This study evaluates the effectiveness of Jamaica's Aspiring Principals Program, APP, administered by the National College for Educational Leadership, NCEL. The study is conceptually grounded in the Marzano School Leadership Model and the Tannenbaum Model of Training Effectiveness using a mixed-methods analysis of survey responses from 108 principals who are both APP and non-APP graduates in the seven administrative educational regions across the country. The study reveals that APP graduates demonstrate significantly higher confidence levels in principalship roles in navigating conflict management and decision-making than non-APP graduates. A regression analysis shows that APP participation positively influences job satisfaction, while extensive administrative responsibilities tend to decrease it. Overall, the findings emphasize the transformative impact of the APP on enhancing leadership confidence, conflict management skills, and job satisfaction, underscoring the importance of continued investment in principal preparation in Jamaica. The study underscores the critical need for policy reforms that integrate crisis management and adaptive leadership into the training of aspiring principals, ensuring that school leaders are well-prepared to navigate especially systems-altering occurrences like the COVID-19 pandemic. The study also encourages a licensing regime for principals, complemented by continuous professional development, to maintain high leadership standards and accountability. The findings emphasize the value of context-sensitive leadership preparation, advocating for a leadership preparation curriculum that blends theoretical knowledge with practical experiences tailored to the unique challenges faced by Jamaican school principals. [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.]