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Juvenile courts across the country continue to address delinquency in a manner that is largely inconsistent with adolescent developmental research. Probation remains the default disposition of the juvenile court, accounting for more than 50% of all juvenile court dispositions, though delinquency data would suggest that this level of intervention is not appropriate for most youth. Further, probation practice is often rooted in a punitive, authoritative approach, which is not effective with adolescents. The Annie E. Casey Foundation (AECF) has developed a framework for Probation Transformation which suggests that juvenile justice systems will achieve better outcomes for the system, youth and families by: 1) sharply reducing probation caseloads by diverting low-risk youth and substantially expanding diversion programming; and 2) transforming probation practices for higher-risk youth by consistently implementing “what works” and intensifying the focus on engaging families, building community partnerships, combatting racial and ethnic disparities, and providing positive youth development opportunities. This paper will examine the dissonance between adolescent developmental science and juvenile court disposition trends. This paper will also review lessons learned from AECF’s Juvenile Detention Alternative Initiative (JDAI) sites, including: a) gaps in services which leave developmental needs unattended for justice-involved youth; and b) practice improvements and innovations that seek to provide support and supervision in a developmentally appropriate manner.