The primary objective of probation supervision is to ensure compliance with probation conditions, improve public safety, and rehabilitate and reintegrate offenders back into a pro-legal and social lifestyle. However, statistics in Kenya point to consistently high rates of recidivism in the past two decades. Despite this, limited information exists on the effect of juvenile supervision practices on recidivism in the country. This study aimed to evaluate the existing juvenile probation supervision practices and their outcomes in Nairobi County, Kenya. The study sampled 226 respondents comprising juvenile probationers and probation practitioners. Using a concurrent triangulation mixed-method approach, three probation supervision practices, namely, frequency and mode of supervision, supervision skills and workload, were examined. The outcomes for each of the three practices were varied, with frequency and mode of supervision having a reducing effect on recidivism but not significant. Supervision skills and probation officers’ workload significantly impacted recidivism. Collectively, the centrality of the existing probation supervision practices in curtailing juvenile reoffending behavior was evidenced. However, a number of challenges, including limited specialized training and mentorship in juvenile matters, resource constraints and overwhelming workloads, limited optimal outcomes. The study recommends consistent juvenile-focused training on supervision skills, clear guidelines to sustain manageable caseloads, and leveraging technology for administrative tasks and remote supervision.