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Successful reintegration of ex-offenders into society is vital to preventing recidivism and ensuring that ex-offenders contribute meaningfully to society, especially in developing countries. However, limited research has focused on investigating potential challenges that can hamper a successful re-entry of ex-offenders into the community and how they can be addressed. The current work contributes to filling this lacuna in knowledge by investigating whether ex-juvenile offenders in Ghana have challenges with reintegrating into society. The study addresses the following questions: In Ghana, do ex-juvenile offenders face challenges with re-entering into the community, and if “yes,” what are these challenges, and how can they be addressed? This study is based on desistance theory and qualitative data from in-depth semi-structured interviews with ex-juvenile offenders, prison officers, social workers, academics, and organizations working on reintegrating juvenile ex-offenders. The current work indicates that ex-juvenile offenders face multiple challenges, including community stigmatization, continued parental/familial neglect, and lack of basic necessities of life (especially housing and food), employment, education/training, and mentoring. Theoretical, policy, and practice implications for addressing reintegration challenges, especially in the sub-Saharan African context, are considered in the conclusion section.