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Research has identified multiple predictors associated with teacher retention; however, few studies have investigated the association between person-organization fit and teacher retention. The purpose of this study is to investigate the association between several measures of person-organization fit and teacher retention. The authors utilized a longitudinal data set that included 159 first-year teachers (FYTs). Data analysis identified that a FYT’s fit with their teaching colleagues was the strongest predictor of teacher retention. Additionally, that this predictor was stronger than several school and teacher characteristics as well as principal observation and teacher mentoring variables. The findings suggest that schools and districts should consider professional development to build the fit between FYTs and their teaching colleagues.