Surveillance Valley

by Yasha Levine

  Internet Freedom required a new set of “soft-power” weapons: digital crowbars that could be used to wrench holes in a country’s telecommunications infrastructure. In the early 2000s, the US government began funding projects that would allow people inside China to tunnel through their country’s government firewall.52 The BBG’s Internet Anti-Censorship Division led the pack, sinking millions into all sorts of early “censorship circumvention” technologies. It backed SafeWeb, an Internet proxy funded by the CIA’s venture capital firm In-Q-Tel. It also funded several small outfits run by practitioners of Falun Gong, a controversial Chinese anticommunist cult banned in China whose leader believes that humans are being corrupted by aliens from other dimensions and that people of mixed blood are subhumans and unfit for salvation.53

  The Chinese government saw these anticensorship tools as weapons in an upgraded version of an old war. “The Internet has become a new battlefield between China and the U.S.” declared a 2010 editorial of the Xinhua News Agency, China’s official press agency. “The U.S. State Department is collaborating with Google, Twitter and other IT giants to jointly launch software that ‘will enable everyone to use the Internet freely,’ using a kind of U.S. government provided anti-blocking software, in an attempt to spread ideology and values in line with the United States’ demands.”54

  China saw Internet Freedom as a threat, an illegitimate attempt to undermine the country’s sovereignty through “network warfare,” and began building a sophisticated system of Internet censorship and control, which grew into the infamous Great Firewall of China. Iran soon followed in China’s footsteps.

  It was the start of a censorship arms race. But there was a problem: the early anticensorship tools backed by the BBG didn’t work very well. They had few users and were easily blocked. If Internet Freedom was going to triumph, America needed bigger and stronger weapons. Luckily, the US Navy had just developed a powerful anonymity technology to hide its spies, a technology that could easily be adapted to America’s Internet Freedom war.

  Russia Deployment Plan

  When Tor joined the Broadcasting Board of Governors in early 2006, Roger Dingledine was aware of America’s escalating Internet Freedom conflict and accepted Tor’s role as a weapon in this fight. China and Iran were throwing up ever more sophisticated censorship techniques to block US programming, and Dingledine talked up Tor’s ability to meet this challenge. “We already have tens of thousands of users in Iran and China and similar countries, but once we get more popular, we’re going to need to be prepared to start the arms race,” he wrote to the BBG in 2006, laying out a plan to progressively add features to the Tor network that would make it harder and harder to block.55

  The Tor Project was the BBG’s most sophisticated Internet Freedom weapon, and the agency pushed Dingledine to reach out to foreign political activists and get them to use the tool. But as Dingledine quickly discovered, his organization’s ties to the US government aroused suspicion and hampered his ability to attract users.

  One of those lessons came in 2008. Early that year, the BBG instructed Dingledine to carry out what he dubbed the “Russian Deployment Plan,” which involved adding a Russian language option to Tor’s interface and working to train Russian activists in how to properly use the service.56

  In February 2008, weeks before Russia’s presidential elections, Dingledine sent an email request to a Russian privacy activist named Vlad. “One of our funders… [the Broadcasting Board of Governors] wants us to start reaching out to real users who might need these tools at some point,” Dingledine explained. “So we settled on Russia, which is increasingly on their radar as a country that may have a serious censorship problem in the next few years.… So: please don’t advertise this anywhere yet. But if you’d like to be involved in some way, or you have advice, please do let me know.”57

  Vlad was glad to hear from Dingledine. He knew about Tor and was a fan of the technology, but he had doubts about the plan. He explained that censorship was not currently an issue in Russia. “The main problem in Russia at this time is not a government censorship (in the sense of the Great Firewall of China or some Arab states), but a self-censorship of many websites, especially of regional organizations. Unfortunately, this is not what Tor can entirely solve by itself,” he replied. In other words: Why fix a problem that did not exist?

