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Code for DC CryptoParty Agenda | March 5, 2019

Circumventing censorship with Tails

Bring your phone, tablet, computer, or pen/paper to follow along!

Code for DC CryptoParty Ethos

Privacy is a fundamental human right. It is recognized in many countries to be as central to individual human dignity and social values as Freedom of Association and Freedom of Speech. Privacy is where we draw the line on how far a society can intrude into our personal lives. It is user-defined and varies between individuals. You are the steward of your identity. You are the only person who has the right to disclose your personal story.

Remember to join #cryptoparty on Code for DC's Slack. If you plan on eating pizza 🍕, remember to RSVP on meetup.

Today's Session


Tails is a distribution of linux built on DebianStable (Stretch 9.8). Tails is an acronym which stands for "the amnesic incognito live system." It's a specialized operating system designed for maximum privacy. Today we'll discuss each component of Tails's how how to use it for common online tasks.

Takeaway from today’s session:

  1. Navigate the internet anonymously with comfort and ease.
  2. An understanding of the distinction between a persistent live OS and a full install OS.
  3. Awareness of how to create your own Tails live USB stick.
  4. Stomach full of pizza.


  • The
  • Amnesic = Tails cannot store any record of your activities on the machine it's occupying. Think "zombie computer."
  • Incognito = Tails routes all system traffic through the TOR network. Who's been here before and can explain what TOR is?
  • Live System = Tails is a bootable "live" operating system meaning the system state state persists only in memory. Once the computer powers down, it dumps the contents of RAM and the record of your work disappears.


  • Tails "forgets" everything each time you power down the system.
  • Loads the OS completely "fresh," as if it were the first time booting a brand new machine.
  • Shutting down the computer actively wipes the machine's RAM to prevent data remanence after shutdown. Protects against cold boot attack. But what if I need to save some files?
  • Tails is fully amnesic by default, but it has a "persistence" option.
  • Sets aside space on USB, fully encrypted, which you can unlock with a password at boot or leave encrypted and boot a fully-amnesic state of Tails. Note: files stored outside the "Persistent" directory will still be erased on shutdown.


  • Leaves no trace on the host machine that it was ever used.
  • Uses Tor to enforce anonymity throughout the operating system.
  • Instead of just passing browser traffic through the Tor network, all applications on the system are routed through Tor network with a SOCKS5 proxy.

Live System

  • Operating system that runs off a DVD or USB.
  • Doesn't modify the contents of a computer's hard drive, it simply boots the operating system onto the computer's RAM.
  • System runs entirely on the RAM, could remove the hard drive from the machine.
  • Makes system very interchangeable between computers.

How to boot into Tails

From Apple hardware:

  • Restart your computer, hold the ⌥ alt / option key on the left side between the ⌘ command and ⌃ control keys.

Other computer:

  • Follow the instructions from your BIOS to open the boot menu(F12 is a commonly used key).


  • Select the USB drive that appears as an orange icon on the right side.
  • Click the ↑ arrow point upwards.
  • Press "return" to select Tails from the boot menu.
  • Click the blue start tails button once you've reviewed the settings and are comfortable with the level of security for your current situation.
  • Connect to WiFi.

Verify TOR network connectivity

  • Use the onion network analyzer

Other Linux Distros I think are pretty security conscious but also have offensive capabilities

Not linking directly to them, but here are some lists made by people who agree:

Want to lead a CryptoParty?

Is there a topic in digital security you're particularly interested in? Leading a CryptoParty is a great way to learn more about emerging cryptographic and security concepts. We are looking for folks with all kinds of backgrounds and interests to share their knowledge and interest. Talk to @csethna or @Ed O. on Slack if you're interested!

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