In the last decade, the number of public school students in the United States experiencing homelessness has more than doubled. Research shows that school enrollment processes are particularly onerous for families experiencing homelessness; yet, school choice and enrollment policies are rarely designed with the type of flexibility needed to be responsive to their multifaceted needs. In this study, we used in-depth interviews to explore the school-choice experiences of families living in shelters in New York City and to examine the knowledge and perspectives of shelter-based staff working with these families. We find that despite the New York City Department of Education's efforts to increase information provision, resource distribution, and monitoring of applications, families experiencing homelessness remained confused and frustrated by school-choice and enrollment processes. Moreover, their necessary focus on securing permanent housing, employment, and meeting their families' basic needs often limited the time they could spend searching for schools that matched their expressed preferences for an educational setting for their child. For their part, shelter staff viewed school choice and enrollment as another administrative burden added to an already extensive set of professional responsibilities, and they lacked sufficient information and training to serve as effective school-choice counselors for the families in their caseload. Taken together, our results highlight the wide-ranging, sometimes competing demands families and shelter staff living and working in the midst of multiple public systems encounter and the prioritization that must occur to comply with regulations and requirements.