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

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.In Little Brother, the series’ first book, Doctorow’s narrator was the idealistic and ultimately naive crypto-rebel Marcus Yallow. 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 of Attack Surface’s release. “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 protestors at the Republican National Convention to Tibetan monks demonstrating against Chinese rule.Little Brother quickly became the book Freitas tried to convince every young technologist to read, to recruit them into a more political use of cryptography and hacking. “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 into Informacam, designed to pull in phone sensor data and embed it in images to prove the authenticity of photos taken by protestors, such as images documenting police violence.In February of 2013, Doctorow published another Little Brother book titled Homeland. 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 Brother might 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 20s, long before Poitras handed him that copy of the second Little Brother book. “A bunch of people who grew up reading Little 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, a longtime 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. 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.