Purpose: During the past two decades, principal turnover issues have raised nationwide concerns about leadership stability and student performance. With national data from National Center for Education Statistics, this study examines how principal working conditions influence the probability of different types of principal turnover (mover, promoted, demoted, leaver, and retired). Research Method: This study utilizes data from 2011 to 2012 Schools and Staffing Survey and 2012-2013 Principal Follow-up Survey, and performs multinomial logistic regressions with region fixed effects to examine how principal working conditions are associated with principal turnover, while controlling for principal characteristics and school context. Findings: This study finds that principals with beneficial job contracts, tenure system, and higher salary were less likely to transition. Additionally, positive disciplinary environment lowered the odds of principals moving to another school, especially in schools with high concentrations of students of color. Moreover, more influences on determining teacher professional development and budgeting were associated with lower odds of principals leaving education, but more influence on setting performance standards showed the opposite direction. Implications: This study could assist policy makers in providing positive working conditions to support and retain principals for long-term school improvement. Moreover, school districts could facilitate building positive school disciplinary environment to lower principal turnover in underserved schools.