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Recent research on principal preparation and professional development shows that both can have a positive influence on principals’ knowledge and skills, as well as their behaviors that influence the conditions for teaching and learning. However, most of the research on principal learning analyzes principal perceptions. Few studies have successfully linked principal learning to student outcomes. We utilized data from California that included approximately 400 principals and over 260,000 students. In this paper, we share findings from our regression analyses of whether student gains related to the quality of principals’ professional development. We found that the overall professional development quality index and each of the subcomponent factors were positively related to student gains in both English Language Arts and math.