The dark web’s inherent hostility to observation makes it the perfect place for whistleblowers, freethinkers… and criminals. This design, build with anonymity and fully private operations in mind, also makes it almost impossible to use. Is there a future where the dark web is both easy to use and still maintains the core functionality necessary to protect its users? Does making the dark web easier to use inherently open it up to unchecked monitoring by private companies and law enforcement? Will legal users of the dark web be swept up in efforts to crack down on illegal activity on the dark web? And if we do see a growth in ease of use tools, is someone finally going to make a Clippy for the dark web? This session will cover the underlying structure of the dark web and the of “ease of use” tools developed for dark web users over time, specifically the tools that facilitate ecommerce for buyers in a diversified criminal market. This talk will also address the inherent tension between the dark web as a bastion of privacy and anti-authoritarian sentiment and the dark web as a usable, functional repository of institutional knowledge. If you’ve heard of the dark web before but your first thought is “I think I remember Silk Road was a thing,” this talk may be for you.