The American family is changing (Brown, 2017; Pew Research Center, 2015; Seltzer, 2019). While grandfamily formations are becoming more common throughout the United States, they are particularly prevalent in specific counties of north-central Pennsylvania. Data obtained from the American Community Surveys between 2012 and 2021 suggest that incidences of grandparents raising grandchildren in this area have increased by 54% over ten years, with most of the children in these families between six and eleven years of age, which falls in the range of compulsory school attendance. Epstein et al. (2021) report that these family formations are often informal due to previous negative experiences with child welfare agencies, fear of jeopardizing relationships with their biological children or family members, and fears of government intrusion. The decision to avoid a legal arrangement complicates caregivers' ability to enroll a student in school, make educational decisions, or access the child in an emergency. Meanwhile, federal and state laws and local regulations constrain school leaders' responses to this growing population, establishing positional conflict where partnership is vital. This qualitative study, conducted with a constructivist worldview, utilized a critical phenomenology approach and portraiture methodology to present the lived experiences of grandparent caregivers and school leaders, focusing on the culture and systems that shape their circumstances. The realities of the participants, connected by their roles in the lives of the children, give voice to the experience of a growing population and the systems that must respond to these changes for the communities they serve. The data suggest that educators must build cultural competencies centered on their communities' unique composition. These competencies, essential to successful classroom and district leadership, require all stakeholders to assume and share the roles of leader and advocate within the school and external communities. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]