Performance Objective

At the conclusion of the course the student will be able to:

  1. Identify what TAILS OS is.

  2. Identify one reason you may wish to use TAILS OS.

  3. Explain how TAILS OS works.

  4. Describe one method to install TAILS OS.

  5. Describe a security event in relation to TAILS OS.

Introduction

The Amnesic Incognito Live System. is a live operating system that you can boot from USB or DVD. The intentions of this project are to assist users in preserving their privacy and anonymity when you wish to circumvent censorship, leave no trace, or use cryptographic tools. The tails project

How does TAILS Work

TAILS is a live operating system. This means it is a complete bootable computer installation that can run off of CD-ROM, USB, or similar means. There are many operating systems that allow you to boot from USB and run the OS without causing changes to the host computer. However, the real claim to fame that TAILS has is the deep integration with TOR and the bundled availablity of the TOR Browser. TAILS previously offered I2P as an alternative to TOR but removed this capability due to difficulty with finding maintainers for the I2P component of the project and the rapid pace in which vulnerabilities are found.

You can easily build a live operating system from any number of linux distributions and could theoretically install TOR as a component of that OS. If you feel confident in setting up an operating system and installing TOR, I believe it would make some sense to roll your own. If you are not confident then you should look at tools like TAILS to provide a ready made solution that provides some reasonable levels of privacy.

How To Install

You can choose to install TAILS using two methods. One method would be to install the OS on a thumb drive or CD. This method is simple and is the expected method of deployment.

Method One

  1. Get Etcher

  2. Download TAILS

  3. Burn the OS to a USB drive using Etcher

Method Two

  1. Download TAILS

  2. Create a virtual machine with no hard drive

  3. Boot from the ISO into a virtual machine

How To Setup

TAILS is relatively simple to use and requires little or no setup. TOR is set to activate on boot and you can begin surfing the web shortly after you gain access to the OS and connect to a wireless network or hard wired network. The purpose of using something like TAILS is to give you a basic and relatively safe method of working with TOR with a reasonable amount of security.

Why use TAILS

When you want to enhance security and privacy while reducing the chance that forensic analysts will be able to recover your information from the system you were using.

How to secure your thumb drive

Don’t loose it. Don’t allow others to grab it.

Is TAILS fool proof

No. TAILS is a simplified method of deploying TOR on a computer while greatly reducing your local foot print. Is it fool proof? Absolutely not. Your online activity is relatively obvious and your use of TAILS does raise red flags. You should not expect TAILS to provide any aditional protection over a local copy of TOR unless you are ready to change your method of surfing the internet drastically.

Things to do to enhance security with TAILS

  1. Do not mix identities with TAILS

  2. Do not use TAILS or TOR from your home network

  3. Do not use compromised hardware

  4. Do not expect privacy from nation state level attacks

  5. No software is perfect

  6. Your VPN may be connected to you by your payment method

Answers

  1. TAILS OS is an Amnesic Operating System used to provide privacy anonymity.

  2. TAILS provides an easy to use copy of Tor and includes many tools that may be useful to someone wishing to surf the internet using Tor.

  3. TAILS OS is an operating system that is programmed with a number of tools that allow users to connect to the internet over Tor without saving any information to a hard drive for later retrieval.

  4. TAILS OS is normally installed on a USB thumb drive as a ‘live’ operating system.

  5. TAILS OS has and does sometimes suffer from 0-Day exploits and this has caused much debate on when and how these issues should be reported.

Conclusion

TAILS is a great tool for individuals who do not have the technical skills necessary or the time to setup and deploy TOR securely. You can use TAILS in combination with good operational security and smart behavior to provide maximum levels of anonymity online.

Final Recommendations

  1. Use Linux.

  2. Use Freenet.

  3. Contribute to a privacy enhancing project. I recommend Freenet. Pick one.

  4. Develop relationships and build your own ‘Darknet’. Network in the real world.

  5. Contribute to Open Source Projects.