The federal prosecution of Ross Ulbricht, the alleged deep-web black marketeer known as Dread Pirate Roberts of The Silk Road, may have some major flaws when it comes to how the FBI built its case against Ulbricht, according to a new documentary. Even Ulbricht's mom, Lyn Ulbricht, thinks so — and she, by the way, sounds like a pretty badass privacy activist and liberal intellectual in her first on-camera appearance. "We're at a crossroads here," she says, "deciding what kind of internet we want, and what kind of freedoms we want in general."

The documentary, called Deep Web, is crowdfunded and directed by Alex Winter, who, as Wired notes, previously made the film Downloaded about the rise and fall of Napster — so, obviously, concerns about the legalities of the web are his bread and butter. Winters says that people who dismiss The Silk Road as "an exceptional case, involving drugs and dark corners of the internet" are missing some of the key issues. Namely the government's ability to find the Silk Road's servers suggests that they did so without a proper warrant, and a judge has already thrown this argument out on a technicality. It seems likely that the FBI ultimately located the servers in Iceland through illegal hacking, and not, as they claim, because of a configuration flaw in the site's CAPTCHA software. Privacy researcher Runa Sandvik previously told Wired, "The way [the FBI] describe how they found the real IP address doesn't make sense to anyone who knows a lot about Tor and how web application security works."

So it now remains up to Ulbricht's defense attorneys to get a jury to listen to the complicated technological argument behind this, if they're even allowed to use this argument.

Ulbricht's trial is set to begin Tuesday, January 13, and many libertarian and geeky eyes will be watching. "If the prosecution gets away with this warrantless seizure of Americans' data, as well as a lot of foreigners' [data], it could set a lasting precedent for how the Fourth Amendment works in the digital age," says Wired writer Andy Greenberg.

Deep Web will air on Epix later this year.

All previous coverage of the Silk Road case on SFist.