Outcomes-Based Contracting (OBC) ties vendor payments to performance metrics, aiming to enhance accountability in public education. This study examines its implementation in tutoring services through the Southern Education Foundation pilot program. Interviews with district leaders and vendors reveal that OBC fosters collaboration, improves service alignment with student needs, and enhances data tracking. However, financial risks for vendors and the complexity of implementation pose challenges. While OBC shows promise in strengthening district-vendor relationships, its broader adoption requires capacity building, equitable risk-sharing, and further research on long-term student outcomes.