  But a bigger question hung over Dingledine’s request, one concerning Tor’s ties to the US government. Vlad explained that he and others in Russia’s privacy community were concerned about what he described as Tor’s “dependence on ‘Uncle Sam’s’ money” and that “some sponsors of the Tor Project are associated with the US State Department.” He continued: “I understand this is an ambiguous and quite vague question, but do such sponsorship brings up any unusual issues to the Tor Project and Tor development process?”

  Given the deteriorating political relations between Russia and the United States, the subtext of the question was obvious: How close was Tor to the US government? And, in this strained geopolitical climate, will these ties cause problems for Russian activists like him back home? These were honest questions, and relevant ones. The emails I obtained through the Freedom of Information Act do not show whether Dingledine ever replied. How could he? What would he say?

  The Tor Project had positioned itself as an “independent nonprofit,” but when Dingledine reached out to Vlad in early 2008, it was operating as a de facto arm of the US government.

  The correspondence left little room for doubt. The Tor Project was not a radical indie organization fighting The Man. For all intents and purposes, it was The Man. Or, at least, The Man’s right hand. Intermixed with updates on new hires, status reports, chatty suggestions for hikes and vacation spots, and the usual office banter, internal correspondence reveals Tor’s close collaboration with the BBG and multiple other wings of the US government, in particular those that dealt with foreign policy and soft-power projection. Messages describe meetings, trainings, and conferences with the NSA, CIA, FBI, and State Department.58 There are strategy sessions and discussions about the need to influence news coverage and control bad press.59 The correspondence also shows Tor employees taking orders from their handlers in the federal government, including plans to deploy their anonymity tool in countries deemed hostile to US interests: China, Iran, Vietnam, and, of course, Russia. Despite Tor’s public insistence it would never put in any backdoors that gave the US government secret privileged access to Tor’s network, the correspondence shows that in at least one instance in 2007, Tor revealed a security vulnerability to its federal backer before alerting the public, potentially giving the government an opportunity to exploit the weakness to unmask Tor users before it was fixed.60

  The funding record tells the story even more precisely. Aside from Google paying a handful of college students to work at Tor via the company’s Summer of Code program, Tor was subsisting almost exclusively on government contracts. By 2008, that included contracts with DARPA, the navy, the BBG, and the State Department as well as Stanford Research Institute’s Cyber-Threat Analytics program.61 Run by the US Army, this initiative had come out of the NSA’s Advanced Research and Development Activity division—a “sort of national laboratory for eavesdropping and other spycraft” is how James Bamford describes it in The Shadow Factory.62 And a few months after reaching out to Vlad, Dingledine was in the middle of closing another $600,000 contract with the State Department,63 this time from its Democracy, Human Rights, and Labor division, which had been created during President Bill Clinton’s first term and which was tasked with doling out grants for “democracy assistance.”64

  What would someone like Vlad think of all this? Obviously, nothing good. And that was an issue.

  The Tor Project needed users to trust its technology and show enthusiasm. Credibility was key. But Dingledine’s outreach to Russian privacy activists was a rude reminder that Tor couldn’t shake its government affiliation and all the negative connotations that came with it. It was a problem tha
t Dingledine had guessed would haunt Tor when he accepted BBG’s first contract back in 2006.

  Clearly, Tor needed to do something to change public perception, something that could help distance Tor from its government sponsors once and for all. As luck would have it, Dingledine found the perfect man for the job: a young, ambitious Tor developer who could help rebrand the Tor Project as a group of rebels that made Uncle Sam tremble in his jackboots.

  A Hero Is Born

  Jacob Appelbaum was born in 1983 on April Fools’ Day. He grew up in Santa Rosa, a city just north of San Francisco, in a bohemian family. He liked to talk up his rough upbringing: a schizophrenic mother, a musician-turned-junkie dad, and a domestic situation that got so bad he had to fish used needles out of the couch as a kid. But he was also a smart middle-class Jewish kid with a knack for programming and hacking. He attended Santa Rosa Junior College and took classes in computer science.65 He dressed in goth black and dabbled in steampunk photography, taking retro-futuristic pictures of young women decked out in Victorian-era dresses in front of steam engines and locomotives. Politically, he identified as a libertarian.

