Chronic insomnia can lead to depression, anxiety, cognitive difficulties, workplace absenteeism, underperformance, and high employee turnover as well as medical issues such as Alzheimer's, hypertension, myocardial infarction, obesity, and diabetes. Researchers have argued that healthful sleep is the most important factor in predicting longevity over diet, exercise, and heredity. Previous studies consider insomnia but do not address the specific issue of the levels of insomnia experienced by school principals and superintendents in Missouri. The purpose of the study was to investigate the levels in school administrators based on gender, age, ethnicity, experience in the current role, the level of professional role, the size of district and school, socioeconomic status of the district, socioeconomic status of school and type of school setting. Using the Survey Monkey online service, a two-part survey was e-mailed to 2,936 principals and superintendents listed in the Missouri Department of Elementary and Secondary Education School Directory (Missouri, 2016). The survey was comprised with a measurement to obtain the Insomnia Severity Index (ISI) and a demographic questionnaire. The survey response rate was 28.3% (n = 874). The findings show that insomnia scores differed between genders with female principals having significantly higher insomnia scores compared to male principals. Insomnia scores also differed across age groups, revealing that principals between 41 and 50 years of age had significantly higher insomnia scores than principals 51 years and older. In addition, insomnia scores differed across school settings, which revealed that principals managing urban schools had significantly higher insomnia scores than those managing rural schools. Insomnia scores did not differ significantly across any of the factors concerning superintendents nor in comparisons between principals and superintendents. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]