This chapter examines learning disabilities, literacy barriers, and unmet educational needs within incarcerated populations and explains how these conditions shape identity, agency, and rehabilitation outcomes. It explores how undiagnosed cognitive differences, disrupted schooling, and trauma-related impairments limit academic engagement, self-confidence, and moral development. The chapter connects educational failure inside prisons to earlier experiences of exclusion, misrecognition, and cultural dislocation. It presents assessment strategies that identify learning profiles, literacy gaps, and neurocognitive challenges as a foundation for effective educational intervention. The discussion emphasizes inclusive instruction, individualized learning plans, and culturally grounded pedagogy as essential components of meaningful prison education. Through the framework of Identity Restoration Theory, the chapter demonstrates how educational recognition strengthens dignity, restores agency, and supports sustainable reintegration.