Alex Winter's Deep Web, which premieres on the Epix channel this Sunday night, tells a tale that's both tragic and alarming. Tragic, because its protagonist, Ross Ulbricht, the "Dread Pirate Roberts" of the now-quashed Silk Road online drug market, destroyed his life in the practice of apparently sincerely held anarcho-libertarian ideals. And alarming, because the way in which the federal government finally nailed him raises serious Fourth Amendment issues that have not yet begun to be resolved.

Winter, whose previous documentary, Downloaded, chronicled the rise and fall of the Napster file-sharing service, begins by mapping out the Deep Web. It's a vast terrain, thousands of times larger than the "visible" Internet, that's filled with un-indexed content such as banking data and corporate and governmental administrative code. Drilling deeper, we come to the Dark Net, a "hidden" area that's accessible only by use of heavily encrypted Tor software. The Dark Net is prime territory for the world's political dissidents, whistle-blowers, investigative journalists—and, of course, criminals.

The Silk Road appeared on the Dark Net in the summer of 2011. It wasn't the first online drug market, but it was the first to trade in Bitcoin crypto-currency, which made transactions nearly impossible to track. The site offered thousands of high-grade drugs: heroin, cocaine, oxycodone, cannabis, DMT, steroids. Delivery was fast and free, and soon nearly a million buyers and sellers were doing business on it. The FBI and DEA took an immediate interest, and after a New York senator, Charles Schumer, demanded that something be done, federal agents began infiltrating the Silk Road as undercover vendors and customers.

In February 2012, one of the Silk Road's various administrators adopted a name: Dread Pirate Roberts. This was a handle borrowed from the 1987 film The Princess Bride, in which it was said to be a hereditary title, passed from one DPR to the next. Andy Greenberg, a senior writer at Wired, managed to establish a connection with the Silk Road's DPR, and began a long, encrypted email interview with him. Greenberg was struck by the site's philosophical underpinnings. Its threads featured much talk of libertarian principles ("We are not beasts of burden to be taxed and controlled"), Austrian Economics and anarcho-capitalism. "At its core," DPR told Greenberg, "Silk Road is a way to get around regulation from the state. The state tries to control every aspect of our lives. Not just drugs."

DPR told Greenberg that it was not he who created the Silk Road: "My predecessor did…I am not the first administrator of Silk Road." He also listed things in which the site did not traffic: stolen goods, counterfeit money or coupons, child pornography, hitman contracts. This didn't seem like an average criminal enterprise. DPR, Greernberg says, "wanted to see a new relationship between individuals and government."

The movie traces the roots of digital libertarianism to the 1990s Cypherpunks—a Bay Area group of mathematicians, hackers and crypto-anarchists dedicated to individual liberty, anonymity and privacy. (In an old interview, one of the group's founders, Eric Hughes, warns that "government wants to access everything.") Today, says ACLU technologist Christopher Soghoian, "There is a community of people…who want to live in a world where government can't read their emails, listen to phone calls, see who they're spending time with." And Cindy Cohn, legal director of the Electronic Frontier Foundation, tells Winter, "An observed life is not a completely free life…A zone of privacy is just a core human value."

In October 2013, the FBI finally shut down the Silk Road Website. And in a public library in San Francisco, they arrested 29-year-old Ross Ulbricht, in very incriminating circumstances. Ulbricht was on his laptop, logged onto the Silk Road "mastermind" account. On his hard drive, investigators discovered thousands of pages of logs detailing his oversight of the Silk Road.

Deep Web is carefully neutral in considering Ulbricht's guilt or innocence. He's an unlikely crime lord—a boyish onetime Eagle Scout with a bachelor's degree in physics and a master's in material science and engineering. In school, he developed a deep interest in Austrian Economics, and particularly the work of Ludwig von Mises. In a 2010 LinkedIn post, he said, "I want to use economic theory as a means to abolish the use of coercion and aggression amongst mankind. Just as slavery has been abolished most everywhere, I believe violence, coercion and all forms of force by one person over another can come to an end."

But is creating an online drug bazaar the best way to test this ideal? The Silk Road claimed to eliminate violence from drug transactions by taking them out of back alleys and making them completely private. (According to an article in Wired, this appears to have worked, to some extent.) And there could be other cultural benefits. Winter talks to Neill Franklin, a former Baltimore policeman who now heads an anti-drug-war group called Law Enforcement Against Prohibition. Franklin points out that the drug trade is a $320-billion industry. "You'll never shut it down," he says—not least because it fattens both corporate interests (private prisons, drug-testing companies) and local police departments (which benefit from over-infusions of outlandishly inappropriate military gear). And so the War on Drugs continues, and the human wreckage mounts.

The government case against Ross Ulbricht is damning, but filled with small, troubling holes—delays in delivery of discovery evidence, prohibition of defense discussion of alternative suspects (there's at least one). There have also been some very strange murder-for-hire charges bandied about. But the most pressing issue is: How did the government manage to gain access to the Silk Road's hidden Icelandic server to gather evidence? Did they simply hack it, without a warrant? As Ulbricht's lawyer, Joshua Dratel, tells Winter: "The government has prosecuted other people for doing essentially what the government did here." And Greenberg says, "American law enforcement hacked a foreign server, I believe, and they didn't have a warrant, and they completely got away with it." This, he says, "could [set] a lasting precedent for how the Fourth Amendment works in the digital age."

Ross Ulbricht is going down (already convicted of seven charges, he'll be sentenced in a New York federal court today), but the forces of government will always be playing catch-up with the cypherpunks. In the movie's eeriest passage, Winter flies to London for a late-night encounter with a group of anarcho-hackers dedicated to creating their own republic of radical anonymity. "The real base of power lies with us," one of them says. "We are the darkness."