This article explores Head Start's overall effectiveness in improving school readiness outcomes and its potential to reduce gaps in these outcomes in light of changing program goals, resource and funding capacity, and the demographic changes in the low-income child population it serves. Although not an explicit goal of the Head Start program, we assess whether and how the program can address reducing school readiness gaps between children of different racial and ethnic backgrounds and income groups. Because of changing policy priorities and targeting vulnerable groups of children with diverse needs, meeting Head Start goals within funding constraints can be challenging. Yet, as we will show in this paper, the program has successfully adapted to its changing environment, and despite the evolving nature of its goals and populations served, it has managed to demonstrate a favorable impact on children. Future research on tailored programming, program implementation and impacts on specific groups of children is needed to help Head Start further improve its ability to address persistent school readiness gaps.