Abstract: The subject of this research is the legal norms regulating the usage of digital technologies in oversight activity of the executive branch of government, as well as law enforcement practice of utilization of digital technologies for preventive purposes in oversight activity of the executive branch of government. The object of this research is the social relations establishing in the process of digitalization of the prevention of violations of mandatory requirements. The author examines such aspects as usage of artificial intelligence in prevention of violations of mandatory requirements, as well as analyzes the implementation of “digital control” preventive purposes of oversight activity of the executive branch of government. The main conclusions of the conducted research consists in determination of positive experience from implementation of digital technologies for preventing violations of mandatory requirements, as well as in proposal of the new ways of using digital technologies for improving the effectiveness of implementation of preventive vector of oversight activity. The author also revealed a number of problems that may arise in case of close integration of digital technologies into preventive vector of oversight activity. The novelty consists in the fact that this article is first to explore the question of digitalization of prevention of violations of mandatory requirements, analyze the prospects of usage of digital technologies, as well as outline the “problematic” aspects of the phenomenon under consideration.