This paper analyses the recent evolution of the so called ‘dual track’ system governing prisoners convicted of organised crime offences, established by Articles 4-bis and 41-bis of the Italian Penitentiary Act. Specifically, Art. 4-bis sets out a differentiated and more stringent framework for access to prison benefits. Art. 41-bis allows the suspension of ordinary prison rules and the imposition of severe restrictions in order to prevent contacts with the outside world. Conceived as exceptional instruments, these regimes have progressively stabilised within the system, recalibrating the balance between security and fundamental rights in the context of organised crime. The analysis focuses on three areas in which this transformation is most evident: access to prison benefits, the role assigned to restorative justice, and the protection of the right to intimate relationships within detention. Recent legislative and judicial developments have reshaped each of these dimensions, redefining the conditions and mechanisms of application both for prisoners subject to Art. 4-bis and for those placed under Art. 41-bis. Taken together, these dynamics reveal an internally incoherent model in which prison treatment acquires a predominantly symbolic and emergency-driven function, ultimately undermining the constitutional principle that punishment must be individualised.