Opportunities for community service are integral to many international schools (ISs), aligning with their mission to foster social responsibility. This research, rooted in experiential learning theory and service learning frameworks, examines the experiences of four educators in ISs leading service programs. Findings suggest that service learning programs in international schools face logistical challenges, particularly regarding time constraints and risk and cost management. Teachers struggle with limited planning and implementation time. Recruiting staff and overcoming internal organizational barriers also pose difficulty. Embedded school and community cultures can further complicate these initiatives. Despite the challenges, educators report substantial personal and professional growth, including enhanced interpersonal connections and shifting perspectives. Adaptive, distributed, and servant leadership models may address the challenges and enrich the rewards that educators experience. The research will inform the future development of a model of service leadership in IS contexts.