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Tall Tails

Nate Drake explores how to configure the latest version of Tails for maximum security and convenience.

Total online anonymity is impossible, but if used correctly, the or network, or dark net, comes pretty close. This is the thinking T behind Tails (The Amnesic Incognito Live System), a Debian-based security-focused Linux distro. Since 2009, the good people of the Tails Project have hitched their star to Tor’s wagon by making sure that whenever you use the OS, all internet connections are routed through the dark net.

If you’re new to the dark net and want to familiarise yourself with how Tor is configured to conceal your identity, it’s now time to stop. Head on over to www. torproject.org and return here when you’re done.

If, on the other hand, you’re happy the dark net can provide the online safety you need, you can do far worse than use Tails. Instead of offering a standalone browser, you have an entire OS geared towards keeping you safe online. Connections outside Tor are blocked (with one exception, as you’ll learn) and the system can be run in amnesiac mode. In other words, it can load into your device’s RAM, then erase critical data on shutdown. This makes it almost impossible to recover your data using current digital forensics.

Tails also supports a persistent mode, whereby you can create an encrypted partition on a USB stick to store vital settings, like browser bookmarks and Wi-Fi passwords. In this guide, you’ll learn how to set up and configure this, as well as the pros and cons of doing so.

What about the Tor Browser?

First, let’s address the elephant in the room. The Tor Project does indeed offer the Tor Browser, which by default doesn’t store your browsing data and also routes all connections through the dark net.

Tails itself uses an implementation of the browser (currently v12.5.6) with the uBlock extension, so the Tor Project must be doing something right.

Still, Tails offers a number of advantages over just installing the Tor Browser on your regular machine. Firstly, even browsers run in private mode like the Tor Browser can leave traces; such programs save files temporarily to your machine’s hard drive, so they can be recovered to build up data on your browsing habits.

The Tor Browser also doesn’t use any encryption, so anyone with access to your user account can open it to view your bookmarks and/or view your connection settings. The same applies to any files you download.

When it comes to sharing files, if you’ve prepared them on your personal device, there’s always a risk they could contain identifying metadata, even if sent via the dark net. Tails makes it easy to remove this information, plus files created in live mode naturally don’t contain any metadata from your hard disk.

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Linux Format
January 2024
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