This cluster-randomized efficacy trial evaluated the impact of the Ready for Wages intervention, a classroom-based social skills program designed to improve the employability of youth living and being educated in juvenile justice settings. Fifteen juvenile justice facility schools participated. Data were collected from 118 classrooms: 59 treatment and 59 business-as-usual control. There were no statistically significant differences across conditions on the outcome measures, although differences favored the intervention group. Implementation was hampered by challenges associated with conducting research in authentic juvenile settings during the COVID-19 pandemic. Only half of the planned data collection could be completed. Despite the null findings of this study, more research in juvenile justice facilities is warranted to identify evidence-based practices that support prosocial behavior. Group intervention offers a cost-effective approach to reducing recidivism in a very high-risk population, with potential benefits for individuals and society in general.