As the goal of building an even more inclusive early education and care system is still in sight, reflecting on the history of early education in New York City can bring perspective to its current challenges. Earlier this Spring, the Citizens’ Committee for Children of New York released The Youngest New Yorkers, a report examining the more recent history of early education and care in New York City and what barriers remain for families trying to access care. ICPH wanted to build on this foundational work to look even further back at the evolution of the City’s early education and care system alongside the trajectory of family homelessness, changes in public assistance, and provision of care and education. By tracking the history of the City’s efforts in this arena, it is possible to offer fact-grounded recommendations to policymakers focused on improving access to early education and care programs. Among the recommendations for system improvements that can best assist families experiencing homelessness are more data and increased transparency, as well as diminished administrative burden in application and enrollment practices that considers the unique needs of working homeless families. (author abstract)