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The evolving role of today’s school leader is an important consideration for preparation programs tasked with equipping future principals with the tools to meet the needs of special populations of students. Despite increased accountability policies aimed at ensuring all students are receiving an adequate education, the extent to which a new generation of principals are prepared for these new responsibilities remains unclear. The purpose of this qualitative study is to examine the experiences of 24 principal interns in a 15-month residency preparation program designed to develop the skills to advocate for special populations. Participants reported a sense of readiness when it comes to the challenges associated with leading special populations which they attributed to particular aspects of the training.