The purpose of this study was to investigate New York State school superintendent job satisfaction and the potential contributing factors to their job satisfaction in an era of reduced resources and increased accountability. This survey was sent to 684 superintendents throughout New York State and completed by 280 superintendents. Sharp, Malone and Walter (2002) created a 49-item survey entitled the Positive Aspects and Motivation Survey and used it in a three-state study (Indiana, Illinois and Texas) that found increasing job satisfaction. Padalino (2009) used the same instrument and found increasing superintendent job satisfaction in New York State. The Padalino (2009) study, with a 75% superintendent job satisfaction rating, served as the baseline for this study. In this study, superintendent job satisfaction was only measured at 60%. This is a 15% decrease in 6 years. This study used the 49-item survey and added five new questions related to current issues confronting New York State superintendents. These questions asked superintendents their feelings toward: working with the Board of Education, the property tax levy cap, the Gap Elimination Adjustment, the rollout of the Common Core standards, and the new Annual Professional Performance Review. Working with the board of education was strongly positive while the other four were viewed as strongly negative. However, only working with the board of education had a significant correlation to superintendent job satisfaction. Approximately 81% of respondents had positive feelings about working with the board of education. Almost exactly the same 81% of respondents said yes they would aspire to the superintendency if starting their careers over. Thus, superintendent-board of education relations were far more important to superintendent job satisfaction than any external factors measured in this study. Suggested Keywords: superintendent, job satisfaction, school district leadership, superintendent-school board relations, superintendent motivation. [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.]