This qualitative study examines the collaboration and leadership practice that influences the education of homeless students in a large Mid-Atlantic city. The perspectives of administrators and staff members from three homeless shelters are analyzed with insights from Spillane's (Distributed leadership, 2006) distributed leadership theory. Findings from the study indicate that differences in shelter and school structures and cultures present significant obstacles to productive communication that would facilitate homeless children's schooling. Several structural and programmatic recommendations are made towards developing more effective leadership practice among schools and shelters.