Online Privacy using

GPG, TOR, and Tails

Created by Amber Adams / @amberadams aka @anarchival

view this presentation on the Web

Right to Privacy


  • Lynn Root's presentation on NSA surveillance
  • PRISM Break
  • Why Metadata Matters
  • Greg Greenwald debates Michael Hayden
  • The Law

  • SCOTUS ruling on warrants and cell phones.
  • White House issues a report on Big Data.
  • Net Neutrality and the FCC.
  • Law Enforcement

  • U.S. counter-terrorism officers investigated Occupy.
  • Subject to surveillance: Civil Rights and Suffragettes.
  • Draconian prosecutions of hackers such as Aaron Swartz, Andrew Auernheimer, Matthew Keys, Deric Lostutter, and others...
  • Coders are the new Communists?

    Heart Bleed

    The Heartbleed bug is a programming

    error in the OpenSSL library which

    undergirds most of the

    encrypted traffic on the Internet.

    (speaking of encrypted traffic,

    even once the bug is fixed,

    you should be using

    HTTPS Everywhere

    from the EFF).

    Targeting Pregnancy

    They know you're pregnant,

    Maybe even before your family does.

    (you should install Privacy Badger from the EFF).


    Creeps can use your own computer

    to stalk you often with terrible consequences.

    hack or be hacked


    The Onion Router

    Traffic Analysis

    Sherlock Holmes reveals your IP, specs on your system

    easy to find your location based on your IP

    before even analysing the content of your unencrypted messages

    Proxies & Encryption


    Hide My Ass

    Installation & Use

    Download and install the package.

    Start the TOR browser, click Connect.

    Use *only* the TOR browser

    Use HTTPS (enabled by default)

    Use bridges and/or find company

    Don't torrent

    Don't enable or install browser plugins

    Don't open documents through TOR while online

    Hidden Services

    Explore the Deep, Dark, Mysterious Net.

    Host your own hidden services on a virtual machine.

    Host your own torrents while you're at it, too.


    The Terminal

    Mac: Finder -> Applications -> Utilities -> Terminal

    Linux: Browse to your Terminal application

    (you probably already know where it is)

    Windows: Install and use Cygwin

    or partition your hard drive and dual boot to Linux

    Linux Installfest @ PhreakNIC, Halloween weekend at the Maxwell House Hotel in Nashville.

    Learning to Love the CLI

    A short introduction on the Web.

    The man(ual) pages.

    In the Beginning Was the Command Line by Neal Stephenson.


    Installation & Use

    Mac: GPG Tools

    Windows: GPG4Win


    							gpg --version
    							sudo apt-get install gnupg

    Create Your Keys

    							gpg --gen-key
  • Choose option #1: RSA and RSA
  • 2048 is the default encryption strength, but you can go lower or higher
  • You can choose your key to Never expire, or set an expiration
  • Type 'y' to confirm choices
  • assign the user, an email address, and an optional comment
  • dozens of tiny hamsters, spinning in their cages, generating crypto!
  • Add Accounts to Your Key

    							--edit-key 12345678

    Exporting Your Public Key

    							gpg --armor --output mykeyname.asc --export
  • attach the file mykeyname.asc to emails you send
  • other GPG users can import this key into their trusted database
  • once you have exchanged keys, you can exchange encrypted mail
  • mail clients can handle this attachment automagically; most webmail requires manual attachment
  • Import a Trusted Key

    							gpg --import pubkeyfile.asc

    importing from keyservers

    							gpg --keyserver --keyserver-options honor-http-proxy --search-keys

    Move Your Keys

    							user@desktop$ cp -r ~/.gnupg /media/jumpdrive/ 
    							user@laptop$ cp -r /media/jumpdrive/.gnupg ~/

    Encrypting Local Files

    							gpg --encrypt commies.list > commies.list.gpg
    							gpg --decrypt pink.list > pink.list  
  • you will encrypt the file for a person(s) in your keychain
  • to encrypt an entire directory, pack it into a .tar first
  • remember to delete the original, unencrypted file!
  • Mail Clients

    Enigmail plugin for Thunderbird

    Evolution Mail: Edit -> Preferences -> Accounts -> Security Tab -> Key ID

  • remember to delete the original, unencrypted file!
  • Revoking a Key

    							gpg --output revoke.asc --gen-revoke 12345678 


    Off The Record Messaging


    No one else can read your instant messages.


    You are assured the correspondent is who you think it is.


    The messages you send do not have digital signatures that are checkable by a third party.

    Perfect forward secrecy

    If you lose control of your private keys, no previous conversation is compromised.

    Installation & Use

    Install Pidgin.

    Install OTR.

    sudo apt-get install pidgin
    sudo apt-get install pidgin-otr

    Enable OTR plugin & generate key.

    Manage permissions.



    All software is configured to connect to the Internet through Tor. If an application tries to connect to the Internet directly, the connection is automatically blocked.

    Use Anywhere, Leave No Trace

    "Amnesic" because the only storage space it uses is the RAM on your computer, which is automatically erased when the computer shuts down.

    Cryptographic Tools

    LUKS, Linux standard for disk encryption

    HTTPS Everywhere

    encrypt and sign emails, documents with OpenPGP

    protect IMs with OTR

    securely delete files with Nautilus Wipe

    Installation & Use

    Download the Tails ISO using bittorrent

    Download and verify the Tails signing key.

    Burn the ISO image to a disc.

    Boot your computer from the disc.