You run the Tails OS if you want privacy, security, and anonymity. But for a more interesting review, let’s start with a story … one that involves a little adventure and travel to a beautiful country that’s, unfortunately, openly hostile to privacy.
A Story About Privacy: ‘Tis the Season for Giving
Imagine you’re about to leave on a trip overseas. To China, in fact!
You’ve wanted to see Beijing since childhood.
You think to yourself … great culture, amazing food, and a thousand-year-old history are finally within reach!
So you make all the proper preparations.
And because you don’t like to take risks, you get a head start and catch an early Uber. Those lines at the airport security checkpoints are predictably long so you’re not taking any chances!
You’ve brought your laptop too, and with it, all the goodies — your personal pictures, spreadsheets with passwords, private email, internet bookmarks (and cookies and browser history too)!
Sure you didn’t need to bring all of this, but time is of the essence!
Gotta go, gotta go!
And it’s Christmas after all, ’tis the season for giving! What could go wrong?
When you arrive in Beijing, you marvel at the beauty of the world-class airport. It’s huge! And filled with life! And everyone seems to love foreigners!
So much so that when you get to the Visa checkpoint, you’re treated like a VIP.
Lucky you, they want an interview!
“Just leave your belongings over there ma’am,” says the nice officer. “We’ll be sure to take reeeeeal good care of them,” he adds.
But you’re not so sure about this. You want physical access to your laptop at all times. It’s expensive and contains sensitive personal information. So you respectfully protest …
The officer, without hesitation, repeats himself … this time a little more sternly, “Ma’am, it’s an airport security policy that we inspect all suspicious luggage.”
Having no other options you begrudgingly comply.
What you may not be aware of is that while you’re being peppered with seemingly innocent questions, a forensics expert is copying your hard drive … every last bit — even the files you deleted!
This could so easily have been avoided. If only you had known …
This article provides an overview of the Tails operating system (OS), a memory-resident OS that leaves-no-trace of your internet activity and which provides optional full disk encryption for enhanced security.
More specifically, this means that after running the Tails OS — from any computer, be it a laptop or a desktop — subsequent examinations of the local computer’s hard drive would show no evidence of your activity. It would be as if you hadn’t used the computer at all.
Tails is bringing privacy back!
The times are a-changin’ my friends and so should you!
By the end of this article, you’ll understand how the Tails OS works, how to install it, and how you’ll be more secure from using it.
What Is Tails?
In 2013, Edward Snowden, a former contractor for the National Security Agency, provided classified documents regarding U.S. government surveillance to Glenn Greenwald, an American journalist. To communicate securely, they used Tails.
Many years later, on December 13, 2017, Snowden tweeted the following message regarding Tails.
TAILS (@Tails_live, https://t.co/Re3LzE4WdO) is the most accessible for normal folks looking to “torify” non-browser traffic, and a gentle introduction to Linux (which is still gonna be a learning experience). You can boot it from a USB stick without overwriting your everyday OS. https://t.co/eHqYarXFjZ— Edward Snowden (@Snowden) December 13, 2017
From this tweet, it’s obvious that Snowden is still an enthusiast.
Tails, which stands for The Amnesic Incognito Live System, is a free “live” Linux distro built using Debian. It was designed from the ground up to be secure and to safeguard your privacy and anonymity through non-persistent storage.
In other words, nothing gets saved to disk.
Tails is designed to run on external media, like a USB flash drive, as opposed to a desktop computer or a virtual machine. This is by design for reasons we’ll discuss later.
The below screenshot taken from the Tails download-page indicates that you can install the software from Windows, macOS, or Linux.
How Do You Verify the Integrity of Your Tails OS ISO File?
Once your download is complete, it’s easy to verify its integrity — an important step before installation, which ensures the software you’re installing is genuine.
You can do so in one of the following three ways:
- With the “Tails Verification” browser extension (available for Chrome and Firefox)
- Manually with a verification key via one of the following methods:
a. Windows with Gpg4win,
b. macOS with GPGTools,
c. from within Tails,
d. using the command line), or
- With your torrent client if you downloaded Tails via a torrent file
How Long Does It Take to Install the Tails OS?
I installed the Tails OS from my macOS, and to do so, I used Etcher. Etcher is free and open-source software for writing image-files to external media (e.g. USB flash drive, DVD). This software allowed me to flash my USB device using the default Tails OS image-file.
The process in total took only a couple of minutes.
In fact, it took longer to download and install Etcher than it did to flash my USB device with the Tails OS image.
The below screen capture is of Etcher. As you can see, the software couldn’t be simpler.
How to Use Tails?
All internet-accessible software within the Tails OS distro is preconfigured to connect through Tor.
And this is no small thing.
Getting Tor configured correctly is paramount for privacy as Tor wraps a layer of security around your internet communications.