  Like most young libertarians, he was enchanted by Ayn Rand’s The Fountainhead, which he described as one of his favorite books. “I took up this book while I was traveling around Europe last year. Most of my super left wing friends really dislike Ayn Rand for some reason or another. I cannot even begin to fathom why, but hey, to each their own,” he wrote in his blog diary. “While reading The Fountainhead I felt like I was reading a story about people that I knew in my everyday life. The characters were simple. The story was simple. What I found compelling was the moral behind the story. I suppose it may be summed up in one line… Those that seek to gather you together for selfless actions, wish to enslave you for their own gain.”66

  He moved to San Francisco and worked low-level computer jobs with an emphasis in network management, but he chafed at regular tech jobs and pined for something meaningful.67 He took time off to volunteer in New Orleans after Hurricane Katrina and somehow wound up in Iraq hanging out with a military contractor buddy who was installing satellite service in the war-torn country. He returned to the Bay Area more determined than ever to live an exciting life. “Life is too short to waste it on jobs that I do not enjoy,” he said in a 2005 interview.68 One day he’d join a porn start-up company, dress in black, dye his hair red, and pose with a power tool dildo for Wired magazine.69 The next day he’d travel halfway around the world to use his skills for the greater good. “I’m a freelance hacker. I work helping groups that I feel really need my help. They come to me and ask me for my services,” he said. “More often than not, I’m simply setting up their networks and systems around the world. It depends on how I feel about the work they’re doing. It has to be both an interesting job and for an interesting result.”

  Appelbaum also began to develop a bad reputation in the Bay Area hacker scene for his aggressive, unwanted sexual advances. San Francisco journalist Violet Blue recounted how he spent months trying to coerce and bully women into having sex with him, attempted to forcefully isolate his victims in rooms or stairwells at parties, and resorted to public shaming if his advances were rebuffed.70 This pattern of behavior would trigger his downfall almost a decade later. But for now, his star was ascendant. And in 2008, Appelbaum finally got his dream job—a position that could expand with his giant ego and ambition.

  In April of that year, Dingledine hired him as a full-time Tor contractor.71 He had a starting salary of $96,000 plus benefits and was put to work making Tor more user-friendly. He was a good coder, but he didn’t stay focused on the technical side for long. As Dingledine discovered, Appelbaum proved better and much more useful at something else: branding and public relations.

  Tor employees were computer engineers, mathematicians, and encryption junkies. Most of them were introverts, and socially awkward. Even worse: some, like Roger Dingledine, had spent time at US intelligence agencies and proudly displayed this fact on their online CVs—a not-so-subtle sign of a lack of radicalness.72 Appelbaum added a different element to the organization. He had flair, a taste for drama and hyperbole. He was full of tall tales and vanity, and he had a burning desire for the spotlight.

  Within months of getting the job, he assumed the role of official Tor Project spokesman and began promoting Tor as a powerful weapon against government oppression.

  While Dingledine focused on running the business, Jacob Appelbaum jet-setted to exotic locations around the world to evangelize and spread the word. He’d hit ten countries in a month and not bat an eye: Argentina, India, Poland, South Korea, Belgium, Switzerland, Canada, Tunisia, Brazil, and even Google’s campus in Mountain View, California.73 He gave talks at technology conferences and hacker events, pow-wowed with Silicon Valley executives, visited Hong Kong, trained foreign political activists in the Middle East, and showed former sex workers in Southeast Asia how to protect themselves online. He also met with Swedish law enforcement agencies, but that was done out of the public eye.74

