This chapter analyzes the relationship between prison education and the progressive loss of identity experienced by incarcerated individuals within punitive correctional systems. It examines how institutional environments characterized by control, standardization, and cultural disconnection undermine personal agency, self-concept, and moral coherence. Drawing on criminological theory, desistance research, and educational psychology, the chapter explores the paradox of prison education as both a potential site of transformation and a mechanism that can reproduce alienation when detached from identity, culture, and lived experience. Particular emphasis is placed on the limitations of utilitarian and compliance-based educational models that prioritize skills acquisition over meaning, reflection, and belonging. The chapter introduces Identity Restoration Theory as a response to these limitations, positioning education as a process of identity reconstruction rather than behavioral correction. By situating learning within the broader context of cultural memory, narrative repair, and moral agency, the chapter establishes a critical link between education, dignity, and sustainable reintegration, laying the groundwork for a restorative approach to rehabilitation.