Probation is the most frequently used disposition in juvenile court, and has become the primary alternative to youth incarceration in the past two decades. Yet research suggests that juvenile probation may be ill-equipped to meet the diverse needs of justice-involved youth. To address this gap, the Annie E. Casey Foundation began investing in probation transformation work, which aims to re-envision probation as a focused intervention that promotes positive behavior change and long-term success for youth who pose public safety risks. This report documents how two jurisdictions—Lucas County, Ohio and Pierce County, Washington—undertook probation transformation with technical assistance from the Foundation. Surveys of probation staff members and interviews with court and community-based stakeholders suggest that diversion, case management, family and community engagement, and racial and ethnic equity and inclusion are critical components of successful transforming juvenile probation.