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This study examined the intricate relationship between personality traits, access to prosocial turning points (pivotal moments that lead individuals away from a life of crime), and the likelihood of recidivism among juvenile offenders. Drawing upon social learning theory, life course perspectives, and the age-graded theory of crime, the research aimed to unravel how individual personality traits, shaped by environmental influences, interact with pivotal life events such as marriage and employment to either perpetuate or deter criminal behavior. While prior literature has established links between specific personality traits like impulsivity and recidivism and identified turning points such as education as catalysts for desistance, this study bridges these domains through the lens of Structural Equation Modeling (SEM). By analyzing data from the Incarcerated Serious and Violent Young Offenders Study (ISVYOS), the study examined the relationship between juvenile offenders' personality traits and their likelihood of reoffending after custody, exploring how this relationship is mediated by their access to turning points. The findings hold implications for tailored interventions and support services, shedding light on pathways to successful rehabilitation and reintegration for juvenile offenders.