, a strong password generator
  • Shamir's Secret Sharing using gfshare and ssss
  • Florence virtual keyboard as a countermeasure against hardware keyloggers
  • MAT to anonymize metadata in files
  • KeePassX password manager
  • GtkHash to calculate checksums
  • Keyringer, a command line tool to encrypt secrets shared through Git
  • Paperkey a command line tool to back up OpenPGP secret keys on paper

More applications can easily be installed as well, since Tails is based on Debian Stable, and has full access to the repositories. However, keep in mind that anything installed will disappear once the machine is shut down.

Installing Tails is not quite as simple as installing other distributions, and the method is a little different depending on if you’re using Windows, Ubuntu/Debian/Mint or other forms of GNU/Linux. For full instructions on how to install Tails, check out the guide found here.

So...Why would I want to use Tails anyway?

Tails is ideal for keeping yourself and your activities hidden as previously stated, which is absolutely perfect for those who want to do their best to have ‘big brother’ unable to spy on their activities, as much as possible. Another major use of Tails is to avoid censorship in places where internet use is carefully monitored; because Tails routes ALL internet traffic through TOR, you can be assured that you are able to freely surf the internet.

Tails is also used by some journalists, agencies, and whistleblowers. Edward Snowden for example, was using Tails to communicate with Glen Greenwald and others, when he released his famous leaks of classified information. The point being, that for those who are extremely privacy conscious, Tails is definitely worth looking at, even if you feel you have ‘nothing to hide’, having the peace of mind of knowing that if you DO ever need something like this; it’s easily accessible.

A look at TAILS – Privacy oriented GNU/Linux Distribution
Article Name
A look at TAILS – Privacy oriented GNU/Linux Distribution
The Amensic Incognito Live System, is a Debian based distribution that routes all internet traffic through the TOR network, and leaves no trace of its existence or anything done on the system when the machine is shut down.
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  1. CHEF-KOCH said on September 12, 2017 at 8:08 pm

    I’m not sure if Quobes OS, Tails, Whonix,… is the answer. For me it’s snake oil. Of course there proving several security layers, but the question is if it makes sense when they using the same software like on every other OS – and then you anyway are attachable by e.g. exploits, bugs and so. The thing with running everything in a virtual machine or in a virtualized kernel is that this allows attackers to hide or obfuscate their malware on a higher level without that you ever notice – in my opinion that isn’t one security feature it’s dangerous in fact most good malware checking already if there is something virtualized running or not, I’m sure such checks also exist for the OS/kernel. Personally I don’t think the OS by itself is more secure than a normal Linux/Arch distro when you mis-configure or use external software anyway. For just browsing it’s maybe fine but for the rest? I’m sceptical.

  2. rollins said on September 12, 2017 at 3:41 pm

    “Tails is ideal for keeping yourself and your activities hidden as previously stated, which is absolutely perfect for those who want to do their best to have ‘big brother’ unable to spy on their activities…”


    …of course a drawback to using Tails/Tor is that it highlights your internet presence to ‘big brother’ among all the other ‘normal’ browsers.

    If you wore a face mask walking around a crowded shopping mall… no one would know who you are, but you would attract much attention as a very unusual & suspicious person.

    Tails/Tor tells ‘big brother’ to pay extra special attention to this internet participant. Any mis-configuration or system error in your Tails/Tor could unmask you to those who probe your connection.

    1. Clairvaux said on September 12, 2017 at 6:12 pm

      Except there is no Big Brother. There is widespread tracking for commercial purposes, and those doing it won’t bother to unmask Tor users, it’s just not worth it.

      Big Brother-type concerns means your adversary is law enforcement, or even secret services. If you face that type of problems (whatever the reason), of course your interest is to build up Tor-like defenses, not to cavort around naked in the hope nobody will ever notice.

      This would the the equivalent of a soldier going to a war zone without a gun and armor, because guns and armor attract enemy fire. Well, of course they do.

      Besides, what are we talking about ? If you’re a real criminal (you sell drugs by the truckload, you organise media piracy on an industrial scale, you’re a murderer or a terrorist), or you’re a bona fide spy, then of course the police and assorted security services are already after you, and are likely to target you specifically. But then, Tor has been designed by the American Navy, precisely to assist spies, policemen and the like. There are perfectly legitimate uses for covert techniques.

      If, on the other hand, you tread in the grey zone of free speech (your government might object to you saying perfectly legitimate things, which just happen to be illegal, or simply frowned upon in your country), then you might not be such a high-value target after all, because even Big Brother has limited resources and needs to focus them on the biggest threats.

  3. Ben said on September 12, 2017 at 11:26 am

    You should make an article about whonix. I think it’s the best solution for most people, as with Tails you either need a different computer or reboot everytime (or run it in a VM which is a stupid idea).


    Whonix will use two VMs, one for a normal linux and one that only runs a Tor proxy. The linux VM is forced to go to the internet via the proxy VM. So if there are no VM escape exploits (well there are certainly some) this is quite safe.

  4. Clairvaux said on September 12, 2017 at 10:05 am

    Surprisingly, Tails is the only piece of software I know whose developer states that it is difficult to install and that you’ll be lucky if your install does not fail. The Tails Reddit mostly includes assistance requests from users who had some catastrophic failure with Tails, not from people asking for ways to do more with it.

    I have installed it successfully, but I haven’t managed to zoom in the interface to an acceptable size for easy reading.

    1. ams said on September 12, 2017 at 5:25 pm

      What is “it”? If you mean TorBrowser, it’s based on firefox and, same as when using firefox, you can press Ctrl+plus to “zoom in (enlarge)” and Ctrl+minus to “zoom out”.

      1. Clairvaux said on September 13, 2017 at 9:01 am

        Thank you, ams. I will dust off my Tails flash drive and try that.

      2. ams said on September 13, 2017 at 6:05 am

        my kneejerk reply would be: “in most desktop linux distros, you’ll find a pre-installed utility, `xrandr`, which enables you to change display settings, including dpi/scaling”

        To check whether Tails handles things differently, I did a quick websearch “query: change display resolution tails linux” and the immediate match was


        If that exact page doesn’t suit, one of the similar Q/A pages at tor.stackexchange.com probably will.


      3. Clairvaux said on September 12, 2017 at 5:43 pm

        “It” is the Tails operating system, and all the applications it comes bundled with. I’m not speaking about a Web page displayed by Tor, which, indeed, can be zoomed in an out in the classical way.

        I’m trying to find the equivalent of changing the dpi setting in Windows — which itself has a whole lot of problems, but it does work (give and take the occasional glitch) to scale upwards all the elements of the user interface of all the application software (and operating system, obviously). I use the 150 % setting.

        The native size is much too small to be read easily (at least by me).

  5. Robert said on September 12, 2017 at 6:39 am

    This is the way to go if you want to leak something and yet remain untraceable. I install this on a USB drive so it is separate from the main computer and it’s finger print. War driving for open WiFi in places where there is no camera for added security will lead a trail to a dead end should the feds be hunting. Privacy is not dead if you educate yourself and don’t do anything stupid like logging in with your Google account while using Tails. In a world where privacy is eroding on Windows, Mac and even Linux, there is still Tails. And Tails is updated constantly to patch known security flaws.

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