This paper examines the distinctive features of the Italian legal system in addressing criminal infiltration of businesses operating within lawful markets. Over time, Italian law has developed regulatory mechanisms that are often unique in the comparative landscape and may, in this respect, offer valuable insights for other jurisdictions. The paper proposes to introduce, within the anti-mafia framework, a system of preventive oversight capable of intervening at an earlier stage than the anti-mafia measures currently in force, which primarily target already entrenched forms of infiltration. This strategy draws inspiration in particular from the cooperative compliance model developed in tax law (Legislative Decree No. 128/2015). Its objective is to equip public authorities and undertakings with tools to identify risk indicators and to implement appropriate safeguards that may prove genuinely effective from a preventive standpoint. Particular attention is also devoted to the potential coordination, in the context of criminal infiltration, between this preventive approach and the system established by Legislative Decree No. 231/2001 on corporate liability. Finally, the study explores how ex post and ex ante control mechanisms may be balanced so as to preserve business continuity while enhancing resilience against criminal infiltration. The ultimate aim is to reduce reliance on punitive intervention and to ensure effective protection of the economy through the prevention of criminal infiltration. The central challenge lies in achiev-ing this objective through a multidisciplinary approach, integrating legal, economic, and sociological expertise.