Encouraging children's academic success and positive outcomes is a critical duty of parents and school leaders. School leaders face a variety of challenges, including encounters with parents. The problem is the challenges school leaders face where parental involvement influences their children's holistic development. An absence of dynamic parental involvement in educational programs was demonstrated by the gap in the literature. The purpose of this qualitative case study was to explore the challenges school leaders face as it relates to the influence of parental involvement in educational initiatives that support children's overall growth and progress. The theoretical frameworks are distributed and transformational leadership. Three research questions were drafted and designed to gather information from school leaders and parents. These research questions were derived from the problem statement. Purposeful sampling was used to gather data from 30 participants, including 15 school leaders and 15 parents in South Carolina. Data was collected via a questionnaire via Google Forms and coded using Excel spreadsheets and MAXQDA. The body of knowledge regarding school leaders' challenges in promoting parental involvement in school activities was expanded by adding historical district data, original questionnaires, and empirical evidence. School leaders and parents' shared experiences and perspectives were combined into nine themes, emphasizing the need for collaborative efforts to help students reach their full potential and work assiduously to mitigate the existing barriers. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]