Analog vs. Digital Living: Real Solutions to Absolute Anonymity and Privacy

by DocSlow

Thirty years ago, we had no smart phones, and Tim Berners-Lee was still three years away from inventing the World Wide Web.

If we needed to research a topic, we went to the library.  Communication with friends consisted of either randomly meeting them in person (meat-space), or calling them on an analog (wired) phone to set up a meat-space meeting.  While shortwave radio communication was available, it was largely relegated to a handful of geeks, and "The Clapper" was the closest thing we had to an IoT device.

And we did just fine.

We maintained far greater security, anonymity, and privacy than anyone in today's world.  We were far more at peace with ourselves, too.  We weren't rolling out of bed and immediately accessing social media on our "smart" devices to see what our imaginary "friends" might have said while we were asleep.  We didn't sit in front of our laptops all morning in our pajamas bouncing between reading less-than-credible news websites and the latest posts of happy memes on social networks.  We got up, showered, and made breakfast.  It was a good life, and guess what?  It still exists.

Now I'm not saying that I'm an old technophobe (although I did live back when there were still rotary phones)... to the contrary, I indulge in the latest tech as much as or more than the next person.

But there is a way to balance an analog and digital lifestyle and not compromise personal security.  The more our liberties and rights are infringed upon, compromising our privacy and security, the more we we need the tools to secure such liberties.  And it doesn't mean we need to go back to the Bronze Age to do it.

In certain situations, I will use tools that are clearly an antiquated representation of our modern technology.  Yes, I'm the nutjob you've seen at the hacking conferences sporting an old flip phone and furiously typing away on my AlphaSmart 3000.  These things still work well, and afford us the comfort of knowing we're not vulnerable to the overabundance of digital hacks so prevalent today.  But when I get back to my comfort zone, I'll fire up my laptop, download the day's notes from my AlphaSmart via USB cable (the 3000 has no wireless like the later Dana version), and power on my Android phone.  Back to being among the living!

So how do we maintain that level of comfort with our present technology?  We can, with some certainty, only if we carefully utilize the best present technology and strictly adhere to the so-called "best practices" of security.

Basic Anonymity and Privacy

Even if you feel relatively certain you aren't in need of total anonymity, there are rules being thrown out the window that allow your Internet Service Provider (ISP) to collect your browsing information, and freely share it with anyone or any organization it wishes.  Recent rulings by the FCC indicate that your Internet Service Provider (ISP) may gather this data and do with it what it wishes.

Real World Security

Today's idea of computer security is but a farcical mess.  Everyone is told that they can be secure if they only add on several prophylactic applications designed to protect the flawed operating systems they are so beholden to - mainly because they have been conditioned to believe that these operating systems are their only choice.  These operating systems are continuously vulnerable because of their inherently flawed architecture - and can never be protected simply by adding the defensive sheaths of third-party applications.

The first thing we want to do is adopt a stateless operating system.

Operating System and Hardware

The very first consideration is to choose the operating system that will accommodate the hardware of choice for attaining anonymity.

Our OS dictates the hardware we will choose.  While there are a handful of operating systems that attempt to achieve complete anonymity, the OS we'll be using is called "Tails."

Tails is an exclusively live system that aims to preserve your security, privacy, and anonymity.  It helps you to use the Internet anonymously and circumvent censorship almost anywhere you go and on any computer, but leaves no trace unless you ask it to explicitly.  It is a complete operating system designed to be used from a DVD, USB stick, or SD card (micro preferred) independently of the computer's original operating system.  It is free software and is based on Debian GNU/Linux.  Tails comes with several built-in applications pre-configured with security in mind: Tor web browser, instant messaging client, email client, office suite, image and sound editor, etc.

Tails OS should work on any reasonably recent computer manufactured after 2005.  Here is a specific list of requirements:

Either an internal or external DVD reader or the possibility to boot from a USB stick or SD card (micro SD preferable with or without adapter).  Tails requires an x86 compatible processor: IBM PC compatible and others but not PowerPC nor ARM.  Mac computers are IBM PC compatible since 2006.  2 GB of RAM to work smoothly.  Tails is known to work with less memory, but you might experience strange behaviors or crashes.

Unfortunately, Tails OS documentation does not provide you with a list of hardware that works with the OS.  Rather, it lists issues with hardware it doesn't work properly on.  For our purposes here, I'll just detail my current setup.

I'm currently running Tails OS on an Acer Chromebook 15 CB5-571-C1DZ (15.6-inch full HD IPS, 4 GB RAM, 16 GB SSD).  It is inexpensive and just works.  Plausible deniability is inherent in the system if you have a public identity associated with Google.  Simply login with your Google credentials.

Installing and Booting the Tails OS on the Chromebook

  1. Install Tails OS (tails.boum.org) to a USB drive or a SD card (micro SD preferably).
  2. Fire up the Chromebook.
  3. Use "Esc+Refresh+Power" to enter developer mode.
  4. In recovery mode, press Ctrl+D.  You'll get the message "To turn OS verification OFF, press ENTER."  Your system will reboot and local data will be cleared.  Hit "Enter" and wait.  From now on, you'll get a boot screen that says OS verification is OFF at every startup.  Wait for it.  After a few minutes, your Chromebook will boot into developer mode.
  5. Select debug mode (essential).
  6. To enable USB booting, don't login!  Switch to the dev console by pressing Ctrl+Alt+F2.
    • Type chronos and enter the shell.
    • Type sudo bash to enter root login and enter the default password.
    • Then type: crossystem dev_boot_usb=1 dev_boot_legacy=1
    • Then type exit twice to leave root and dev shell.

  7. Insert Tails OS USB or SD.
  8. Reboot.
  9. On boot, enter Ctrl+L at the ChromeOS splash screen.
  10. Tails OS boots.
  11. Follow the instructions.

Now, read the Tails documentation from start to finish.  Tails doesn't magically secure your privacy and anonymity, so if you use it wrong, you will be compromised.

Conclusion

This is just a basic introduction to securing anonymity and privacy.  There are many more things you will need to do like using burner phones, etc.  It all depends on the level and assurance you need (read paranoia) to maintain your security.  And if you are really paranoid, just unplug - and move to the wild.

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