Down the Security Rabbit Hole
The most secure and anonymous communication tools available
David Koff August 27 2018
These tools are used not only to lock down your security and anonymity on the known internet, but also to access the portions of the internet that are normally hidden — “The Dark Web.”
most of us don’t need the same high-privacy, high-security tools that confidential informants, journalists, and whistleblowers use, we should all know about these tools in case the time comes when we actually need them.
It’s also worth reminding everyone there’s no such thing as perfect digital security on the internet.
TAILS is an acronym for “The Amnesic Incognito Live System.”
TAILS is a highly-secure operating system (and a host of cool applications) designed to be booted off of a DVD or USB thumb drive. This not only makes TAILS 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.
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.
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
TAILS even published a page of possible ways that its own security can be compromised.
Whonix (pronounced “HOOnix”) is an OS focused on anonymity, privacy, and security. Like TAILS, it is built on the open source Debian Linux OS and on TOR, the decentralized network which randomizes and segments your data transmissions.
Its unique approach to offering such well-regarded security is the creative use of two virtual machines (or VMs) running in tandem on one host computer. One of these VMs is known as the Gateway while the other is known as the Workstation.
Compared to TAILS, Whonix only provides a few free, open-source applications and those need to be set up fairly extensively. The list includes:
- The TOR browser, for safe web browsing
- Firefox, for less secure web browsing
- Icedove, for emailing, secured by the Enigmail extension to encrypt and authenticate emails using a well-know and secure protocol called “OpenPGP”
- HexChat, for internet chats
- VLC, to open and view every kind of video file that’s ever existed