Following the COVID-19 pandemic, K-12 public school district superintendent turnover rates reached concerning levels in Oregon. This study explored relationships between superintendent longevity and superintendents' experiences with the school board, experiences in the school district, experiences related to their own health and safety, and experiences related to superintendent professional preparation and support. The study also examined themes between the superintendent performance evaluation and superintendent longevity. Data was collected from superintendents (n = 121) who served in Oregon's K-12 public schools at any time between the 2019-2020 and 2022-2023 school years. There was a statistically significant relationship between superintendents' positive experiences with the school board and superintendents' employment status at the end of the school year in 2022-2023. Post hoc explorations of survey responses revealed challenges related to (a) mental health and maintaining a healthy work-life balance, (b) the role of politics in school districts and influencing board members' actions, and (c) superintendent preparation programs. Nonetheless, superintendents were supported by state and local organizations and superintendent colleagues, reported positive professional relationships with school board members and employee associations, and felt that decisions made by the school board reflected the school district's vision and mission. These findings are discussed in terms of implications for superintendent training and recommendations for future research. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]