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Districts are examining their Assistant Principal (AP) to principal pipelines to fill looming principal vacancies. In this qualitative study in one large urban district redesigning its principal pipeline, we relied on interviews; a principal focus group; and an observation of AP professional development, to explore the learning and development experiences that support APs’ growth and the barriers that hinder their growth. Our findings revealed that intentional mentorship by principals, participation in a broad range of leadership roles at their schools, and individual motivation to take on additional responsibilities prepared APs for the principalship. APs’ varied access to learning opportunities and the lack of cohesion among differing types of learning opportunities emerged as themes and concerns from among project participants.