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This study explores the relationship between high school principal turnover and position held prior to the principalship. Most high school principals previously held a principalship or assistant principalship. Those who served as a principal in a different district are more likely to leave the focal high school. Of those who came from a different principalship, middle school principals from the same district are less likely and high school principals from a different district are more likely to leave the focal high school. Thirty percent of high school principals transition into administrative positions. Those who assumed a different principalship were more likely to move to a school with higher performing students.