August 2014 CIALUG Meeting: TAILS: The Amnesic Incognito Live System

Here’s a quick write-up from my presentation on The Amnesic Incognito Live System (TAILS) at the August 2014 CIALUG meeting.

The main TAILS Web site: https://tails.boum.org/

TAILS is intended to make it easy for non-technical end users to boot into a live, Linux-based OS which automatically routes its traffic over The Onion Router (TOR) network. The intention is to provide anonymity, privacy, and plausible deniability for dissidents, whistle-blowers, or anyone who feels the need to conduct searches or communicate securely while leaving little to no trace of those activities on the host system.

While TAILS does succeed at providing a bootable system that defaults to a TOR-routed connection, non-technical or even non-Linux end users will need some training from a more savvy user to make the best use of this system. Keep the following points in mind:

  • TAILS is still susceptible to any issues which effect the TOR network. Know and understand how to limit your behaviors when using TOR and apply those to your use of TAILS.
  • Out of the box, the current version (as of this writing, 1.1 released July 2014) of TAILS had 34 packages which were out of date, and TOR itself was one of those pending updates. Installing updates before each use should be top priority, but more on that later.
  • It does NOT appear that TAILS uses the TOR Browser Bundle. This makes it more important to apply updates before each use as Firefox, Vidalia and the TOR Button may need to be updated (no updates were pending for these in version 1.1 as of this writing).

As mentioned above, the very first thing which should be done after successfully booting to TAILS and connecting to the Internet and TOR network is to apply updates. This is accomplished by logging in to a terminal, elevating to root, and running ‘apt-get update’ followed by ‘apt-get upgrade’. Note that I ran in to the following issues when updating version 1.1 of TAILS in this manner:

  • Updating was slow. This is actually a good thing because the updates are grabbed via the TOR network.
  • When the TOR package gets updated, it prompts whether or not to replace the configuration. I recommend keeping the existing configuration (the default choice).
  • When the TOR package gets updated, it stops the TOR service but doesn’t restart it. Later in the update process, some other packages need to download firmware. Because the TOR service is stopped, that process fails. I had to start the TOR service again, then re-run ‘apt-get upgrade’ to successfully update those packages.
  • When the TOR package gets updated, it breaks the running Vidalia process. I simply closed it. TOR continued to work without that process running.

While this isn’t a complete summary of my presentation, I hope it is helpful. Please share this post if you found it so. Thanks!