At 20, he moved to Oakland and eventually began providing tech security for the Rainforest Action Network and Greenpeace. In 2005, a few months after his father died, he traveled alone to Iraq — crossing the border by foot — and set up satellite Internet connections in Kurdistan. In the aftermath of Hurricane Katrina, he drove to New Orleans, using falsified press documents to get past the National Guard, and set up wireless hot spots in one of the city's poorest neighborhoods to enable refugees to register for housing with FEMA.
Upon returning home, he started experimenting with the fare cards used by the Bay Area Rapid Transit system and discovered it was possible to rig a card with an unlimited fare. Instead of taking advantage, he alerted BART officials to their vulnerabilities. But during this conversation, Appelbaum learned that BART permanently stored the information encoded on every transit card — the credit-card number used, where and when they were swiped — on a private database. Appelbaum was outraged. "Keeping that information around is irresponsible," he says. "I'm a taxpayer, and I was given no choice how they store that data. It's not democratically decided — it's a bureaucratic directive."
Given his concerns about privacy, it's easy to see why Appelbaum gravitated toward the Tor Project. He volunteered as a programmer, but it soon became clear that his greatest ability lay in proselytizing: He projects the perfect mix of boosterism and dread. "Jake can do advocacy better than most," says Roger Dingledine, one of Tor's founders. "He says, 'If someone were looking for you, this is what they'd do,' and he shows them. It freaks people out."
The Internet, once hailed as an implacable force of liberalization and democratization, has become the ultimate tool for surveillance and repression. "You can never take information back once it's out there," Appelbaum says, "and it takes very little information to ruin a person's life." The dangers of the Web may remain abstract for most Americans, but for much of the world, visiting restricted websites or saying something controversial in an e-mail can lead to imprisonment, torture or death.
Last year, some 60 governments prevented their citizens from freely accessing the Internet. China is rumored to have a staff of more than 30,000 censors who have deleted hundreds of millions of websites and blocked an eccentric range of terms — not only "Falungong," "oppression" and "Tiananmen," but also "temperature," "warm," "study" and "carrot."
On a bright afternoon in San Francisco, before Wikileaks dominated the headlines, Appelbaum is dressed in his usual hacker uniform: black boots, black socks, black slacks, black thick-rimmed glasses and a T-shirt bearing an archslogan. (Today it's "Fuck politics — I just want to burn shit down.") Though his work requires him to sit at his desk for most of the day, he is rarely stationary. He frequently jumps up and executes a series of brief, acrobatic stretches.He kicks a leg up against the wall, cracks his neck violently, tugs one arm across his chest and, just as abruptly, sits back down again.
He explains that we have to take a cab to pick up his mail. Like being a strict vegan or a Mormon, a life of total anonymity requires great sacrifice. You cannot, for instance, have mail delivered to your home. Nor can you list your name in your building's directory. Appelbaum has all of his mail sent to a private mail drop, where a clerk signs for it. That allows Appelbaum — and the dissidents and hackers he deals with — to use the postal system anonymously. Person One can send a package to Appelbaum, who can repackage it and send it on to Person Two. That way Person One and Person Two never have direct contact — or even learn each other's identities.
Tor works in a similar way. When you use the Internet, your computer makes a connection to the Web server you wish to contact. The server recognizes your computer, notes its IP address and sends back the page you've requested. It's not difficult, however, for a government agency or a malicious hacker to observe this whole transaction: They can monitor the server and see who is contacting it, or they can monitor your computer and see whom you're trying to contact. Tor prevents such online spying by introducing intermediaries between your computer and the system you're trying to reach. Say, for example, that you live in San Francisco and you want to send an e-mail to your friend, a high-level mole in the Iranian Revolutionary Guard. If you e-mail your friend directly, the Guard's network could easily see your computer's IP address, and discover your name and personal information. But if you've installed Tor, your e-mail gets routed to one of 2,000 relays — computers running Tor — scattered across the world. So your message bounces to a relay in Paris, which forwards it to a second relay in Tokyo, which sends it on to a third relay in Amsterdam, where it is finally transmitted to your friend in Tehran. The Iranian Guard can only see that an e-mail has been sent from Amsterdam. Anyone spying on your computer would only see that you sent an e-mail to someone in Paris. There is no direct connection between San Francisco and Tehran. The content of your e-mail is not hidden — for that, you need encryption technology — but your location is secure.
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