Software for the Opposition

Daniel Messer
Cyberpunk Tech & Culture
7 min readNov 9, 2016

I suppose I’ll lose some friends or colleagues with what I’m about to say, and I’m sorry for that. I woke up this morning to news that, for the second time in my life, a Democrat won the popular vote and yet lost the election. Trump claimed the election was rigged, and he was right. The difference is that the election was rigged by our Electoral College system where the popular vote doesn’t mean all that much. Whether or not you believe the Russian hacking conspiracies, the cronyism with the FBI, or that he’s being controlled by aliens… the Electoral College system put him in office. We have a narcissistic, misogynistic, racist, homophobic sociopath as our President Elect. This is a man who’s been outspoken about jailing his competition and who revokes press passes because he doesn’t like what they say about him. He threatens to sue journalists and news outlets.

When someone is that hardcore about their opposition to the very First Amendment of the United States Constitution, you take that man seriously… especially when he’s elected President.

If you want to oppose him, his policies, his office, and his stances on anything, and I mean anything that you care about; I’m telling you right now: You better take some precautionary measures. This is a man who will eventually hold power over the NSA, the CIA, the FBI, the DEA, and all those other wonderful alphabet agencies who no longer make a secret out of spying on their own citizens. I can’t tell you how to protect yourself in meatspace, but I can offer some tips for getting by in cyberspace.

Operating System

The very fundamental heart of your digital devices is the front line for government snooping. Whether or not you trust Windows, macOS, Linux, iOS, or Android; you’re going to have to realize that there are security vulnerabilities in all of them. The experts will tell you to use Linux, but I don’t see that as a realistic thing. People aren’t going to leave their Windows and Mac computers and install something they’ve never seen before. If I have to give you any advice on the operating system front, it’s simply “trust no one.” With the possible exception of Linux, every other operating system is controlled by a corporation and those corporations can be compelled to do things they don’t want to do, or they can happily go along with government requests.

In some ways, you have to accept the idea that you’re already partially compromised simply because you use a computer and that computer probably connects to the Internet. It opens a vector for attack, and you can’t close down all of them without unplugging and walking away. When it came to light that the government, in one form or another, could track you thanks to cellular services (whether the cellular services were complicit or not) — well, to some of us it wasn’t a surprise. For everyone else, I hope that’s a wake up call.

What I can tell you to do is look for a reputable news source for information about your operating systems so you can be informed about what’s going on. Keep everything patched and up to date. If there’s a patch that fixes a security problem, you install that patch immediately.

TAILS

The Amnesic Incognito Live System, or TAILS, is a small operating system that you can carry on a USB drive. It’s designed from the ground up to promote and protect your online anonymity and privacy. It’s a complete operating system on a stick that you can put in your pocket and use to boot many PCs. The PC will boot off the USB and into a Linux environment where there’s software available to allow you to run the net, but remain incognito. Beyond that, the system is encrypted using Linux Unified Key Setup (LUKS), which is a mainstay in digital crypto.

That means that, if you lose your TAILS USB, well that’s a bummer, but you’ll know that the information on it isn’t easily readable by a third party.

Getting down to the heart of it, TAILS is recommended and used by Edward Snowden and promoted by The Freedom of the Press Foundation.

TOR

If you can’t use TAILS, that’s understandable and for many people it’s probably overkill. At the very least, you need to look at TOR. Short for The Onion Router, TOR is a free, open network that protects your online anonymity, your physical location, and your browsing habits. TOR is, quite literally, part of TAILS. From a basic standpoint, TOR works by taking your internet traffic and bouncing it all over the world through a series of virtual connections, rather than connecting you directly to a website or online location. Yes, this will slow down your connection, but what you lose in speed you make up for in privacy.

Thankfully, TOR is easy to use as you can download a ready-to-go, standalone product called the TOR Browser. Just download, install, and when you run it, it’ll fire up a TOR connection, launch a version of Firefox built for privacy, and start routing your web traffic through the TOR network. Keep in mind, only the traffic in that TOR Browser is going out over the TOR network. If you open up Chrome or something, that traffic flows outside of TOR. So keep your private browsing private by keeping it in TOR Browser.

VPN

A virtual private network, or VPN, anonymizes your internet traffic straight from your computer out to the rest of the world. At its basic level, a VPN takes your traffic and routes it through someplace else. Unlike the TOR network, a VPN might only make one or two hops, so your speed won’t suffer so much. You want a paid VPN, because a free VPN is going to do something that compromises your security to make up for the fact that you’re using a free VPN, okay?

Like TOR, a VPN can make you appear to be in another location, even another country. Additionally, a VPN encrypts all the internet traffic coming out of your computer. This prevents things like man-in-the-middle attacks and other people from snooping on your connection. Whenever I’m browsing or working in a coffee shop or on a public network, I use a VPN. You should too.

Personally, I use Private Internet Access, but PC Magazine has a rating of some of the best VPN services out there. Do your research, and buy in.

Two Factor Authentication

Two factor authentication, or TFA, is starting to gain ubiquity in the digital world. To understand TFA all you need to do is realize that TFA normally works through a system of “something you know, and something you have.” Using Gmail as an example, if you set up TFA on your account, you’ll set up a system where you need to know your password, and then enter a verification code from a device. (Usually a smartphone.) In other words, to get into your email, you need to know your password and have your phone. That makes it much harder for someone to waltz into your digital world with a simple stolen password. The Google Authenticator app is free on iOS and Android and, as an added benefit, works with other services using TFA. The methods of setting of TFA vary a bit from service to service, but a quick search will easily take you to the instructions. Most services, from Outlook.com to iCloud, are trying to make it as easy as possible and I expect it to become the norm sooner rather than later.

Private Messaging

Almost everyone using a smartphone sends texts. SMS, or baseline texting, is totally insecure and usually retained by your cellular carrier for some period of time. MMS, or multimedia messaging is just as insecure. You’re going to want a secure messaging system with end-to-end encryption. You have a few choices, and some are better than others. Lots of people seem to like Telegram while others espouse the virtues of Signal. Pick one, or use both. Or you could use iMessage so long as you’re communicating from one Apple device to another. Some cryptopunks will fight over which is better because of open source this or publicly vetted that. At this point, just use something that isn’t SMS to send private or personal messages.

Email

Finally, for now, let’s talk email. Gmail, Outlook, Yahoo, and the rest that you’ve probably heard of? All of them are free, and all of them exist to sell you something. And do you know how they sell you something? They parse the email looking for keywords. So if you and a mate email each other about meeting for a beer later, you’re likely to see an ad for something beer related. Data collected is data stored and while sometimes that data is useful to everyone, including you, you should really consider a private, encrypted email service. When it comes to this, ProtonMail is getting lots of love recently. I just signed up myself and, so far, I like it. There’s a free tier, and then there are paid options. I’m trying the free tier but, if I like it, I’m going to buy it.

The difference between services like Gmail and ProtonMail aren’t just the lack of snooping and sniffing, it’s the fact that with ProtonMail you’re going to be asked for two passwords. One password will log you in, and the next one decrypts your email. It’s like having a key for your office door and then a separate key for your file cabinet, you’d need both to get to the files.

And do yourself a favour, don’t use the same password for both of them. That’s just a bad idea.

There’s going to be more to come. I wish there wasn’t, and I wish there wasn’t a need, but there is. Stay safe out there.

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