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Probation is often considered the “workhorse” of the juvenile justice system in its multi-role in serving multiple purposes for juvenile court. Given that most delinquency cases result in probation and the characteristics of those cases have fluctuated in recent decades, it seems important to the functioning of the juvenile justice system to understand what happens to youth placed on probation. The study involved examining administrative data collected on juveniles adjudicated to probation supervision under the auspices of a metropolitan county bureau. A total of 2,916 juvenile probationers fell within the study timeframe. Of these, 89% (n = 2,598) were age-eligible to be convicted of an offense as adults during the study timeframe as well. In total, 32% of the juvenile probationers in the sample reoffended during the study period. Interestingly, the more assigned case workers juvenile probationers had, the more likely they were to reoffend. In addition, certain programs the juveniles participated in while on probation increased their likelihood of reoffending. Characteristics of both the juveniles and the programs were examined as well. Strengths and drawbacks are discussed, as well as directions for future research.