Background/Context: Parent involvement in education is widely recognized as important, yet it remains weak in many communities. One important reason for this weakness is that urban schools have grown increasingly isolated from the families and communities they serve. Many of the same neighborhoods with families who are disconnected from public schools, however, often contain strong community-based organizations (CBOs) with deep roots in the lives of families. Many CBOs are beginning to collaborate with public schools, and these collaborations might potentially offer effective strategies to engage families more broadly and deeply in schools. Purpose: This article presents a community-based relational approach to fostering parent engagement in schools. We investigated the efforts of CBOs to engage parents in schools in low-income urban communities. We argue that when CBOs are authentically rooted in community life, they can bring to schools a better understanding of the culture and assets of families, as well as resources that schools may lack. As go-betweens, they can build relational bridges between educators and parents and act as catalysts for change. Research Design: Using case study methodology, we studied three notable school-community collaborations: the Logan Square Neighborhood Association in Chicago, Illinois; the Camino Nuevo Charter Academy in Los Angeles, California; and the Quitman Street Community School in Newark, New Jersey. Each case represents one of three types of collaboration identified in previous research: community service, community development and community organizing. Findings: Although differences in context mattered, we found three common dimensions of parent engagement work across the cases. The three core elements of this community-based relational approach are (1) an emphasis on relationship building among parents and between parents and educators, (2) a focus on the leadership development of parents, and (3) an effort to bridge the gap in culture and power between parents and educators. We contrast this community-based approach with more traditional, school-centric, and individualistic approaches to parent involvement. Conclusions: There are a number of lessons from this study for educators interested in broadening and deepening parent participation in schools. First, educators can benefit from taking a patient approach, building relationships over time. Second, schools may not be able to do parent engagement work alone; they can profit from the social capital expertise of community-based organizations. Finally, educators would benefit from understanding that communities bring different needs, aspirations, and desires to their children's education. If educators collaborate with community partners and help to develop parent leadership, they can form initiatives that meet the interests, values, and capacities of any particular school community.