Anonymity & Privacy

Living off the grid with TAILS OS ๐Ÿ‘ป

TAILS OS can be a hacker’s best friend, allowing for completely anonymous activity on the move. In this guide, I’ll explain what TAILS is, how it works, and how you can use it to maximise your online privacy.

There are private operating systems โ€” and then there’s TAILS. It’s so private that merely searching for it on Google can raise eyebrows at the NSA (we know this from the Snowden leaks). 

TAILS, short for The Amnesic Incognito Live System, stands as perhaps the most private OS in existence. It’s the top choice for whistleblowers, journalists, individuals facing domestic abuse, and even intelligence agents operating in hostile environments. 

But what exactly is TAILS, and does it live up to the hype? Who uses it, and how can it improve your privacy? In this concise tutorial, I’ll delve into why I hold TAILS in high regard and address these questions comprehensively.

I will start by explaining what TAILS is and the situations where it can come in handy. We will then explore how TAILS can be used to help you go off the digital grid, free from the predatory eyes of both marketers, tabloid journalists, and the mass surveillance courtesy of the NSA and GCHQ.

If you look at the way post-2013 whistleblowers have been caught, it is clear the absolute most important thing you can do to maintain your anonymity is reduce the number of places in your operational activity where you can make mistakes. Tor and Tails still do precisely that.

What is TAILS and how does it work?

TAILS, short for The Amnesic Incognito Live System, is a privacy-focused operating system designed to preserve anonymity and secure communications.

It operates as a live operating system, meaning it runs directly from a USB stick or DVD without the need for installation on a computer’s hard drive. TAILS routes all internet traffic through the Tor network, which encrypts and anonymises data, making it difficult for third parties to track users’ online activities.

Additionally, TAILS is configured to leave no trace of user activity on the host system, employing features such as RAM memory wiping and data encryption to enhance privacy.

TAILS routes all your traffic through the TOR network

TAILS directs all internet traffic through the Tor network, a decentralised system that anonymises data by passing it through a chain of encrypted nodes. This process shields the user’s IP address and browsing activity, bolstering online privacy and security.

For instance, if I were located in the Scottish Highlands and using TAILS, my traffic might traverse servers (or relays) in France, then Switzerland, and finally the Netherlands before reaching the desired website. Consequently, the website administrator would only see the last IP address (in the Netherlands) and would be unable to pinpoint the traffic’s origin. Similarly, my Internet Service Provider (ISP), such as BT or Virgin Media, would merely detect that I’m connected to a server in France, without knowledge of the specific websites I visit.

It’s this multi-step routing, known as Onion Routing, that renders TAILS a potent tool for anonymisation in a hacker’s toolkit.

TAILS offers significantly greater security compared to relying solely on the TOR Browser. With TAILS, all traffic is channeled through the TOR network, preventing rogue background tasks from exposing your actual IP address during internet browsing.

While the Tor network grants access to certain segments of the Dark Web, it’s essential to understand that TAILS itself does not target Dark Web traffic. Rather, it furnishes a platform for users to surf the internet anonymously and securely, shielding their online identities from surveillance and tracking.

TAILS is built with counter-forensics in mind

Using TAILS instead of relying solely on a standalone TOR Browser within a conventional Linux distributionโ€”or worse, attempting to run TAILS on a Windows or Mac systemโ€”offers a distinct advantage: TAILS is meticulously crafted with counter-forensics capabilities.

In practical terms, this signifies that even if an adversary were to gain access to your computer and subject it to forensic analysis, they would encounter minimal traces of your activities conducted within TAILS.

TAILS earns its name “amnesic” for a reasonโ€”it forgets everything you’ve done on your computer as soon as the power is cut.

How do I install & run TAILS?

There are many more benefits and features to TAILS in addition to what I listed above – but let’s cut to the chase and I will explain how you can attain privacy & anonymity with TAILS for yourself. I will explain how to install TAILS through a Windows computer, as most of my readers use Windows. The process is much the same for MAC & Linux users.ย 

You will need a USB stick to install TAILS – its mandatory as TAILS is booted from a USB.

Step one: Download TAILS

Before you even consider searching for TAILS on a search engine such as DuckDuckGo, I highly recommend – although this is not compulsory – turning on your VPN and enabling the killswitch. If you don’t know what a VPN is, you can read this article I wrote on the matter. VPNs are definitely not perfect – but it is better than nothing.ย 

Next, go to the official TAILS website and navigate to the download section. It is important that you download TAILS from a trusted source to ensure there have been no backdoors included with your installation.ย ย 

You can download TAILS by clicking on the button below.

Installing TAILS Guide - after downloading TAILS, you will see it contained within your Downloads folder.

Sidenote: it is considered best practice to verify your download to make sure that it is safe and was not intercepted and corrupted during the download process. You can do this by uploading your ISO image to the TAILS installation page, or by clicking here and scrolling to step two.

Step two: Install Balena Etcher - a user-friendly way to create bootable USBs

After you have downloaded TAILS, the next step is to create a bootable USB stick with our TAILS OS on it. To do so, we will install BalenaEtcher – software that allows you to flash an operating system to a USB stick in a few simple steps.

Click on the button below to begin downloading Etcher – it will take just a few minutes. After doing so, click on the download within the downloads folder and follow the installation process. Again, its a simple process and will be completed within a few minutes.

Step Three: Flash TAILS to the USB

Flashing TAILS to your USB stick

After installing BalenaEtcher, the next step is to flash TAILS onto the USB drive. This process involves plugging in your USB stick, selecting the TAILS image file you downloaded and specifying the USB drive as the target. Once you’ve confirmed the settings, simply click on the “Flash” button, and Balena Etcher will proceed to write the TAILS image onto the USB drive.

