Navigating in the Shadow: Anonymity with Tails

In an increasingly surveilled digital landscape, the desire for online anonymity has increased. Tails, or The Amnesic Incognito Live System, has emerged as a powerful tool for those seeking to protect their privacy. This article explores the core principles of Tails and how it facilitates anonymous online activity.

What is Tails?

Tails is as a self-contained, live operating system, designed for running from a USB drive (or DVD :D), transforming any computer into a privacy-focused workstation. Unlike traditional operating systems that install to a hard drive, Tails executes entirely within the computer’s RAM. This design choice ensures that no persistent data is written to your computer storage devices. More important, each reboot restores the system to its initial state, effectively deleting any traces of previous usage. So, upon a normal shutdown, all data held within the RAM is automatically erased. Furthermore, even a detachment of the USB drive triggers an immediate overwrite of the RAM, effectively scrambling and eliminating any residual data (critically for security). This “amnesic” characteristic, provides a robust defense against forensic data recovery, ensuring that your activities remain confidential and untraceable.

Key Features for Anonymity:

So, how does Tails actually keep you anonymous? It’s not magic, it’s a smart combination of tools and the way it’s built. Let’s break down the main things it does:

• Tor Integration: Tails forces all internet traffic through the Tor network. Tor routes your connection through multiple relays, obscuring your IP address and making it extremely difficult to trace your online activities back to you.

• Amnesic Nature: As mentioned, Tails leaves no persistent data on the host computer. This prevents forensic analysis and ensures that your activities remain confidential.

• Cryptographic Tools: Tails comes pre-installed with a suite of cryptographic tools, including: GnuPG: For encrypting and signing emails and files and OnionShare: For securely sharing files over the Tor network.

• Software Selection: Tails includes a curated selection of privacy-focused applications, such as the Tor Browser, Thunderbird, and Pidgin. This reduces the risk of using software that might compromise your anonymity. Read more from the official website

• Security Hardening: Tails is designed with security in mind. It disables potentially vulnerable features and applies security patches promptly.

• Mac Randomization: Tails spoofs the mac address by default, you don‘t have to configure anything!

Persistent Storage

While Tails is designed to be amnesic, completely erasing data after each session, it also offers a feature called Persistent Storage for users who need to save specific files and settings. This optional, encrypted partition live on the same Tails USB drive, allowing you to retain sensitive information across reboots. When you start Tails, you’ll be prompted to unlock this Persistent Storage with a password you set during its initial creation.

Tails utilizes LUKS (Linux disk encryption standard), to secure this storage. LUKS encrypts the entire partition, making it virtually impossible to access the contents without the correct password. This provides a secure way to store documents, browser bookmarks, or other essential files while still maintaining a high level of privacy. Remember that the security of your Persistent Storage depends on the strength of your password.

Get Start with Tails:

To get started with Tails you’ll need a >8GB USB drive. Once you’ve downloaded tails from the website, checked the signature and created the bootable USB, simply restart your computer and tell it to boot from the USB drive.When you boot Tails for the first time, you’ll be greeted with the Tails Greeter. This initial screen allows you to configure some basic settings before you dive into the anonymous environment. You can choose your language and keyboard layout, ensuring comfortable use. Critically, this is also where you’ll have the option to set up Persistent Storage. If you plan to save files or settings across sessions, you’ll want to create and unlock this encrypted storage here. Otherwise, by default, Tails will start in its amnesic mode, leaving no trace. After making your selections, click ‘Start Tails’, and you’ll be launched into the secure operating system, ready for private browsing.

Circunvent Censorship

For users in regions with heavily restricted internet access, or where Tor is actively blocked, Tails offers obfs4 bridges. These bridges act as obfuscation layers, masking Tor traffic to resemble normal internet communication. By using obfs4, you can bypass censorship and connect to the Tor network even when it’s being actively filtered. To utilize these bridges, you’ll need to configure them within the Tor Connection settings during Tails startup. This adds an extra layer of protection, making it significantly harder for censors to detect and block your Tor connection, ensuring access to a free and open internet. You can request these bridges from the Tor Project website, through the Tor Browser itself, or by sending an email request. Beside bridges, it is also possible to configure vpn to wrap the tor traffic, but I do not recommend it since every missconfiguration will expose your real identity and thus I will not discuss it.

