Purpose: Improving urban schools of color and the communities where they are located requires leadership that spans school and community boundaries. The purpose of this study is to understand how principal and community leader actions support urban school reform along with community development at two community schools in the urban Midwest and Southeast. Research Method: Using a cross-case study design, this research draws on interviews, school-community observations, and document analysis. Concepts from community development leadership and cross-boundary leadership are joined to theoretically frame this study and guide the analysis. Data analysis was conducted using the constant comparative method. Findings: Leader actions varied across the two research sites based on the specific school-community tasks that were undertaken. However, cross-case findings suggest that leaders developed a broad vision for school and community, positioned the school as a spatial community asset, championed community causes at the school, and changed school culture. Implications: This approach to educational leadership highlights principals who purposefully work with community leaders toward mutually beneficial school and community outcomes. The study concludes with implications for leadership practice and future research.