This research explores the systemic and structural barriers affecting the effectiveness of community schools, particularly in providing mental health services and support, with a specific focus on how principals have responded to these needs in the post-COVID-19 era. Employing qualitative methods, including focus groups with principals from schools implementing the community schools' model, the study identifies three major themes: difficulties with lead agency collaboration and coordination with host schools, systemic and structural barriers to effective functioning, and holistic approaches to enhancing student support and well-being with mental health. Difficulties with lead agency collaboration and coordination reveal how inadequate communication and misaligned expectations between schools and external agencies hinder the effective implementation of mental health programs. The research highlights the impact of bureaucratic hurdles and policy misalignments on community schools' ability to provide timely and comprehensive mental health support. Systemic and structural barriers identified include inadequate funding, high staff turnover, and insufficient training for site coordinators. These barriers disrupt the continuity of care and limit the capacity of community schools to address the diverse needs of students effectively. Holistic approaches to enhancing student support and well-being emphasize integrating mental health services with a broader focus on the whole child. This approach aligns with The Whole Child Theory, which advocates for addressing all aspects of a child's development, and Critical Race Theory (CRT), which underscores the need to address systemic inequities impacting marginalized communities. The research aims to explore how principals of community schools have adapted to and addressed the mental health and well-being needs of their students in the post-COVID-19 era, offering a nuanced understanding of their responses to evolving challenges. The study provides recommendations for addressing these challenges, including advocating for increased funding, streamlining administrative processes, aligning policies with community school needs, and strengthening partnerships with community organizations. By adopting a collaborative and holistic approach, educational leaders can improve the effectiveness of community schools, ensuring equitable and comprehensive mental health support for all students. This study contributes to the field of educational leadership by integrating The Whole Child Theory and CRT into the analysis of community school challenges. It offers actionable insights for policymakers, school administrators, and community partners to enhance student support and well-being, fostering a more inclusive and effective educational environment in the post-COVID-19 era. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]