Op-Ed: Going Dark—Encryption and the Dark Web

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Examining the “going dark” debate, the dark web and law enforcement’s challenges in investigative measures.

The consistent use of encryption is a necessity on the dark web. In fact, Pretty Good Privacy (PGP) should be used a whole lot more, as emails sent without PGP can be easily intercepted.

The Federal Bureau of Investigation (FBI)’s big problem, according to the organization themselves, is the societal shift to “going dark.” From the outside, this looks like the FBI has waged an apparent war on encryption.

The importance of encryption and the value of anonymity that the dark web can provide can help shape and develop the society we want to live in. But the FBI is not this omnipotent infallible organization: it has political tugs and pulls whether it wishes to publicly acknowledge them or not.

By weakening the legal avenues for lawfully penetrating encryption, legal decryption can match technology; technology which allows decryption of our devices relatively quickly.

“Going Dark”

There is a major buzz around law enforcement and the information security industry in relation to
“going dark.” It’s catchy. It sounds compelling. It makes the ears of the mainstream stand up in attention.

Going dark has been pushed as a major problem for the FBI, and they have been a vocal regarding the issue.

Your TOR usage is being watched

Apple and its iPhones have been outed as a significate problem insofar as law enforcement are concerned. The battle continues, with Apple strengthening its encryption standards.

Not only that, the global zeitgeist in the West has shifted, if ever so slightly, towards an acute awareness that we’re all being watched.

This isn’t science fiction, this isn’t a distant dystopia; this is the reality and opportunity cost for carrying a powerful computer around wherever we go. This is the cost of our thirst.

The solution that we’ve all started gravitating towards is these “safe” services that are “end-to-end encrypted.”

This encryption protocol has been genuinely pitched through marketing as a defining factor. It’s no small feat, to take a consumer-protecting characteristic of technology and spin it into something that a consumer genuinely wants.

Signal and Telegram for example—these are companies that are thriving in the post-Snowden world.

These are the organizations that the FBI sees as the enemy. These are the organizations that are providing the tools for everyday end users to “go dark,” without even thinking twice about it.

End-to-End Encryption

End-to-end encryption is a protocol that has become one major slice of the “going dark” pie. It has worked its way into everyday messaging without making it difficult for users to implement.

This is a key: the ease of implementation. It is too simple for someone with little to no technical knowledge to just download an app like Telegram and start a private chat. This issue of implementation is what has held PGP back as an end-to-end email encryption tool.

Against something like Telegram, PGP is difficult, cumbersome and fiddly. It requires some technical knowledge, and it involves multiple options in setup as well as multiple steps—any of which could go wrong and take someone without a background in technology off the tracks.

Following on with a company like Telegram—it recently stood up for consumer rights against the nation state of Russia. No small task. It proudly advised that it believed in freedom and privacy.

A badge of honor even. Something that the marketing team can run away with on their merry way. This all circles in the mind of an end user.

And it most certainly rattles the investigative teams at the FBI. Their jobs become much harder. With end-to-end encryption, they are unable to wiretap, essentially.

Wiretapping is a legitimate tool when conducting a lawful investigation, though its merits are fading away.

Whatever your views may be about the scope of these wiretapping programs and the secret courts, there are real courts on public record making real decisions to collect evidence in ongoing investigations.

It’s difficult to stop this, without standing in the way of legitimate justice. It’s a fine line. This is where the problems start, and the real grey sky of the issue opens up.

The Dark Web

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The consistent use of encryption is a necessity on the dark web.

It’s like technology as a whole is becoming more and more cynical. Some of us place active microphones in our homes to order washing laundry detergent or ask what the weather is, as if looking through a window is too difficult.

But there is a minority which is steadily growing, on the back of companies cut from the same cloth as the end-to-end messaging service companies that are actively about reducing the digital footprint. And whether users are aware or not, they are reducing their attack surface.

How does the dark web fit into this all? Anonymity is the link. It’s becoming valued in our society. Slowly but surely.

Yes, there is always a sense of apathy among the general population: those that will turn left if the flock turns left, no questions asked.

But there is a demand for rights protection. There are companies satisfying the market’s demand.

There is money to be made in protecting people’s communication and identity. While this goes on, some of these people learn more and more.

They may eventually seek a free place to exchange ideas and information and goods and services.

They may become aware of the dark web and begin interacting. All the while, the FBI and other law enforcement agencies concurrently televise efforts to squash the “party,” general citizens are learning.

Kill one darknet exchange and three others pop up. This isn’t a technological battle—this is a battle on the way we choose to live.

The abilities and freedoms we choose for ourselves. Going dark is becoming a necessary answer to the invasion of privacy. In a sense is that not the hand of the free market truly meeting the needs and wants of the people?

Apple iPhones

Apple’s iPhone changed everything a short while ago. It gave people the ability to walk around while holding a relatively powerful computer.

Certainly today, iPhones have the processing power at least equal to, and possibly more than, many netbooks on the market.

With these devices, law enforcement took advantage of the new information stream that phones provided. Constantly requesting notifications from specific towers—logging location, for example.

The San Bernardino shooting, tragic enough of an event, was used as a line in the sand. The FBI did not seek a technology-driven solution for gaining access to the handset of the attacker; it sought a legal precedent, something that was much more powerful at the time.

We learn this as fact, no longer as speculation, on the back of the Department of Justice’s report stating that the FBI held out and delayed the decryption of the shooter’s handset, in order to pressure Apple to hand over the keys to the car.

This case became political. It was a systematic methodology to put justice to one side, in an effort to set a powerful precedent.

The FBI wanted the ability to decrypt everyone’s handset. Apple protested, publicly defending its defiance. The FBI lost the battle and the world of communication remained “dark.”

A Problem Without an Easy Answer

Isn’t this what investigation and justice is supposed to look like? A field cast in darkness, millions of citizens going about their lawful business, the presumption of innocence on their side. The FBI has the flashlight, instead of the sun.

Isn’t that targeted, singular beam of light shining on one particular user, one spot in the field, isn’t that how investigations should be conducted? Not according to law enforcement. They want the night to end.

They want to see every person in the field bathed in light. And they may have a point. Their jobs are stunted in a world that moves a mile a minute.

With more visibility, it’s possible that we as citizens would be better protected. This is the trade-off. Freedom, autonomy and privacy, or bureaucracy, protection and state power. It’s difficult.

The “going dark” debate is far from over.



Con's education background is law, where he's published on crypto-currency regulation. His opinion editorials range across the relationships between people and technology and the societal challenges it presents. His passion is for information security and the intertwining legal issues
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