This article interrogates penal systems through the theoretical framework of institutional complexity and organizational hybridity, with a specific focus on the Italian penitentiary system. Drawing upon institutional theory and public management literature, we analyse how competing institutional logics of security, punishment and rehabilitation generate organizational tensions that can precipitate mission drift. The study furnishes a detailed analysis of the Italian penal system’s structure, operational challenges and comparative standing within the European context. Our findings indicate that the structural disequilibrium between security and rehabilitative functions, compounded by persistent resource limitations and overcrowding, has culminated in significant mission drift, deviating from the rehabilitative ideal enshrined in legislative provisions.