Increasing your privacy and anonymity through Tails

According to Tails, it is a live system (Linux live system that can run on USB or CD) that aims to preserve your privacy and anonymity by masking your online presence with Tor and I2P.

Whats good about it is that since it comes with a live system, it therefore allows you to bring your media (USB, SD) so that wherever you go, your bring anonymity with you.  Plus it has its own of software suite that you can use like a browser, a messaging client, email client, office suite, and the like.

Another benefit of Tails is that it uses the Tor framework. Tor is basically an open distributed network (no single point of server – in fact every Tor node is a Tor server) that masks (encrypts) and bounces the traffic between those nodes.  The benefit of this is that your location is not seen as well as there are no man in the middle attacks between these bouncing of traffic between Tor nodes.  You however, should still use GPG or SSL as encryption for end to end communication because Tor does not encrypt the traffic after passing the Tor end node.  Another benefit of Tor is that you can consume services or see websites available only in Tor as .onion domain.

The I2P technology that Tails uses is an anonymity overlay network.  It is an additional layer (simple encrypted layer) above the TCP/IP (unencrypted) which make sures that your end-to-end connection tunnels are secured.  Basically it protects you from your ISP and your local proxies from spying on you.

That having said, you as a user still have to make sure to use all the tools incorporated with Tails so you can be totally secured.  Some guidelines include:

  1. Encrypt your USB sticks
  2. Use HTTPS instead of HTTP
  3. Encrypt and sign your emails and documents using OpenGPG
  4. Use the OTR to encrypt instant messaging channels
  5. Secure delete your files and clean your disk using wipe.

With all said and read, here’s how I installed Tails.

  1. Download and verify its ISO image file
    1. Windows:
    2. Mac:
    3. It is preferred to use Torrent since it automatically validates the ISO.
  2. Install the intermediary Tails on your first USB
    1. Windows:
    2. Mac:
    3. Follow instructions above to install on Windows or Mac.  This intermediary Tails is needed in order to install Tails using its own live system, which ensures that all are secure.
    4. What I did with my system is that I burned the ISO image into a DVD since I don’t have a USB boot on my old MacBook laptop.
  3. Install the final Tails on your second USB
    1. Windows:
    2. Mac:
    3. Install this final Tails on a higher size USB as this will contain your Tails live system, as well as your encrypted documents, emails, configuration, etc.
    4. Once done, you can delete the intermediary Tails. Intermediary Tails is just a pawn to install Tails into a more usable final version.  What good does it have, if Tails cannot store your documents in it securely.
    5. This final USB then can be booted from any computer that boots from USB.
  4. Create an Encrypted Persistent Storage
    1. Start the final Tails
    2. Go to Applications > Tails > Create Persistent Storage
    3. Select Personal, then click Create
    4. Restart


Accessing Tails using Administrator

Tails is still in the buggy stage since it is still being developed heavily.  It just started to be conceptualized since 2013 and some of its underlying framework i.e. the I2P are not yet mature.

CAUTION: When you enter Admin mode, it may update itself and if you cannot connect to the Tor network, it may hang leaving you no option but to restart.

Also, when you restart or shutdown, you may encounter a hang after the screen goes black that says attempting to wipe the system memory; and that if the system does not power off automatically in a few seconds, it may mean that the memory wiping has failed.  But the system hangs and doesn’t proceed after this.  This is a known issue in Apple MacBook systems.

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