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In this study of novice principals in Chilean public schools, we examined factors that contributed to the attrition, within their first three years in the post, of five of 13 new principals from the same region. All of these principals were serving in high-poverty schools that face multiple challenges, and the failure of a newly appointed principal only adds to those challenges. Although the study is located in Chile, principal turnover in high poverty schools is also a problem in other parts of the world (Burkhauser, Gates, Hamilton, & Ikemoto, 2011). Our purpose in this paper is to explore how principals explained the policy, organizational, and personal circumstances that shaped their own unsuccessful school leadership and eventual departures.