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This study explored the factors that supported transition success for principals in an urban public school district in Alberta, Canada. Leadership transitions can be challenging for the principal and the school community, given that the leaders have little to no knowledge of the new school, culture, and staff. Research has suggested that a principal change can negatively impact teachers and students. Given the importance of the principal to a school’s performance, ensuring successful principal transitions is essential. Principals were surveyed and interviewed to determine what professional learning opportunities, resources, and/or supports helped with their transition experience. The results of this study have implications for principals and district leaders to support transitions to reduce the negative impact on student outcomes.