The purpose of this qualitative study was to examine the challenges professors of educational leadership encounter as they prepare aspiring principals to be instructional leaders. Drawing upon an open-ended questionnaire and semi-structured interviews of professors from across the U.S.A., we analyzed significant statements and created themes that illuminate the challenges facing university faculty in preparing aspiring principals for instructional leadership. From the analysis of the combined data sources, five overarching challenges emerged for preparing future principals for the role of instructional leader. These challenges are: (a) teaching instructional leadership via online courses, (b) time in the internship to focus on instructional leadership, (c) instructional leadership mindsets, (d) pedagogical knowledge for use in instructional leadership and (e) the professor's knowledge/experience in instructional leadership. The five challenges presented in the findings highlight the need for continuous program evaluation and collaboration among faculty to address coursework both in the classroom and in the internship. Additionally, the challenges highlight the need for more research in how to prepare aspiring principals to be culturally responsive and adopt a growth-mindset when it comes to teacher development, and how to create powerful learning experiences for aspiring principals in varying program contexts.