You’re being watched.

Every week we hear on the news about data breaches exposing our passwords and our information being shared with advertisers and other organizations. We know that Google, Facebook, and other sites track what websites we visit and what items we search for, even on other web sites. You can see this for yourself. Search for a unusual item to buy on Google or Amazon, then watch it start showing up in advertisements on web sites you visit.

These sites are tracking you and feeding information back to Google via their Ad Sense system. Most ads on web sites are linked to Google and they are able to track you based on your IP address, web site logins, and web cookies. They even can use ‘fingerprinting’ of the unique characteristics of your web browser configuration to identify you. You can see your fingerprint here.

Currently, this tracking is mainly used to provide advertising to us, but there is evidence the NSA and other government agencies are collecting this information for investigative reasons. While it’s not expected the government will use your browsing history against you any time soon, it’s possible a disgruntled government agent could leak your information to groups against your way of life.

What is Tails?

To hide our computer’s fingerprint, we need to setup a generic computer with a generic web browser that shares minimal information that is the same as many others. All data on the computer and all web traffic must be encrypted to prevent eavesdropping. The Amnesic Incognito Live System, or Tails, does this.

Tails is a small operating system used from a DVD or USB stick that you boot on any computer. It has basic communications tools such as a web browser, an email client, a office suite, instant messaging, a password manager, and others.

“Tails is a live system that aims to preserve your privacy and anonymity. It helps you to use the Internet anonymously and circumvent censorship almost anywhere you go and on any computer but leaving no trace unless you ask it to explicitly.” –About Tails web page

Tails is amnesic in that it does not remember information between uses unless you specifically save the information. There are no hidden cookies or malware stored on your computer. Tails uses a read only “live” system that is clean and fresh each time you run the system. It does have a encrypted storage so you can save files and some configuration information (like passwords, email server information, and web bookmarks) between uses. This persistent storage is only available if you enter the password at the start of using the system.

Tails is incognito. Your identity is kept confidential. Tails disguises parts of your web fingerprint and uses the same values as every other Tails users. A quick check shows my Tails fingerprint matches 85,000 other users. Tails also routes all traffic through Tor. Tor is a protocol that uses layered encryption to hide who you are and where you are going. Your ISP won’t know where you are going and the destination website won’t have your home IP address in their logs.

How to use Tails

Tails is simple to use. When you boot the Tails USB drive, it will first prompt you to modify options and most importantly, enter the password for the encrypted storage. Once Tails is fully started, you will need to connect the computer to a network if it’s not already connected. Tails will then start to synchronize the clock and establish a Tor network connection. When the connection is complete, a message “Tor is ready” will appear. Your Tails workstation is secure and ready to use.

The most common use is web browsing. The Tor browser can access normal websites while protecting your identity and location. The Tor browser can also access the ‘darkweb’ sites. These are Tor protocol only sites that have ‘.onion’ at the end of their address instead of .com or .net. Tails also has the Thunderbird email client with Enigmail. This will allow you to setup encrypted communications over email.

Tails is great when you’re traveling. You can borrow any computer, reboot it into Tails and have a secure, private workstation to use with all your saved information.

Tails provides privacy and anonymity, but it does not completely hide you. Your ISP or network administrator knows you are using Tor. They can see the Tor tunnel, but can’t see your data or tell where you are visiting. At the other end of your connection, the internet site you are visiting can know you are coming from a Tor ‘exit node”. They know the computer that connects to them and they can check it against a Tor exit node list. But, the site doesn’t know your home location. And lastly, the Tor exit node can see your data if your traffic to the internet site isn’t encrypted using ssl/https for web or pgp for email.

Building a TAILS USB drive

Building your own Tails USB drive is easy. You will need one or two 8 GB USB sticks depending on the method used. I recommend 16 or 32 GB USB 3.0 sticks if you plan to store data on your Tails drive. There are two ways to create your Tails stick – Cloning or Installing. Detailed step-by-step instructions are at the Tails Download and Install page.

First way is clone a friend’s. Find someone you trust that has a Tails USB stick and clone theirs. The tails cloning will copy over the Tail operating system but not their encrypted storage. After you finish setting up your encrypted storage you can share and verify each other’s PGP email encryption keys.

The other way is to install it by yourself. This method requires two USB sticks. You’ll need to download the Tails disk from the Tails website and then install it to a intermediary USB stick. It’s not possible to create a working Tails disk from windows, so we create an intermediary drive as a go-between. Once you have the intermediary stick booted, you install Tails to the final stick by cloning the intermediary. After cloning, boot off the new final stick and configure your encrypted storage.

Take Action

As I mentioned above, Tails is not 100% private. Your internet provider or other network administrator will know you are using it. There’s a case a few years ago that illustrates this well. Someone sent a bomb threat to a college. The network administrators noted that the threat was made from a Tor exit node. Since the threat was very specific, they figured a student submitted it. Looking at their network logs, they noticed only one student using Tor at the time of the threat. They couldn’t tell for sure it was this student, but they investigated him anyway. The student ended up confessing to the threat to get out of an exam. This student was found because he stood out as the only Tor user. So, the best way to hide Tails usage is to increase Tor and Tails usage from yourself and others. Your goal is to be a needle in a pile of needles.

Learn how to setup the software on your new Tails stick in TAILS, Part 2: Setting Up Persistence.

About the author

Chad “Chainsaw” Sawyer is a information security professional that focuses on helping organizations and individuals maintain their privacy and computer data security. He’s the author of the Linux Workstation guide and blogs on privacy issues at Chainsaw’s Privacy. He holds a General Amateur Radio license and is a AmRRON Corps member.

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