Since its inception in 1837, the school superintendency has been the focus of significant attention from the educational research community. Superintendents face a wide spectrum of responsibilities that can challenge even the most prepared individuals. Fewer candidates are seeking the superintendency and the turnover rate for those already in the field is perceived by superintendents to be of concern. Stress associated with the superintendency has been shown to be a contributing factor to this turnover. This study investigated the alignment between personal and environmental factors and stress management of superintendents. Understanding the relationship between personal and environmental factors and superintendent stress, specifically the ability to predict this stress by evaluating the personal and environmental factors, is a first step in decreasing stress and extending superintendent tenure. The framework of this study is based upon the concept of person-environment fit (P-E fit), which has been widely studied as a means for conceptualizing organizational behavior, organizational psychology, and human resource management. This study uses a quantitative approach and survey research methodology with a postpositivistic theoretical perspective. Participants in this research study were 992 practicing superintendents in the Midwest. Five new superintendent stress constructs--board-relations stress, task-based stress, expectation-based stress, resource-management stress, and self-efficacy stress--were identified through a factor analysis. Hierarchical regression analysis results indicated that both personal and environmental factors predict frequency of superintendent stress. Implications for aspiring and practicing superintendents, superintendent preparatory programs, and superintendent support systems are discussed. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]