There is a well-documented need for leadership personnel who are prepared at the doctoral level to fill special education faculty positions at institutions of higher education (IHEs) and train the next generation of teachers. The intersection of continued retirements of special education faculty, shortage of well-prepared special education faculty to fill those positions, and changing preK-12 student demographics provides unique challenges to special education doctoral leadership preparation programs. Although a variety of variables influence special educator preparation in 21st-century schools, five contemporary issues (i.e., changing roles, evolving diversity, need for funding support, situating doctoral trainees in teacher training, and training delivery models) rise to a level highly relevant to special educator preparation at the doctoral level. In this article, the authors explore this complex landscape and offer policy recommendations to strengthen and update special education higher education leadership preparation.