This article examines the history of technological policing in Germany from the 1970s to today. Combining perspectives from intellectual history and legal theory, it explores the ideas and practices of Horst Herold, former President of the German Federal Criminal Police Agency. Herold’s thought was both deeply influenced by cybernetics, a form of techno-utopian thought developed during World War II as well as the basis on which technological policing was first put to the test in Germany. The article illustrates Herold’s hopes for a cybernetic transformation of police, law, and society. It locates Herold’s cybernetic legal theory within a broader context of shifting legal paradigms of German public law towards the so-called preventive state in the 1970s and 80s. Crucially, an anti-legal affect is revealed to lie at the center of Herold’s ideas. His concept of cybernetics ultimately serves to supplant the rule of law. In the concluding part, the article assesses Herold’s legacy and attempts to both critique it and point towards a productive way forward by invoking modern, second-order order cybernetics. The article argues—perhaps counterintuitively—that Herold’s ultimate failure was not adapting cybernetics but rather not staying with it all the way, supplanting its weaknesses, and drawing on its strengths.