This chapter presents an in-depth case study of San Andrés Prison as an empirical context for examining the application of Identity Restoration Theory within a culturally distinct correctional environment. Drawing on qualitative data derived from doctoral fieldwork, interviews, and community engagement, the chapter analyzes how incarceration intersects with cultural displacement, educational exclusion, and identity fragmentation among Raizal inmates. Comparative analysis with regional and international correctional models highlights both the limitations of standardized punitive frameworks and the potential of culturally responsive educational interventions. The chapter examines narratives of transformation emerging from educational participation, emphasizing the role of cultural recognition, reflective learning, and community connection in fostering agency and moral reconstruction. Empirical findings are situated within broader discussions of desistance, restorative justice, and prison education research. Grounding Identity Restoration Theory in lived institutional experience, the chapter demonstrates how culturally anchored education functions as a mechanism of identity repair and offers evidence-based insights for policy and practice in island and postcolonial correctional contexts.