In this qualitative case study of a district-led, school leader preparation program in Tennessee during the 2021-2022 school year, I sought to reveal district stakeholder perceptions using an open-ended questionnaire, on the design, possible benefits, and possible challenges of the district's Associate Principal Program. For this study, questionnaires were sent to four district stakeholder groups: district leaders, school leaders, associate principals, and teachers. After reading and synthesizing 37 responses from district stakeholders along with analyzing the district's Associate Principal Guidebook, Associate Principal Monthly Collaborative 2021-2022 agendas, and the Associate Principal Summer Retreat 2021-2022 agenda, three themes emerged regarding stakeholders' perceptions of the Associate Principal Program.The first theme was a need for more intentional recruitment strategies in the design of the Associate Principal Program in order to better build leadership capacity. The second theme focused around how the Associate Principal Program provided benefits for the school district, schools, and associate principals, such as extra administrative support and job embedded leadership experience for associate principals. The final theme focused around challenges of the Associate Principal Program for the school district, schools, and associate principals; these challenges included associate principal attrition and the design of the Associate Principal Program that required a new associate principal every three years at each school. This study was foundational and could be used as the framework for future studies exploring district-led, school leader preparation programs. [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.]