This comparative case study concerns the daily work of community school coordinators and the challenges that they face. Informed by a conceptual framework based on organizational boundary spanning and systems theories, the authors analyzed transcripts from time study responses, structured interviews with school leaders, and documents from three community schools over a period of three years. The results reveal that community school coordinators work across organizational boundaries and face tensions presented by complex authority structures and inconsistent funding. The article concludes with guidance for current researchers, practitioners, and policymakers interested in community-based school reforms.