The paper examines how the notion of compliance has evolved into a pervasive and multifaceted mechanism within contemporary economic regulation. Its broad diffusion, however, raises questions when compliance paradigms migrate across distinct legal domains. The analysis explores this issue through the Italian legal landscape, where criminological overlaps between organised crime and corporate criminal deviance have fostered a hybridisation of enforcement strategies and normative models. This dynamic is particularly evident in the preventive measures introduced by the Anti-Mafia Code – judicial administration and judicial control – which target lawful corporations whose organisational shortcomings facilitate criminal conduct. These measures, while demonstrating notable strengths, also reveal important criticalities. They are grounded in a compliance-based rationale inspired by the corporate criminal liability regime under Legislative Decree No 231/2001, and are intended to reorganise the legal entity so as to prevent future episodes of criminal proximity (‘facilitation’ of criminal conduct perpetrated by other individuals). The paper argues that the divergences between these two compliance-based mechanisms risk undermining the rationality of anti-mafia compliance while, at the same time, eroding the preventive vocation that characterises the corporate criminal liability system under 231 Legislative Decree.