This study examines the impacts of Chicago's Universal Pre-K (UPK) expansion on the operational dynamics of preschools across setting types from the perspective of administrators. Specifically, we explore how Chicago Public Schools (CPS) principals and and Community-Based Organizations (CBOs) directors experienced the implementation of UPK. Analysis reveals nuanced experiences of UPK's expansion, common challenges, and administrator's savvy in navigating these new waters. This poster highlights two significant challenges -- shifting funding streams and fluctuating enrollments -- and explores the strategic paths charted by administrators over the past four years to navigate the Chicago Early Learning initiative.