Encouraging stable preschool enrollment is a critically important policy response for ameliorating the negative impacts of housing instability and homelessness on young children. To contribute to the evidence base for preschool and family support policies, this article investigates how housing instability and homelessness influences parental preschool choices. Using a modified grounded theory approach to analyze transcripts of interviews and focus groups with 28 families who had experienced homelessness, we find that for formerly homeless parents, the most important factors influencing preschool enrollment are housing stability, social networks, attitudes about preschool education, history of trauma, and the type of support received during interactions with social service systems. We integrate these findings into a socio-ecological model that can guide the development of policy responses that encourage preschool enrollment among families experiencing homelessness. (author abstract)