This paper examines the complex relationship between corruption and organised crime in contemporary Italy, with particular focus on infiltration of public procurement systems. Despite sophisticated anti-mafia frameworks and criminal law instruments, significant regulatory gaps persist, enabling organised crime to operate within the legal economy. Modern mafia organisations have evolved from predominantly violent enterprises into sophisticated entrepreneurial entities, strategically penetrating public contracts through systemic corruption and collusive practices. The Italian legal framework suffers from structural deficiencies. The regulation of direct awards and cascading subcontracts frequently escapes bid-rigging rules; exemptions from mandatory anti-mafia verification below the €150,000 threshold create immunity pockets; and the abolition of the crime of abuse of functions (“abuso d’ufficio”) has eliminated a crucial prosecutorial tool. Criminal law instruments traditionally designed for formalised competitive procedures prove inadequate for addressing modern, informal procurement mechanisms. Outdated statutory provisions – particularly Arts. 353 and 353-bis of the Penal Code – lack sufficient contemporary terminology and flexibility. The analysis concludes that comprehensive legislative reform is imperative, modernising criminal law frameworks whilst maintaining rigorous adherence to principles of legality, coupled with enhanced investigative capacity and institutional coordination to address pervasive mafia infiltration in public contracting.