ABSTRACT Elementary school principals play a central role in inducting families into their school communities. As early childhood programs, such as prekindergarten, increasingly become part of elementary schools, this role is expanding. Yet, principals often struggle to establish and maintain such relationships, particularly with many of the historically disenfranchised communities that prekindergarten programs are often designed to serve; these struggles are troubling because success in the early years of schooling can lead to sustained and positive impacts for students as they progress through schooling. Furthermore, few studies have investigated this issue. In this article, we do so by employing Yosso’s Communities of Cultural Wealth to examine how a collection of principals working in Texas described their interactions with the children and families as they entered the early grades of their schools and what these principals hoped these children and families would gain from their early childhood education programs. Our findings revealed strengths and growth areas in their descriptions of fostering the cultural wealth of the children and families entering their schools, which provides an opportunity to consider how to support and train principals as well as the structural changes that need to be addressed to support principals in these activities.