This may take a few minutes depending on the speed of your computer and the USB drive. Once the flashing process is complete, you’ll be ready to use your newly created TAILS USB drive for enhanced privacy and security.

And that’s all there is to it! You now have TAILS installed on your USB stick, and all you have to do now is plug it into your computer, boot it, and begin using TAILS.

How to use TAILS safely

Do not use TAILS for any illegal activity. Aitken Security does not condone using the information contained within this guide for criminal activities. Remember: THINK before you TYPE.

Before I begin explaining how to use TAILS for the first time, I should explain my three golden rules for using TAILS. Whilst TAILS is probably the most private Operating System we have, its not a complete solution, and most of the weaknesses in TAILS are caused by human error. My three rules are not extensive, but they are a good starting point.

Rule one: NEVER log in to an account that is tied to your real identity.

It’s paramount to safeguard your real identity while using TAILS. Never log in to any accounts tied to your real name or personal information. In other words, don’t log in to your Facebook or Google account whilst using TAILS – it will instantly deanonymise you. This practice ensures that your online activities remain anonymous, shielding you from potential tracking or surveillance efforts.

Rule Two: Practice OPSEC, or Operational Security

Operational security is key to staying secure while using TAILS. This involves implementing measures like using screen dimmers to prevent shoulder surfing and ensuring that no sensitive information is inadvertently revealed. Use TAILS at an internet cafe instead of at your home address, whilst being cautious to avoid sitting in view of any CCTV cameras that can record your screen. By staying vigilant and employing these tactics, you can enhance your overall security posture and mitigate potential risks.

Rule Three: Disconnect After Use

After completing your tasks with TAILS, it’s essential to disconnect from the system and shut down your device. This step ensures that no residual data or traces of your activities are left behind, minimising the risk of unauthorised access or compromise. By disconnecting after each use, you maintain control over your privacy and protect yourself from potential threats

Booting TAILS for the first time

Booting TAILS for the first time marks a pivotal moment in your journey towards bolstering your online privacy and security. As you embark on this process, there are several key steps to follow.

Once your USB drive is prepared, insert it into your computer and restart the system. Access the boot menu or BIOS settings to designate the USB drive as the primary boot device. This step ensures that your computer boots directly from the TAILS USB drive, instead of your standard operating system such as Windows.

This part may cause some issues for new users – if so, you should drop me a DM on my Instagram account @aitkensecurity and I will happily assist you.

Upon booting from the USB drive, you’ll encounter the TAILS Greeter interface. Here, you’ll have the opportunity to configure various settings according to your preferences. These settings may include language selection, keyboard layout, and additional options tailored to your specific needs.

One of the most distinctive features of TAILS is its integration with the Tor network. TAILS automatically routes all internet traffic through Tor, providing users with enhanced anonymity and security online. You can establish a connection to the Tor network directly from the TAILS Greeter interface. You will notice that websites may appear in a foreign language – such as Dutch or German – and this is because your IP will correspond to that of a foreign country.

Once configured, you’ll find yourself logged into the TAILS desktop environment. Take some time to explore the various applications and features included in TAILS. The Tor Browser, for example, enables anonymous web browsing, while encrypted messaging clients offer secure communication channels.

The TAILS OS Homepage. On the top left, you will see a tonne of useful covert tools for safe browsing and communcations.

TAILS is packed with useful counter-surveillance and covert communication tools

TAILS comes pre-installed with a range of applications tailored to enhance privacy, security, and anonymity. Some notable ones include:

  • Tor Browser: The cornerstone of TAILS, Tor Browser allows users to browse the internet anonymously by routing traffic through the Tor network, obscuring their IP address and online activity.


  • Encrypted Email Client: TAILS includes an encrypted email client, typically Mozilla Thunderbird with the Enigmail extension, enabling users to send and receive emails securely using PGP encryption.


  • Secure Instant Messaging: To facilitate secure communication, TAILS may include instant messaging applications like Pidgin with OTR (Off-the-Record Messaging) encryption or Ricochet, a decentralised, peer-to-peer instant messaging platform.


  • LibreOffice: For productivity needs, TAILS provides LibreOffice, a suite of office applications including word processing, spreadsheets, and presentations, ensuring users can work on documents securely.


  • GnuPG: TAILS often includes GnuPG (GNU Privacy Guard) for encrypting and decrypting files and communications, adding an extra layer of security to sensitive data.


  • KeePassXC: To manage passwords securely, TAILS may feature KeePassXC, an open-source password manager that stores passwords in an encrypted database.


  • OnionShare: For secure file sharing, OnionShare allows users to anonymously share files over the Tor network without relying on third-party services.


These applications, combined with TAILS’ built-in security features and anonymity-preserving mechanisms, offer users a comprehensive toolkit for navigating the internet while prioritizing privacy and security.

Conclusion: Living Off The Grid with TAILS

In conclusion, utilising TAILS provides a powerful toolset for living off the grid, ensuring privacy, security, and anonymity in today’s digital world.

By adhering to the rules of protecting one’s identity, maintaining operational security, and disconnecting after use, users can navigate the digital landscape with confidence, free from the constraints of traditional surveillance and tracking mechanisms.

TAILS empowers individuals to reclaim control over their online presence, enabling them to communicate, browse, and transact with peace of mind, knowing that their activities remain private and secure. Whether evading censorship, safeguarding against surveillance, or simply seeking to preserve digital autonomy, TAILS offers a robust platform for those seeking to live off the grid in a digital age.

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