Rates of homelessness are worsening in the United States, with a third of individuals experiencing homelessness being families with children. These families face many challenges, including limited social supports, insufficient access to services, and mental health concerns. These challenges inform a nuanced worldview, leading parents experiencing homelessness to understand their child’s school life in unique ways. The purpose of this study is to explore how parents experiencing homelessness understand their children’s participation in Head Start and publicly funded 4 K programs. We utilized semi-structured interviews with parents of 4 K students and applied an iterative approach for analysis to identify emergent themes and concepts. Results suggest families enter homelessness through several avenues and struggle with many aspects of homelessness, including stigma directed at parents and children. Parents identified many strengths in their children’s school programs, including education and support from faculty, as well as areas for growth, such as more comprehensive transportation and meal services. Overall, these results suggest families experiencing homelessness encounter many barriers to finding stable housing. Additionally, parents of children experiencing homelessness value their child’s education and access to resources in schools while still fearing the potential for their child to experience stigmatization and discrimination in schools. (author abstract)