Background/Context: This study contributes to the literature on the schooling of homeless and highly mobile students. Although previous work has detailed the demographics of homelessness, the effects of homelessness on academic progress, and particular legal issues in homeless education, this research focused on how individual and institutional relationships influence homeless education. Purpose/Objectives: The purpose of the study was to develop deeper understanding of how schools and shelters helped create educational social capital for students and families who were experiencing homelessness. The guiding research questions for the study were: (1) How do school and shelter leaders perceive social capital as influencing the education of students who are homeless? and (2) How do school and shelter leaders' relational networks influence the education of students who are homeless? Setting: Data were collected from three homeless shelters and three public schools that are located in a large city in the Mid-Atlantic region of the United States. Participants: A total of 31 interviews were conducted with shelter-based administrators, case workers, and child development specialists, and school-based principals and central office administrators. Research Design: A qualitative collective case study research design was employed. Findings: Homeless students and families appeared to have insufficient stores of productive social capital, and although schools and homeless shelters provided them with some important relationships and resources, school and shelter leaders' own shortages of bridging social capital limited the extent to which efficient educative active could occur. Conclusions/Recommendations: Based on the findings, it is suggested that schools and shelters prioritize social capital development and improve interorganizational networking. Specifically, purposeful efforts should be made to develop school-shelter-family networks that are heterogeneous in composition.