Whole school restorative practice (WSRP) calls for creating supportive, equitable schools, requiring broad systems change. This case study explores the journeys of three schools piloting WSRP in one Midwestern district and examines how school leaders designed and implemented within their school contexts. Schools were purposefully selected from within a three-year pilot project; data sources included annual interviews and focus groups with school leaders, and annual school reports. Each school developed a leadership team comprised of administrators and other staff who were knowledgeable of and committed to restorative justice principles. While grounded in common restorative principles, language, and approaches as part of their district's pilot project, school WSRP leaders simultaneously developed contextually-specific practices, including tailoring to learners' developmental stages. Overall, this study highlights the influential role of school leaders in navigating complexities that arise when working from a worldview that values human relationality and interconnection. Impact Statement: In this case study, school leaders' design and implementation of whole-school restorative practices (WSRP) reflected school-level contexts, including students' developmental stages, in alignment with restorative principles and values. Overall, this study highlights the influential role of school leaders in navigating whole-school change toward a worldview that values human relationality and interconnection. This study may inform how school psychologists, who often play a critical role in leading systems change initiatives in schools, can leverage their skills, knowledge, and experiences as part of WSRP leadership and implementation efforts.