His Writing Radicalized Young Hackers. Now He Wants to Redeem Them

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https://www.wired.com/story/his-writing-radicalized-young-hackers-now-he-wants-to-redeem-them/

His Writing Radicalized Young Hackers. Now He Wants to Redeem Them

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Cory Doctorow’sLittle Brotherseries has been a young-adult sci-fi bible for teen hacktivists. But with the latest and darkest book in the trilogy, it’s all grown up.

SET THE FIRSTand last books in Cory Doctorow’s epic, three-bookLittle Brothercypherpunk saga side by side, and they read a bit like a creative writing master class on telling two starkly opposite stories from the same prompt. The common premise: Islamist terrorists bomb the Bay Bridge. Thousands die. The Department of Homeland responds by turning San Francisco into a fascist, total-surveillance police state. The protagonist, a digitally gifted, troublemaking teen, must decide how to respond.

In the firstLittle Brotherinstallment, which Doctorow published in 2008, the answer seemed righteously inevitable: The hero uses his hacker skills to fight back. Specifically, he and his plucky hacker friends figure out how to jailbreak their Xboxes and channel the video game consoles’ encrypted comms over the Tor network to create Xnet, a cheap, anonymous, surveillance-proof system for organizing protest and foiling the panopticon cops by injecting false data into their totalitarian schemes.

In Doctorow’s third work in the series,publishing this week and titled Attack Surface, the protagonist takes an altogether different path. And while that path threads through the same alternate-world timeline of events, it’s tinted with all the shades of gray that the world has accumulated in the dozen long years since the series’ first, wide-eyed story.

This time the hero—or antihero, more like—instead chooses to go work for the DHS. After all, she’s angry, itching to use her prowess in digital exploitation, and someone needs to help hunt these terrorists who actually knows what she’s doing. To get the job, she breaks into her friends’ Xnet system—it was riddled with hackable bugs, of course—and uses information cascade modeling to identify all of the resistance’s leaders, then serves up the map to the authorities. Not long after, she swaps her DHS job for a contract position in Iraq, where she uses those same tricks to identify insurgent leaders, hack their devices, find them, and target them for killing.

The money is very good, and it keeps getting better. She’s transferred to Mexico City, switches contractors, and becomes accustomed to flying first-class, room service in Japanese-themed hotels, and aged scotch on the corporate account. Eventually she finds her employer is offering her exploitation skills to a kleptocratic Eastern European government that’s using them to suppress a “color revolution”-style movement. To assuage her guilt, she starts helping the dissidents, too, building surveillance systems by day and advising idealistic young rebels on how to defeat them by night—even while knowing that they’re almost certainly doomed, that the technological terrain has put them at an impossible disadvantage.

InLittle Brother,the series’ first book, Doctorow’s narrator was the idealistic and ultimately naive crypto-rebel Marcus Yallow. InAttack Surface, the latest, it’s the realist, cynical, ethically compromised spy, Masha Maximow. But Doctorow doesn’t want the reader to choose between the two. He wants you to see yourself in both Marcus and Masha, equally, to live out his morality tale from both perspectives. And he argues that second perspective may be far more relatable: His latest book is designed not for the fresh-faced Marcuses who are still ethically unblemished, but for the far larger population of Mashas who have already made moral compromises in their tech careers—who already work at a privacy-invasive social media giant, an adtech firm, a surveillance contractor, or an intelligence agency.

“I want to reach people who are maybe belated Robert Oppenheimers, who are thinking about whether or not it's a good idea to be running this Manhattan Project to manipulate people or spy on people or control people,” Doctorow told WIRED in an interview last week ahead ofAttack Surface’s release. “If you found yourself in tech because you were excited by how much self-determination and power and pleasure you got from mastering technology, and then found your entire professional life devoted to ensuring that no one else ever felt that, this is the time for your moral reckoning.”

Doctorow’s goal isn’t to shame those readers, nor to absolve them. His message for all of those ethically compromised Mashas, he says, is that it’s not too late. “Now is the time to figure out which side of the struggle you're on,” he says. “The side of computers controlling us, or the side of computers giving us control.”

For the last 12 years, Doctorow'sLittle Brotherseries has inspired and influenced digital subversives from Aaron Swartz to Laura Poitras to Edward Snowden.PHOTOGRAPH: JUCO

THE FIRST PERSONto tell me aboutLittle Brotherwas John Gilmore, cofounder of the Electronic Frontier Foundation and of theoriginal Cypherpunks, the 1990s techno-libertarian group that coined the term. As we sat in a coffee shop in San Francisco’s Mission District on a rainy day in 2011, Gilmore talked me through the whole cypherpunk canon: Tim May’sCyphernomicon, Eric Hughes’ “Cypherpunks’ Manifesto,” and the legendary Cypherpunks Mailing List, which Gilmore had once hosted on his own server and whose archives he copied onto a USB drive for me on the spot. And by the way, had I heard about a very interesting young-adult fiction book about teens using crypto tools to take on the DHS?

