Making it work

Tails works by booting your computer off of an external disk — usually a USB drive, an SD card or a CD — but getting Tails onto the right storage drive is harder than it sounds. Ideally, you’d keep it on a CD: once it’s burned into the plastic, the code can't be changed, making it completely immune to malware. But with new versions being released every few months (and plenty of laptops going without CD drives), a USB stick can be more convenient. We used Rufus to make a bootable version on a USB drive and SD card, but even then, certain flash drives simply won’t work with Tails. There are ways to add encrypted storage or persistent programs too, but each extra feature is also a new chance for security problems.

there are lots of ways to accidentally break your own security

Getting Tails onto a computer isn’t straightforward either. There’s a long list of computers that can’t run the OS, and it includes most of the computers made by Apple. We spent the better part of a day trying to launch it on a Toshiba Kirabook, only to have Windows 8 punch through every time. It ends up working best on machines that are Linux-friendly, without anything like a high-powered video card to trip things up. There are a few different stable setups, but lots of ways to accidentally break your own security.

In exchange for all the troubleshooting, you get an unusual kind of anonymity. Keeping the operating system on a disk means you’re operating independent of the computer, picking nothing up and leaving nothing behind. It also makes your setup portable. You can launch Tails from an internet cafe and know that none of the programs on the public computer will get in the way of what you’re doing. The new versions of Tails will even hide you within a local network, randomizing the computer’s MAC address to make you even harder to track. None of the methods are completely impenetrable, but together they add up to a major headache for anyone trying to follow you across the web.

Even if the developers wanted to put in a backdoor, they couldn't

Getting there has been a five-year process, with developers working in their spare time on a miniscule budget — less than $60,000 a year in donations, before the recent grant. The code has been open for review at every stage, and after each release, auditors have found holes in Tails' security, creative ways an attacker might circumvent the program. The holes are patched a few months later, then new holes are discovered, then those holes are patched a few months after that. By now, this process has repeated more than 30 times. It's the nature of open-source development, a messy, public process that produces secure software through a slow grind of bug hunts. That parade of public security failings is meant to make users feel safe. If there's a problem in security at any level, you'll know about it, and the team will be under pressure to fix it as soon as possible. It's the same open workflow that built Tor and PGP, and stumbled more recently with the Heartbleed bug. But it means that even if the developers wanted to put in a backdoor, they couldn't.

Even more remarkable, no one knows who's behind it all. The development team works under pseudonyms and their legal names have never been publicly revealed. "Some of us want to remain anonymous," the Tails developers told me from a group email account. "Some of us simply believe that our work, what we do, and how we do it, should be enough."