In the United States (U.S.), the heart of public education lies in the commitment to providing every child with the necessary resources for their learning and development. Today, in 2024, principals are responsible for ensuring all students have equitable access to education by integrating technological advancements, maintaining a rigorous curriculum, and fostering a safe and healthy environment. Given these substantial responsibilities, principals must continuously develop their leadership skills through ongoing continuous professional development (CPD). My study examines the experiences of U.S. public school principals in engaging with continuous professional development (CPD) as a tool for professional learning growth, meeting the needs of multiple stakeholders, and focusing on positive student outcomes. Through a qualitative, multiple-case study approach, I explored the perceptions and experiences of four Connecticut public school principals, using Situational Leadership Theory (SLT) and Adult Learning Theory (ALT) to underscore the importance of diverse leadership styles and personalized CPD. The multiple case study includes in-depth interviews and has case participants from across different socio-economic contexts (District Reference Groups); I also utilized the Portraiture methodology to assist in understanding the participants on a humanistic level. Findings reveal a link between quality CPD and participants' perceptions of its impact on student outcomes, highlighting the need for practical, job-embedded experiences, collaborative practices, and ongoing supportive coaching. Themes of personal and professional growth, strategic management, and creating supportive environments emerged. Principals emphasized the significance of networking, collegial conversations, and data-driven strategies for staff and student support to assist in meeting the demands of the position. While participants generally felt supported by their direct supervisors, they identified several challenges associated with navigating CPD amid other responsibilities: time constraints, demands, a sense of professional isolation, and the perceived relevance of CPD were noted by participants as significant barriers to fully accessing quality professional development. The findings suggest that a variety of measures are needed to improve CPD for public school principals, including fully funded federal mandates, evaluation of unfunded state mandates, and the development of effective CPD plans to address these challenges. These recommendations are aimed to empower principals, foster positive school cultures, and improve student outcomes. [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.]