By then, in fact,Little Brotherwas already a best seller and was quickly becoming required reading for a certain class of young, digital dissidents. When Nathan Freitas, today the director of the smartphone-focused privacy nonprofit Guardian Project, downloaded the ebook in 2008, he found that it captured his experience unlike anything he’d ever read before. “It was the world I had lived in since 9/11,” says Freitas, who at the time had left a job as a developer for mobile device firm Palm to become a pro bono security consultant, working on behalf of every underdog from protesters at the Republican National Convention to Tibetan monks demonstrating against Chinese rule.

Little Brotherquickly became the book Freitas tried to convince every young technologist to read, to recruit them into a more political use of cryptography and hacking. Over the following years he watched it grow into a kind of bible for the digital protest movement, a piece of science fiction that felt far more immediate and urgent than sci-fi’s hacker classics. “It was a call to action for people who then would reference it in the way that people used to referenceSnow CrashorNeuromancer,” Freitas says. “It was a kind of touchstone for this idea that ‘now it's serious, now the internet is connected to our lives and war and oppression and surveillance.’”

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In 2009, Freitas putLittle Brotheron the reading list for a class he taught at New York University's Interactive Telecommunications Program. One of the graduate students in that NYU class was Harlo Holmes, who today serves as director of digital security at the Freedom of the Press Foundation,teaching activists and journalists how to combat surveillance.

Holmes says that reading Doctorow’s book changed her life. “There was nothing more fundamental to my particular origin story than the semester I spent in that class and readingLittle Brother,” Holmes says. “It informed my thoughts around how privacy should work, the interplay between movement activists, technology, and the law, and what you should look out for when inviting technologies into your life to do that movement building.” Holmes’ final project for Freitas’ class was a smartphone camera tool she called “A Bigger Brother,” which has since evolved intoInformacam, designed to pull in phone sensor data and embed it in images to prove the authenticity of photos taken by protesters, such as images documenting police violence.

In February 2013, Doctorow published anotherLittle Brotherbook titledHomeland. This sequel told the story of how Doctorow’s hero, Marcus Yallow, is given a USB drive full of scandalous, classified secrets from spy agencies—torture, drone strikes, mass surveillance—and has to decide how to make it all public without inflicting collateral damage on innocent lives, including his own.

The book featured an afterword from Aaron Swartz, the young hacktivist who had been criminally prosecuted for downloading a collection of academic papers from the paywalled repository JSTOR in the hopes of making them freely available. Just two months beforeHomeland’s release, facing years in prison,Swartz had committed suicide. His posthumous words resonated inHomeland’s pages: “The system is changing,” Swartz wrote. “Thanks to the Internet, everyday people can learn about and organize around an issue even if the system is determined to ignore it. Now, maybe we won’t win every time—this is real life, after all—but we finally have a chance.”

A month later, documentary filmmaker and journalist Laura Poitras was readingHomelandwhile exchanging PGP keys and encrypted emails about bombshell NSA documents with a source she knew only as “Citizenfour.” Poitraswrote in her journalthat the book “feels likes a mirror of the exact fucking reality I’m living in. National security leaks, detention, threat of death, key passing.”

A few months later, Poitras traveled to Hong Kong withGuardianjournalists Glenn Greenwald and Ewan MacAskill to meet Citizenfour, whose real name was Edward Snowden. She gave Snowden a copy ofHomeland. After the whistleblower and journalists had collaborated to publish the biggest leak of NSA secrets in history, Snowden took the book with him on his journey into exile in Russia. In her subsequent documentary about Snowden,Citizenfour, Doctorow’s book appears on the bedside table of his hotel room, next to a tangle of cables and piled laptops.

“That moment inCitizenfourwhere Snowden grabs a copy ofHomelandand sticks it in his go bag, that’s kind of the apotheosis of it right there,” Doctorow says. “That was the moment when I thought, in some tiny way, I have been part of the moral instruction of some part of the current generation of technologists. The idea that now, whenever someone sits down to make a choice—do I take power away from users or do I give it to them?—Little Brothermight be weighing on their conscience, that is an awesome responsibility and a source of incredible pride.”

