The Dark Web, and the technology which underpins it, is fundamentally changing how crime is conducted. It is an enabler of cross-border, truly international crime where each of the major actors, evidence, and the proceeds of crime can all be in different jurisdictions. The technologies utilised mask the identity of individuals and the nature of the crimes committed. It is these complexities, and law’s inability to deal with them, which this paper will focus on. It critically analyses six intersecting and overlapping themes in order to highlight the technological challenges posed by the Dark Web to the criminal law. The paper argues that the current approaches, regulatory structures, legislation and investigative methods are all unfit for purpose. There is little to suggest the law is any closer to restricting Dark Web crime, particularly given a substantial amount of the challenges posed are unsolved traditional issues, in a new form.