Purpose: The objective of this study is to investigate and characterize principals' backgrounds, individual and school level factors associated with leadership stability, and principal career paths and exit behaviors in Missouri. Method: In this study, the authors construct two data sets of practicing school principals in the state of Missouri: (a) one consisting of approximately 2,700 school principals across grade levels for each year from 1999 to 2006, and (b) one consisting of three cohorts of principals who were new to a given school in 1999, 2000, and 2001. With the first data set, the authors construct "stability" ratios identifying the amount of time a principal spent in any given school as a percentage of the total time that principal was in the data set. With the second data set, the authors create indicators of the time period at which a cohort member (a) left the principalship altogether (in Missouri), (b) made a first move to another school, or (c) made a second move to another school. Using the first data set, the authors estimate truncated regression models to identify the relationship between principal characteristics, school context, and principal stability. Using the second data set, they estimate Cox Proportional Hazard models to determine the relationship between principal characteristics, school context, and exit or move behavior. Findings: The authors find that a principal's relative salary, compared to peers in the same labor market, exerts a consistent influence on stability--the higher the salary, the more likely a principal is stable and less likely he or she is to move to another school. Principals were able to leverage school-to-school moves for an average change in relative salary of about +5%. The authors also find that school racial composition--specifically percentage of students who are Black--may lead to instability and greater likelihood of a second move and that middle school principals are less stable. (Contains 7 tables, 1 figure and 3 notes.)