Snowden himself says he's been reading Doctorow since his early twenties, long before Poitras handed him that copy of the secondLittle Brotherbook. "He is to me a radical idealist, because no matter how bad things get, his mind goes to the stories of cooperation and creation-sharing," Snowden wrote in a text message to WIRED. "When the traditional structures of oppression are up to no good, as was the case inLittle Brother, Cory doesn't reflexively indoctrinate young readers with platitudes on the inevitability of corruption. He helps them reimagine the limits of their own power."

“Cory doesn't reflexively indoctrinate young readers with platitudes on the inevitability of corruption,” Edwards Snowden says. "He helps them reimagine the limits of their own power."PHOTOGRAPH: JUCO

DESPITE THE DARK-AS-TOMORROW’S-HEADLINESthemes at their core,Little BrotherandHomelandwere young-adult novels, a two-part teen radical’s primer.Attack Surface, by contrast, is for actual adults, Doctorow says. Not because it has more adult language, violence, or sex—Doctorow cut the only sex scene in the book from the final draft—but because it deals with the very adult problem of having lived an ethically imperfect life.

“The thing adults do is confront their moral legacy. They look back on what they've done and they think about their regrets,” Doctorow says. “The ongoing process of being an adult is having been corralled into compromises and then making sense of those compromises for yourself.”

Doctorow says the book is meant to stand alone for new readers—even non-techy, civilian observers on the sidelines of the crypto wars—but that it’s also meant to speak to the core, cypherpunk audience of the first twoLittle Brotherbooks. And that includes the ones who didn’t turn out to be the heroes of their own story. “A bunch of people who grew up readingLittle Brother, imagining that they would become revolutionaries, woke up one day and realized that they're not revolutionaries, that in fact they're helping to make things worse, that they're part of a system that harms people,” says Eva Galperin, alongtime digital activist and head of the Electronic Frontier Foundation’s Threat Lab. Galperin serves in part as the inspiration for Masha’s character—both hackers, fictional and nonfictional, were born in the Soviet Union but grew up in San Francisco with immigrant parents.

But Galperin sees Masha also in her idealistic friends who went to work for Facebook or Palantir or government agencies, vowing to change them from the inside but finding themselves changed instead. “This is a book for the people who realize that they've grown up and made a lot of compromises,” Galperin says, “and about how you turn back from that.”

Attack Surface at some points reads almost like an admission of regret from Doctorow himself. When Masha describes how easily she exploited and rolled up Marcus Yallow’s Xnet for the DHS or the limits of encryption in an era when spy agencies and their contractors have hoards of zero-day vulnerabilities they can use to hack their targets, the book seems to be walking back a degree of technological solutionism that has long since gone out of style. At times it seems to even flirt with defeatism, conceding that all the techniques that worked to stop mass surveillance in Little Brother become useless the instant a sophisticated adversary has identified you as a subject for targeted surveillance.

At one point, Doctorow writes in Masha’s voice about the hero of his earlier works in a passage that might also be read as Doctorow berating his past self:

“What I truly hated about Marcus Yallow, above all else, was this: He gave people hope when no hope was called for. He told them they could master their computers and their networks, communicate in private and in secret, form networks of mutual aid and use them to bring down the powerful and unjust. But I’ve been on the other side of the data center, I’ve seen how hard it is to cover your tracks, to be perfect in your opsec, to know who and what to trust, to write code that is flawless.”

But Doctorow says that the intention ofAttack Surfacewasn’t to swing in the other direction on the spectrum between “nerd triumphalism” and “nerd despair,” as he puts it. Instead, it’s to find a more nuanced middle ground, one that acknowledges that technology can win some battles, but that others must be won with human willpower and political struggle, sometimes with the aim of controlling technology’s most dangerous applications.

The title ofAttack Surfacecomes from thecybersecurity term for a target system’s exposure to exploitation: The more attack surfaces—external connections and inputs—the more vulnerable the system is to hacking. But Doctorow says he chose the title because he defines “attack surface” as the volatile edge where two systems meet. Those systems might be a hackable device and the internet, or technology and the law, or even technology and human beings, with each having the power to potentially exploit the other.

Those edges add up to a far more complex and unpredictable picture than the one Doctorow sketched inLittle Brother. The world ofAttack Surfaceis one where technology isn’t necessarily a force for good or evil, but where it has to be bent to the right cause by human ethics. “Technology is a tool that gives us space to make political change. Politics are a tool we use to open the space for making better technology,” one wise character summarizes near the end ofAttack Surface, lecturing both Marcus and Masha. “It’s like parallel parking: You go as far as you can in one direction, then back up and go as far as you can in the other.”

Across its three-book arc, theLittle Brothernow achieves something similar: After driving his car to the extremes of digital idealism, Doctorow has backed it up to the other extreme of digital pessimism. And in doing so, he’s carved out a space for himself to fit a far messier truth between the two.