Originally Posted 2025-02-04 on ejectdrive.com

Introduction to Tails

What is Tails?

Tails is designed to help you use the Internet anonymously and get around censorship. It lets you connect to the Internet using virtually any computer while leaving no trace of your activities after you have finished. Tails connects to the hardware of a computer but doesn’t use the operating system or disk drives. That means there is no permanent record of your activities on that computer. Once you remove the Tails USB Stick or DVD and restart the computer, there will be no way to tell Tails was used there. Tails is far safer than the typical operating system, but it is not foolproof. [3]

How good is this really?

Tails and the Tor project were developed by the US Government for secure espionage. They realized that if they only used it themselves, everyone would be able to tell who was government and who wasn't. In order to keep it secure for their own use, they were forced to release it publicly and keep it secure for everyone to use. The US Goverment is still the primary financial backer of Tails and the Tor project.

If you follow the instructions provided by Tails, people will know that someone is using it, but they won't be able to tell who.

Advantages

Use almost any computer, including those owned by other people.
Leave no trace on the computer when you are done.
Save important files, emails, and bookmarks to persistent storage on the Tails drive. [1]

What disappears?

Websites that you visited.
Passwords that you typed.
Networks and WiFi that you connected to. [1]

Tails is safe, but not magic

Files you share may still have date, time, location, and device information.
Using Tails for more than one purpose at a time may reveal your identity.
Tails cannot hide that you are using Tails and Tor from sites you connect to.
Tails may not hide your communications from skilled, determined attackers.
If you use a computer which is compromised, your security may be as well. [2]

Starting Tails

This document assumes that you have been provided with a copy of Tails on a USB Drive.

For the best security, do not plug in your Tails USB stick while another operating system is running on the computer. [5]

Use your Tails USB stick only to run Tails. Do not use your Tails USB stick to transfer files to or from another operating system. [5]

Getting into Tails can be tricky. The two primary methods are from inside Windows, or using the computer's Boot Menu key.

Booting the Tails USB from Windows

https://tails.net/install/windows/index.en.html#restart

Log into Windows normally.
Insert the Tails USB.
Click on the Start Button.
Press and hold the Shift key while you choose Power > Restart.
In the Choose an option screen, choose Use a device.
In the Use a device screen, choose Boot Menu.

Windows will shut down, reboot, and you should have options of possible boot devices.

In the Boot Menu, select your USB stick and press Enter.
If the computer starts on Tails, the Boot Loader appears and Tails starts automatically after 4 seconds.

The Troubleshooting Mode entry disables some features and might work better on some computers.
The External Hard Disk entry makes it possible to start from some problematic USB sticks.

Booting the Tails USB without access to Windows

https://tails.net/doc/first_steps/start/pc/index.en.html#boot-menu-key

Troubleshooting Tails not starting at all

https://tails.net/doc/first_steps/start/pc/index.en.html#not-entirely

Using Tails

It's best not to label the drive in any way. If you think someone could take it off you, destroy it.
It's recommended that you use Tails on public WiFi or in a Public Space, like a Library or Internet Cafe.
You may also be able to use the Library's computers instead of your own computer, which provides an additional layer of security.
Leave your phone at home if it's safe to do so. See "Turn off your phone!" in the Additional Resources for more advice.
Use Tails sessions for only one purpose at a time. [4]
Use a password manager to paste saved passwords. This way, you don't have to type passwords that might be visible to people or cameras near you. [5]
Use the screen keyboard, if you are using a public computer or worry that the computer might have a keylogger. [5]
If someone interrupts you while using Tails (or tries to arrest you) immediately unplug the Tails Drive and unplug the computer or turn it off. Destroy the Tails drive if possible.

Welcome Screen

When Tails first starts, the welcome screen allows you to select:

The Language
The Keyboard Format
Whether Persistent storage is enabled

As well as other optional settings. For Users in the US, the default Language and format options will suffice. Click Start Tails to move to the next section.

