This thesis explores the experiences of formerly incarcerated individuals who have pursued or attained teaching roles in Ireland through adult education pathways. While education is widely promoted as a tool for rehabilitation and social reintegration, the journey from prisoner to professional teacher remains fraught with symbolic, institutional, and moral barriers. Grounded in a qualitative, phenomenological methodology, this study centres the voices of six participants five men and one woman who have transitioned from imprisonment into various educational contexts, including adult, community, and further education. Their accounts reveal how personal transformation, often catalysed by prison education and peer-led learning, collides with enduring stigma, opaque regulatory systems, and conditional inclusion within the teaching profession. Drawing on the work of Goffman, Maruna, Mezirow, Wacquant, Inglis, and Bates Evoy, the analysis traces three interwoven strands: stigma and identity, transformative learning, and institutional recognition. These themes illuminate how educational growth is often undermined by discretionary vetting processes, professional gatekeeping, and the absence of structural recognition. The study contributes new knowledge by addressing a gap in Irish and international research on post-prison access to regulated professions particularly teaching and reveals how adult education serves both as a site of empowerment and a space of subtle exclusion. Positioned within both academic and lived experience, this research offers a reflexive, critical account of what it means to seek legitimacy after incarceration. Its findings have implications for policy reform, teacher registration, vetting transparency, and inclusive adult education practice. Ultimately, it asks whether the Irish education system is truly prepared to recognise transformation or whether it remains bound by symbolic boundaries that deny full professional belonging to those who have already changed.