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Full Title or Meme

TAILS is a secure operating system (and a set of applications) designed to be booted off of a DVD or USB thumb drive.


It is too easy for a bad actor to tail you on the internet.


TAILS is easy to transport, but also ensures that TAILS can be booted and instantly useful from nearly any PC, Mac, or Chromebook. TAILS is built on Linux, a name you might recognize because it’s a popular, free, and open-source operating system that’s been available since 1991. TAILS, in particular, runs on a variant of Linux known as “Debian,” which became available in 1996. TAILS hit the big-time in 2013, when famed whistleblower and NSA contractor Edward Snowden used the software to contact reporter Glenn Greenwald at The Guardian newspaper in England and documentary filmmaker Laura Poitras. Snowden actually insisted that to communicate all three use TAILS along with all of its various built-in security and anonymity tools.

TAILS is powerful for three reasons. First, it’s as portable as a USB stick, which is far easier and more discreet to carry than a laptop. That portability, along with its software design, makes it easy to run off of nearly any host computer. Second, using TAILS on a host computer in the correct fashion leaves no traceable data behind as to any of its user’s online activities. It even comes pre-packaged with a suite of its own free software tools, allowing its users to work efficiently and without needing to disturb or use the host computer in any way. Third and most importantly, when setup correctly, TAILS helps ensure that all of your communications — email, web browsing, chat, and more — are encrypted, made anonymous, and then routed in such a way that it’s extremely difficult to detect or trace them.

To better explain how this power is provided, let’s start with its name: TAILS. TAILS is an acronym for “The Amnesic Incognito Live System.” As shown in the details below:

  • The
  • Amnesic, as in amnesia, because the TAILS system is designed, by default, to forget everything. It does this by not using the computer’s hard drive to store information. It uses the computer’s RAM (or memory sticks) instead. Because RAM is erased when a computer is shut down, TAILS leaves no trace once the computer hosting it is shut off. By default, each and every time you power TAILS back on, you are presented with the equivalent of a brand new, freshly imaged computer that’s never been used.
  • Incognito, as in “undercover,” because TAILS is designed to work anonymously and, therefore, protect your identity. It does this by forcing all outgoing connections through the TOR network, a technology I reviewed earlier on in “The Firewall.” TOR (an acronym for “The Onion Router”) is a system of relays which makes tracking anyone’s online web browsing extremely difficult. The TAILS operating system takes using TOR to an extreme: it forces all key communications over TOR, including web browsing, email, internet chat, and more.
  • Live, as in “living,” because, in the tech world, a live system is a system that is only installed onto a CD, DVD, or USB thumb drive. Nowhere else.
  • System, as in “operating system” (or OS), because TAILS is an entire operating system, just like its cousins Windows, Android, mac OS, and iOS. Unlike its cousins, however, TAILS is designed to be small, portable, and extremely secure.

How Do You Set It Up? While I’m a huge fan of having TAILS out there as a tool for those who need it, its setup process is convoluted and takes hours. I mean that literally: two hours. Just have a look at the Mac installation page or the Windows installation page if you think I’m kidding:

That’s right, friends — the setup on a Mac or PC requires 120 minutes, seven steps, three restarts, two USB sticks and — most likely — one massive headache. As a bonus, if you’re not fully frustrated or scared yet, the setup on a Mac also requires you to type out a UNIX command that looks something like this:

 sudo dd if=tails-amd64–3.8.iso of=/dev/disk3s1 bs=16m && sync

If you don’t know what that means — and most of you don’t — TAILS provides a primer on how to add that command; but still, don’t expect tech pundits like Leo Laporte, Walt Mossberg, David Pogue, Jean-Louis Gassée, and The Kim Komando Show to tell you how fun and easy TAILS is to set up. It just ain’t.

What Kinds of Tech Does it Provide? TAILS provides a host of great, free, open-source applications and tools to help ensure that (a) there’s an app available for everything you need to do and (b) all that you do online is secure and anonymous. If you’re wondering just how powerful these tools really are, many of them are known by the NSA to be difficult or impossible to break. This includes:

The TOR browser, for safe internet browsing KeePassX, a great application for generating and safekeeping of all of your various passwords Thunderbird, for emailing, secured by the Enigmail extension to encrypt and authenticate emails using a well-know and secure protocol called “OpenPGP” Pidgin Instant Messenger, for live chats, which are secured by the Off The Record (or OTR) encryption OnionShare, for safe sharing of files over the TOR network LibreOffice, for open-source versions of every standard office application you’ve come to know and love

When you boot into TAILS, it looks and works in ways that should be recognizable, whether you’re used to a Mac, Windows, or Linux operating system: you double click to open folders, you single click to open a menu bar, you have a home folder where you can keep files, and there are system options that you can alter to suit your preferences. Here’s a video I made to give you a simple and quick look at what the desktop looks like when you boot into TAILS. I should mention that I made this video by booting TAILS into a virtual machine (or VM) and then recording my screen. Please note: never use TAILS in a single VM if you need to ensure your anonymity and security.