Create Persistent Storage only if you need to save files to the flash drive. If someone gets hold of the drive, they could reverse the enryption and access the files.
Set an Administration Password to be able to perform administrative tasks like installing additional software or accessing the internal hard disks of the computer. [7]
Turn on the Offline Mode if you want to work completely offline for increased security. [7]

Desktop Environment

When Tails Loads, you will be presented with a Desktop Computer environment that you can do your work in. Familiarize yourself with the location of the following:

Activities: Your Windows and Applications. You can search here as well.
Applications: All of the included and installed software.
Places: Shortcuts to commonly used folders and applications.
System Menu: In the Top Right. Allows you to manage your settings, connect to a Wi-Fi network, and restart your computer.

Included Software

Tor Browser: Along with the "Tor Connection" application, creates the heart of the Tails experience. Allows you to browse the web anonymously and uncensored.
Tor Connection: Allows you to connect to the Tor network.
Persistent Storage: Allows you to save some of your files and configuration in an encrypted Persistent Storage on your Tails USB stick.
Tails Documentation: Opens an offline version of the Tails website and documentation.
Thunderbird: Allows you to write emails and read RSS and Atom feeds.
KeePassXC: Allows you to store and manage secure passwords.
Kleopatra: Allows you to encrypt text and files using GnuPG.

As well as other applications for specific purposes. The Tails Documentation contains more details on how to use each of these applications to best secure your online experience.

Using the Tor Browser

The Tor Browser is the core of the Tails experience. Tor uses what is called "Onion Routing" to pass your information through multiple servers, encrypting it at each step. This ensures that almost anyone watching it can't see what you're doing, only that you're using Tor.

It's important to note that any site you connect to can absolutely still see what you're doing. Just because your connection to social media is very secure, it doesn't mean that you can trust the social media site to keep you private.

Don't sign into any websites you connect to.
Don't provide your name, email, home address, phone number, or any other identifying information.
Don't use a VPN with Tor.
Don't torrent files on Tor. Use a VPN instead.
Don't install browser plugins, including adblock.
Don't open downloaded documents while connected to the network.

What is a .onion?

Onion services allow people to browse and publish anonymously, including publishing anonymous websites. Some Onion services include:

Chat
File Sharing
More secure versions of everyday websites.

Websites that are only available over Tor are called "Onions" and end in .onion. Onion Sites and Services are not indexed in search engines, and can be hard to find. Onion Services hosted by the Tor Project can be found at onion.torproject.org.

Tor, Onion Services, and the Dark Web

You may have heard that Tor is "The Dark Web". This is ostensibly true. Some definitions are helpful here:

The Surface Web: This is anything you can find on Google or Bing. Social media, news sites, anything you can find with the right search terms.
The Deep Web: This is anything on the regular internet, but you can't search. Pages that require you to be logged in. The contents of your Cloud Storage drive. Companies internal websites for employees. The results of interactions with a website.
The Dark Web: Anything accessible only through an "overlay network" like Tor. These sites and their connections are usually encrypted, and run anonymously. These are .onion sites and services.

Because of the hidden nature of the Dark Web, there is a significant amount of crime that takes place. However, if a government entity identifies a Dark Web site, it can still be shut down and prosecuted. Users of the site, if they can be identified, can also face legal action. 56.8% of known Dark Web sites are considered "Illicit" or promote illegal activity.

Despite that, there are legitimate uses for the Dark Web. These include:

Social Justice
Investigative Journalism
Private Communications

Don't let the fear mongering scare you. Using Tor to access The Dark Web is not illegal (in the US). Only doing Illegal things with it is. As long as you know your rights, operate within the law, and keep yourself anonymous, you will be fine.

Additional Digital Security Resources

Protect yourself from "Doxxing"
UC Berkeley
https://oercs.berkeley.edu/privacy/privacy-resources/protect-yourself-doxxing

Turn off your phone! And other basic digital security strategies.
https://ia802707.us.archive.org/12/items/zines-security/Turn_Off_Your_Phone.pdf

Surveillance Self-Defense
Electronic Frontier Foundation
https://ssd.eff.org/

What do you need to protect?
security in-a-box
https://securityinabox.org/en/

Sources

[1]

"How Tails works"
https://tails.net/about/index.en.html

[2]

"Warnings: Tails is safe but not magic!"
https://tails.net/doc/about/warnings/index.en.html

[3]

"Tails OS – An Actionable Guide for Regular Folks"
Bill Mann, blokt.com
https://blokt.com/guides/tails-os

An Introduction to Tails OS