Tails (operating system)

3 min readSep 11, 2019

Tails or The Amnesic Incognito Live System is a security-focused Debian-based Linux distribution aimed at preserving privacy and anonymity. All its incoming and outgoing connections are forced to go through Tor, and any and all non-anonymous connections are blocked. The system is designed to be booted as a live DVD or live USB and will leave no digital footprint on the machine unless explicitly told to do so. The Tor Project has provided financial support for its development.

History

Tails was first released on 23 June 2009. It is the next iteration of development on Incognito, a Gentoo-based Linux distribution. The Tor Project has provided financial support for its development. Tails have also received funding from the Debian Project, Mozilla, and the Freedom of the Press Foundation.

Laura Poitras, Glenn Greenwald, and Barton Gellman have each said that Tails was an important tool they used in their work with National Security Agency whistleblower Edward Snowden.

As of release 3.0, Tails requires a 64-bit processor to run.

Bundled software

Networking

Tor with: Stream isolation, regular, obfs2, obfs3, obfs4, and ScrambleSuit bridges support.
NetworkManager for easy network configuration
Tor Browser, a web browser based on Mozilla Firefox and modified to protect anonymity with:
Torbutton for anonymity and protection against JavaScript with all cookies treated as session cookies by default;
HTTPS Everywhere transparently enables SSL-encrypted connections to a great number of major websites
NoScript to have even more control over JavaScript
uBlock Origin to remove advertisements.
Pidgin preconfigured with OTR for end-to-end encrypted instant messaging
Thunderbird email client with Enigmail for OpenPGP support
Liferea feed aggregator
Aircrack-ng for Wi-Fi networks auditing
Electrum, an easy-to-use bitcoin client

Encryption and privacy software

LUKS and GNOME Disks to install and use encrypted storage devices, e.g. for USB sticks
GnuPG, the GNU implementation of OpenPGP for e-mail and data encryption and signing
Monkeysign, a tool for OpenPGP key signing and exchange
PWGen, a strong random password generator
Shamir’s Secret Sharing using gfshare and ssss
GNOME 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
DeepOnion wallet, an anonymous cryptocurrency using Tor network

One may choose among a large number of languages and keyboard layouts when the system is booted.

In mainstream media

On 3 July 2014, German public television channel Das Erste reported that the NSA’s XKeyscore surveillance system contains definitions that match persons who search for Tails using a search engine or visit the Tails website. A comment in XKeyscore’s source code calls Tails “a comsec mechanism advocated by extremists on extremist forums”.

On 28 December 2014, Der Spiegel published slides from an internal NSA presentation dating to June 2012 in which the NSA deemed Tails on its own as a “major threat” to its mission, and when used in conjunction with other privacy tools such as OTR, Cspace, RedPhone, and TrueCrypt was ranked as “catastrophic,” leading to a “near-total loss/lack of insight to target communications, presence…”