Important Considerations on Maintaining Your Anonymity

While Tails offers a powerful shield for your online privacy, it’s vital to recognize that it’s not an impenetrable fortress. There are two main techniques that your enemies use to crumble your anonymity: correlation timing attacks and browser fingerprinting.

Correlation timing attacks analyze patterns in your internet traffic, matching the timing of your actions on the Tor network’s entry and exit points. If an adversary controls enough points, they can correlate your traffic and potentially expose your real IP. Imagine a burst of data leaving your PC and entering Tor. If, almost instantly, a matching burst of data comes out of Tor and heads straight to evil.com, it’s very probable that the data originated from you, revealing your connection.

Browser fingerprinting track unique characteristics of your web browser. Websites can gather a surprising amount of information, like the specific fonts installed on your system, the exact version of your operating system, the plugins you’ve enabled, and even the tiny differences in how your browser renders graphics. When combined, these seemingly minor details create a unique ‘fingerprint’ that can be used to identify you, even if you’re using Tor or a VPN. For example, two users might both have Firefox, but their installed fonts or screen resolutions could differ, creating distinct fingerprints. Websites can also use JavaScript to probe your system for more detailed information, such as your timezone, language preferences, and the capabilities of your graphics card. Each piece of information adds to the uniqueness of your fingerprint, and in this case you do not want to be unique. This is why you should never maximize the Tor Browser window to full screen or enable javascript, as this can reveal your screen resolution or more info that contribute to a more unique fingerprint. In this case you want to keep everything as standard as possible.

Beside those attacks there are numerous more factors, both technical and behavioral, can expose your identity if not carefully managed.

• Operational Security Mistakes (OpSec): Anonymity is as much about your actions as it is about the tools you use. Careless online behavior, such as revealing personal details, using consistent usernames across platforms, or clicking on suspicious links, can unravel your anonymity. Weak or reused passwords, even with encryption, are a significant vulnerability. Remember, your online persona must remain consistent with anonymity.

• Tor’s Potential Weaknesses: Though Tor provides a robust layer of anonymity, it’s not infallible. Sophisticated adversaries with substantial resources, such as state-sponsored actors, might employ traffic analysis or other advanced techniques to correlate your Tor activity with your real identity. Additionally, vulnerabilities within the Tor network itself, however rare, can be exploited.

• Software Update Negligence: Tails, like any software, requires regular updates to patch security vulnerabilities. Failing to keep your system updated leaves you susceptible to known exploits, potentially revealing your IP address or other identifying information. Delaying updates is like leaving a door unlocked.

• Persistent Storage Misuse: While Persistent Storage offers convenience, it introduces potential risks. If the passphrase is weak, or if the storage is not properly configured, it can become a point of vulnerability. Moreover, storing sensitive data on a USB drive that could be lost or stolen presents a physical security risk. Inadvertently storing identifying information in the persistent storage, defeats the purpose of anonymity.

• Malware and Exploits: Although Tails is designed to be secure, malware or exploits targeting vulnerabilities in the operating system or applications can compromise your anonymity. Be cautious about downloading files or visiting untrusted websites, even within Tails.

• Human Error: The most common way anonymity is broken is by human mistake. Sending unencrypted information, revealing personal information in an online form, or simply failing to follow best practices can undermine all other security measures.

Conclusion:

Tails offers a powerful and seriously strong setup for staying hidden online . It combines Tor integration, an amnesic design, and a suite of cryptographic tools, that provides a solid foundation for protecting your privacy. However, it’s essential to remember that anonymity is a complex issue, and Tails is just one tool in a larger arsenal. Responsible use and a strong understanding of operational security are crucial for maintaining true anonymity. It’s important to note that there are other robust solutions like Qubes OS, which offer different approaches to security and privacy, but i will try to touch on those in a separate article.

As always I hope you enjoy this article!