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Police diversionary strategies such as formal police cautioning are extensively used in Australia to channel young offenders from the potentially harmful effects of formal court processing. Labeling theory provides the theoretical basis for diversion by predicting that – all other things being equal – diverted young people should be less likely to re-offend. Results from prior studies have thus far been consistent with these tenets of labeling theory, indicating that diverted young offenders have lower rates of re-offending than those processed by youth courts. However, little attention has been paid towards whether diverting young offenders at subsequent points of contact may nullify the potential ‘harm’ caused by prior formal court processing. This possibility is tested using a longitudinal cohort of youth offenders from Australia (n = 8,031). Re-offending is examined across four groups of young offenders based on their first and second contacts with the criminal justice system: (1) diverted-court; (2) court-court; (3) diverted-diverted, and (4) court-diverted. The study employs a quasi-experimental design using propensity score matching to account for pre-existing differences between the four groups.