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Tails: The Beginner’s Guide

By Alex Nimoy Oct. 14, 2019, 8:38 a.m.

What is Tails OS?

Tails, acronym for The Amnesic Incognito Live System, is a Debian-based Linux Operating System built for the sole purposes of anonymity and privacy. First released in 2009, Tails has a long positive history of providing its users the privacy and anonymity they need when doing their online activities. In 2013, a former NSA contractor named Edward Snowden, as well as the group of journalists he communicated with for leaking NSA documents regarding mass surveillance schemes, have all
revealed that they used Tails to secure and anonymize their communications. What’s more, in 2014, a slide of an internal NSA presentation was published, in which it was clear that NSA considered Tails a major threat to its missions.

How Tails works?

Unlike Whonix—a sibling Linux distro with the same anonymity purposes—Tails is designed and meant to be live booted from removable media devices such as USB sticks and DVDs. In other words, instead of being installed on a computer’s hard drive, as is the case with most operating systems, Tails is typically installed on external mediums which can be plugged in/inserted and booted from on any computer.
Since Tails is stored and booted from an external medium, this means that the computer used will not change in any way, and thus no digital footprint, of Tails or the activities done with it, will be left on the computer. The computer’s hard drive is typically not modified nor even accessed; all that Tails use are the RAM, which is erased right when the computer shuts down, and the external medium itself.
The term amnesic in Tails’ name means that all files and modifications done or created during a working session will not persist to the next session. Put differently, Tails will roll back to its original state as a newly installed instance whenever it shuts down. However, this can be changed if users want to keep files and documents for future use.

Why use Tails?

As with Whonix, all incoming and outgoing traffic is forced to go through the Tor network, otherwise the traffic is blocked. Tails comes with a plethora of preinstalled software and applications, most of which are programs to aid users in their privacy and anonymity endeavor, and all are preconfigured with security and privacy in mind. Some of these useful programs are:
• Tor browser, as probably guessed. Tor’s native anonymous web browser.
• Electrum, a Bitcoin and cryptocurrency wallet for pseudonymous money transactions.
• PWgen, a strong random password generator.
• GnuPG, an OpenPGP implementation for encrypting and signing emails and data.
• MAT, a useful tool to anonymize files metadata.
• VeraCrypt for encrypting and hiding volumes.
• GNOME virtual keyboard, a countermeasure for potential keyloggers.

Using Tails

Note: this tutorial assumes you’re using a Debian-based Linux distro for verifying and installing the Tails image.
This tutorial will walk you through downloading ,verifying and installing Tails image. You’ll need:
• A USB stick with at least 8GB storage size.
• The latest Tails USB image which you can download from the website here

Verifying Tails image

After downloading the image, a signature file might be be included in the downloaded folder depending on whether you chose direct download or BitTorrent. If the signature is not included, however, you can download it separately from the same download page.
Put both the image and its signature file in a single folder. The contents of this folder should look like this:

Subsequently, you will need to download Tails’ signing key, which is also on the same page from earlier.
The key file has a .key suffix and needs to be imported to GPG (a PGP implementation) before verifying the signature.
Open the terminal and head to where the key’s been downloaded. To import the key into GPG, type:
Now Tails’ key has been imported. We can now verify the signature, and thus ascertain the authenticity of the image.
Head to the folder from earlier where both the image and the signature are, open the folder in a terminal and type:

gpg –verify tails-amd64-3.15.img.sig tails-amd64-3.15.img

The output should look something like this:

Good signature means the image is authentic.
Installing Tails on a USB stick
Now that we’ve verified the image, it’s time for installing it on a USB stick. GNOME DISK utility is installed by default on most Linux distributions. We’ll use this utility to install our Tails image on the USB stick as follows.
1. Start GNOME DISK (disks) utility.
2. Plug in the USB stick. It should appear at the left side of the disks utility.

  1. As shown in the screenshot above, my USB stick is visible in the left side of the window and is highlighted. Click on button pointed to by the blue arrow above, a small window will drop,choose restore disk image. You’ll be asked to specify the image, choose the one you downloaded earlier.
    After the disk utility had finished, everything will have successfully been installed on your USB stick, and you will want to boot from it now. While having the USB stick plugged in, power on you PC and quickly hit f9 (this depends on your PC manufacturer, on HP for example, it’s f9 ,and on Toshiba it’s f2.
    Google your PC manufacturer to find out what key works for you). After hitting the proper key, you will be taken to the boot menu, choose to boot from the USB stick you have Tails on.
    By now you should be seeing Tails’ Desktop screen. Have a look around and familiarize yourself with the pre-installed privacy and security focused programs, and most importantly, read the documentation.
    Especially the warning section in the documentation, which explains what you should expect from Tails and what you should not.

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