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The overrepresentation of offenders with mental health conditions in the South Korean criminal justice system, coupled with persistent recidivism and the severity of offenses, has raised concerns about the limits of punitive responses. Nevertheless, research has largely focused on theoretical frameworks and case analyses from foreign contexts, leaving domestic case-level factors that shape reoffending trajectories understudied. Drawing on Ministry of Justice records, this study employed a qualitative comparative case design to examine how treatment experiences and social contexts influence recidivism among offenders subject to court-ordered treatment. Eight cases were analyzed across two groups – recidivism and non-recidivism, four cases each. Guided by Mandelbaum’s Life History framework, cases were examined across three domains – life areas, turning points, and adaptation – encompassing socio-demographic backgrounds, treatment experiences, and treatment outcomes. Findings reveal three interrelated factors associated with recidivism: individuals’ perceptions and attitudes of treatment, the presence or absence of family and community support, and motivation to improve life circumstances. These factors diverged across intervention stages – pre-treatment, in-treatment, and post-treatment – with recidivism cases consistently reflecting treatment disengagement and social isolation. These findings underscore the importance of structured treatment communication and sustained community support as critical components of reoffending reduction strategies for offenders with mental health conditions.