This investigation assesses the relationships of the following variables with Iowa high school principals' level of job satisfaction: (a) size of school, (b) level of authority, (c) threats to job security, and (d) educational issues seen as challenges. Further, relationships between levels of authority, size of school, job security issues, and educational challenges were identified and analyzed. Data for this study were taken from an existing data set using the "Iowa Secondary School Principals' Status and Opinion Study" compiled in 1989 by the School Administrators of Iowa, Iowa State University, and the University of Northern Iowa;The population was all public secondary school principals (n = 450) in the State of Iowa. The sample consisted of the 253 high school principals (whose responsibility includes grades ten, eleven, and twelve) who responded to the survey. Twenty hypotheses were derived from research questions directing the study;Major findings of this study center around level of job satisfaction. Most Iowa principals are very satisfied. The size of school significantly relates to level of job satisfaction. Principals of larger schools reported being more satisfied. Level of authority also significantly relates to level of job satisfaction. Principals reporting a higher level of authority also reported a higher level of job satisfaction. Five of nine threats to principal's job security significantly relate to job satisfaction. Twenty-two educational issues significantly relate to job satisfaction. All five of the educational issues categorized as "relationship" issues significantly relate to level of job satisfaction. This did not happen in any of the four other categories of issues;Generally, principals rating their level of job satisfaction as "not satisfied" also report being challenged the most by significant threats to job security and educational challenges. Principals rate their level of authority as being very high. Two education issues: "shared employees" and "central office involvement in school building decisions" significantly relate to level of job satisfaction, level of authority, and size of school. Principals report "alcohol use by students" as the most challenging educational issue. Size of school significantly related to two threats to job security and thirteen educational issues. No definite pattern relating to size emerged.