This research examines the experiences of juveniles involved in a juvenile justice diversion program in Southern Indiana, specifically focusing on participant motivation, experiences, and program outcomes. Using a qualitative comparative case study approach, this study assesses the differences and similarities of experiences between families in two different treatment programs and the impact this program had on the students’ academic and behavioral outcomes during their final year of high school. Interviews with families and participants, as well as descriptive data from student educational records, provide insight into the experiences that stakeholders have in the program, and highlight the need for developing relationships with service providers and school administrators. The program also serves as early intervention programs to interrupt further involvement in the court system. The findings call attention to the need for program improvement, including greater accountability and connection to the school and community, to provide a more robust diversion program with greater positive and long-lasting impacts for student and family participants. Recommendations are made for stakeholders including school administrators, student participants, and service providers that will have lasting impacts on students for many years to come. This research contributes to the discourse on successful juvenile justice diversion programs and promotes a model for other communities to replicate to strengthen the bond between students, families, schools, and communities, and interrupt the school-to-prison pipeline.