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While criminologists frequently demonstrate interest in dispositional factors that contribute to offending, little work considers the potential turning points during probation supervision that may lead to desistance. This is especially important for juveniles incurring formal charges, as this population is susceptible to entering the adult system. Using a unique (due to access restrictions) dataset of probation officer case notes and case disposition/outcome data for 259 juvenile probationers in one jurisdiction, this analysis explores elements of the life course of juvenile clients under supervision. Researchers use case note data for an average of 3.65 years per client to develop life history plots of juveniles’ time on probation and between supervision terms. The life history/event data includes probationer behaviors, probation officer use of sanctions, receipt of probation violations or detention, and other life events. Findings suggest that probation officers use sanctions more frequently than rewards and time between client behaviors and receipt of consequences is delayed. Moreover, certain client behaviors make some clients more likely to incur probation violations and/or detention. Findings provide implications for the types of rewards and sanctions and case management practices that may be most helpful for promoting success on probation and post-supervision.