This qualitative study in a Midwestern US city examines how school and community-based organizations support homeless students' connections to education-related resources and relationships. Drawing from organizational brokerage theory, which delineates how individuals' chances to thrive are shaped by the organizations in which they participate, the study finds that brokerage practice unfolds and is affected by variables at three specific levels. First, social workers, teachers, and principals at the "individual school" level arranged for registration, enrollment, and other immediate connections for students. Second, "school district"-level actors played key roles in orchestrating homeless students' transportation and educators' professional development across the city. Third, a range of "neighborhood factors"--including immigration and housing trends--affected the ways and extents to which organizations identified and supported homeless students. The study concludes by presenting several implications for research and practice.