This chapter examines the contradictions of the regime progression system within Brazil’s penal execution model, highlighting how its importation from the Global North has deepened the structural crisis of the country’s prison system. By combining socio-legal analysis and empirical data, the authors show how the principle of progression—originally intended to ensure a gradual path towards social reintegration—has been distorted by punitive practices, judicial discretion, and institutional neglect. The study argues that rather than solving the prison crisis, the progression model contributes to legal uncertainty, reinforces inequalities, and reveals the colonial foundations of penal governance in Brazil.