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This paper utilizes data from 2007–2008 Schools and Staffing Survey (SASS) Principal Survey and 2008–2009 Principal Follow-up Survey (PFS), sponsored by the National Center for Education Statistics (NCES). We comprehensively examined how principal mobility status can be explained by different factors. Except for principal characteristics and school demographic characteristics, we further examined the factors related to principal working conditions and job satisfaction, including principal autonomy, barriers to the dismissal incompetent teachers, faculty relationships, job worth, disciplinary climates, school safety, parental involvement, and problems occur at school. With Multinomial Logit Modeling, we estimated the impact of different factors on the likelihood of principal mobility choices—moving to another school, demoted, or leaving the school system.