  Over the next several years, Dingledine’s reports back to the BBG were filled with descriptions of Appelbaum’s successful outreach. “Lots of Tor advocacy,” wrote Dingledine. “Another box of Tor stickers applied to many many laptops. Lots of people were interested in Tor and many many people installed Tor on both laptops and servers. This advocacy resulted in at least two new high bandwidth nodes that he helped the administrators configure.”75 Internal documents show that the proposed budget for Dingledine and Appelbaum’s global publicity program was $20,000 a year, which included a public relations strategy.76 “Crafting a message that the media can understand is a critical piece of this,” Dingledine explained in a 2008 proposal. “This isn’t so much about getting good press about Tor as it is about preparing journalists so if they see bad press and consider spreading it further, they’ll stop and think.…”77

  Appelbaum was energetic and did his best to promote Tor among privacy activists, cryptographers, and, most important of all, the radical cypherpunk movement that dreamed of using encryption to take on the power of governments and liberate the world from centralized control. In 2010, he snagged the support of Julian Assange, a silver-haired hacker who wanted to free the world of secrets.

  Tor Gets Radical

  Jacob Appelbaum and Julian Assange had met in Berlin sometime in 2005, just as the mysterious Australian hacker was getting ready to set WikiLeaks in motion. Assange’s idea for WikiLeaks was simple: government tyranny can only survive in an ecosystem of secrecy. Take away the ability of the powerful to keep secrets, and the whole facade will come crashing down around them. “We are going to fuck them all,” wrote Assange giddily on a secret listserv, after announcing his goal of raising $5 million for the WikiLeaks effort. “We’re going to crack the world open and let it flower into something new. If fleecing the CIA will assist us, then fleece we will.”78

  Appelbaum watched as Assange slowly erected WikiLeaks from nothing, building up a dedicated following by trawling hacker conferences for would-be leakers. The two became good friends, and Appelbaum would later brag to journalist Andy Greenberg that they were so close, they’d fuck chicks together. One New Year’s morning the two woke up in an apartment in Berlin in one bed with two women. “That was how we rolled in 2010,” he said.

  Soon after that supposedly wild night, Appelbaum decided to attach himself to the WikiLeaks cause. He spent a few weeks with Assange and the original WikiLeaks crew in Iceland as they prepared their first major release and helped secure the site’s anonymous submissions system using Tor’s hidden service feature, which hid the physical location of WikiLeaks servers and in theory made them much less susceptible to surveillance and attack. From then on, the WikiLeaks site proudly advertised Tor: “secure, anonymous, distributed network for maximum security.”

  Appelbaum’s timing couldn’t have been better. Late that summer WikiLeaks caused an international sensation by publishing a huge cache of classified government documen
ts stolen and leaked by Chelsea (née Bradley) Manning, a young US Army private who was stationed in Iraq. First came the war logs from Afghanistan, showing how the United States had systematically underreported civilian casualties and operated an elite assassination unit. Next came the Iraq War logs, providing irrefutable evidence that America had armed and trained death squads in a brutal counterinsurgency campaign against Iraq’s Sunni minority, which helped fuel the Shia-Sunni sectarian war that led to hundreds of thousands of deaths and ethnic cleansing in parts of Baghdad.79 Then came the US diplomatic cables, offering an unprecedented window into the inner workings of American diplomacy: regime change, backroom deals with dictators, corruption of foreign leaders brushed under the table in the name of stability.80

  Assange was suddenly one of the most famous people in the world—a fearless radical taking on the awesome power of the United States. Appelbaum did his best to be Assange’s right-hand man. He served as the organization’s official American representative and bailed the founder of WikiLeaks out of tough spots when the heat from US authorities got too hot.81 Appelbaum became so intertwined with WikiLeaks that apparently some staffers talked about him leading the organization if something were to happen to Assange.82 But Assange kept firm control of WikiLeaks, even after he was forced to go into hiding at the Ecuadorian embassy in London to escape extradition back to Sweden to face an investigation of rape allegations.

  It’s not clear whether Assange knew that Appelbaum’s salary was being paid by the same government he was trying to destroy. What is clear is that Assange gave Appelbaum and Tor wide credit for helping WikiLeaks. “Jake has been a tireless promoter behind the scenes of our cause,” he told a reporter. “Tor’s importance to WikiLeaks cannot be understated.”83