The issue of countering illegal cash withdrawal remains urgent due to the steady reproduction of such practices under any institutional changes. Such operations reduce tax revenues, distort the competitive environment, substitute reliable reporting and make it difficult to establish predicate crimes. At various historical stages, they have been fueled by the limitations of legal payment channels, regulatory gaps in transition periods, high costs of complying with legal requirements, and the specifics of the payment infrastructure. The digitalization of finance, remote identification, and the emergence of new intermediaries have reinforced these trends, with currency restrictions and the restructuring of cross-border payments added in 2022–2025. The focus of attention of law enforcement agencies remains the distinction between bona fide economic activity and criminal activity, competition of norms, as well as the correct assessment of commodity- free transactions and fictitious services. The retrospective approach makes it possible to link institutional changes with the evolution of the schemes used, to determine the reasonable limits of criminal law intervention and to trace the formation of the socio-legal conditionality of countering behavior that has long demonstrated not just illegal, but truly socially dangerous.