This article examines the traditional techniques used to investigate cybercrime and the degree of success of their application on dark web activity. It will also introduce the new strategies which attempt to deanonymise the activities of users. There are substantial technical difficulties in decrypting software and associating evidence with perpetrators. From a social justice perspective, it is the premise of this article that, despite the undeniable social benefits of anonymous web-browsing, the magnitude of crime thriving on the dark web is clearly a significant problem for law enforcement. Since the illicit business that takes place in the internet’s digital shadows are simply a reflection of the activities of society offline, the dark web raises important questions surrounding the way we interpret and investigate cybercrime. Given that activity taking place online is often trans-jurisdictional, there is a pressing need for greater cooperation between countries. However, there is also the more contentious question of what the correct balance is between protecting freedom of expression and the enforcement of law. The main aim of this article is to highlight the inequality of policing between dark web crime and offline crime, and the reasons why exactly the phenomenon has proved such a nemesis for the state.