Education, or rather the absence of education past year ten, is a common characteristic of people serving a custodial sentence in Australia (Australian Institute of Health and Welfare [AIHW], Adults in prison, 2023). Correspondingly, education is seen as a protective factor that is essential in assisting people, in particular young people, to desist from offending and/or to re-engage in society (White et al., Improving educational connection for young people in custody, 2019). Education has also been identified as a “key tool in breaking the cycle of poverty, homelessness and recidivism” (Carey, Histories and philosophies of carceral education, 2022, p. 270). Clemente transformative learning approach develops critical thinking enabling the challenging of embedded values and belief systems (Gervasoni et al., Australian Journal of Adult Learning, 53(2), 253–279, 2013). In this chapter, we discuss the importance of education as a protective factor. In doing so, we explore the nexus of educational benefits and the potential for the Clemente transformative learning approach to aid incarcerated individuals to explore and potentially alter their own life narratives. Further, we discuss the benefits of engaging with education while in custody as a pathway to reengaging with society once the custodial sentence has concluded.