In other words, Tor prevents the places you visit online from learning your physical location, your IP address, and, in some cases, your internet activity. Critically important stuff for privacy.
The Tails OS also comes with a number of preinstalled programs:
- Pidgin preconfigured with OTR (Off-the-Record messaging)
- OnionShare for anonymous filesharing
- Thunderbird with Enigmail for OpenPGP support
- Aircrack-ng for wireless network auditing
- Electrum, an easy-to-use bitcoin client
But the most important aspect of Tails is how it runs.
The Tails OS uses the host computer’s random access memory, or RAM, as temporary storage space to run core system services. It doesn’t access or modify the hard drive of the computer on which it’s running.
Remember, with Tails you’re booting with a USB flash drive so you’re bypassing the host operating system entirely.
This means that when the computer is shut down so too are all traces of prior activity. There’s literally no digital footprint as all RAM is cleared once the computer is turned off.
How Anonymous Is Tails?
The Tails OS is one of the most secure Linux distros available, offering an abundance of privacy features and software.
Some of these are: Tor, the Tor Browser, and VeraCrypt (the successor to TrueCrypt), and LUKS (Linux Unified Key Setup) for disk encryption — but they’re just the tip of the iceberg.
To ensure privacy it’s important you understand how and when to use Tails.
So let’s get to it:
It’s my recommendation as well as other infosec practitioners that you shouldn’t run Tails from a virtual machine, period. If the host is compromised, your Tails OS installation will be vulnerable to malware, man-in-the-middle (MTM) attacks, as well as keyloggers and other malicious software. This is why it’s preferred that you boot your computer using Tails from external media like a USB flash drive, which bypasses entirely the host OS.
If you’re really concerned about your privacy, I highly recommend you read more about this here.
Does Tails OS Support Disk Persistence?
With all this talk about non-persistent RAM, you may be wondering if you can save files or even bookmark webpages.
In short, persistent volumes — the means to save files — within the Tails OS are possible and easy to setup.
To do so you’ll click “Applications” from the very top left of the screen -> then “System Tools” from the submenu -> then “Configure persistent volume” to get started.
This process will create an encrypted volume on your existing USB flash drive so that any data maintained for offline safekeeping is guarded against physical access.
You’ll then be prompted to configure what you want to be stored in your newly encrypted volume, which are any of the following:
- Personal Data
- Browser Bookmarks
- Network Connections
- Additional Software
- Bitcoin Client
- SSH Client
- Dotfiles (Symlink into $HOME every file or directory found in the ‘dotfiles’ directory)
Your data will be encrypted using LUKS, which is an acronym for the Linux Unified Key Setup, a disk encryption specification. So now even if you physically lose your USB flash drive, your data will remain secure.
You can also install additional software to your persistent volume if you so choose.
To do so you’ll click again click “Applications” -> then “Tails” from the submenu -> then “Additional Software” to get started.
VeraCrypt, the successor to TrueCrypt, is now supported as well.
Should You Use the Tails OS?
The short answer is yes.
Tails is a great OS for people concerned about privacy, censorship, and security. By default, it connects through the Tor network to secure your communications. While this does slow down your connection, it also masks your online footprint.
And because the OS can be run from external media, like a USB flash drive, you can attach the media to your keychain or carry it in your pocket for physical security as well.
What I really like about Tails, though, is the peace of mind it brings me when I travel. Because the OS runs from memory, nothing changes on the physical media. This means a simple reboot will reset my host environment.
You could even install your favorite cryptocurrency wallet on a persistent partition for security-enhanced shopping.
If I were to visit a suspicious website that could compromise my desktop or laptop, running Windows, for instance, I’d have to reinstall my entire OS to feel safe, which could take hours.
Using Tails will make it difficult for Internet Service Providers to gather your data, advertisers and hostile governments to track your activity, and hackers to steal your identity.
So in conclusion, I highly recommend the Tails OS.
This is especially true if you’re traveling to a hostile country where you can’t physically protect your computer at all times, or you suspect someone may monitor your internet communications while there.
Tails is really great too because reboots entirely reset the operating system so any potential compromise(s) don’t require a time-intensive reinstall. If you get infected with any form of malware, you simply reboot and you’re ready to go again.
The Tails OS was dead simple to install using a macOS. As stated earlier, I used Etcher to flash my USB flash drive and I had zero issues.
If your operating system is Windows, the installation process is similar, meaning it’s super easy to do.
All of the software I needed was preinstalled, preconfigured and available by default, so I had instant access to Tor and a suite of tools at my disposal. I didn’t need to install anything.
And finally, I created an encrypted persistent volume using the same USB flash drive on which I was running the Tails OS, which took literally seconds to configure and enable.
I couldn’t ask for more in a free OS.