The evolution of school finance has become increasingly more complex, and accountability and transparency of spending decisions toward academic outcomes have increased, leading to more demands on the superintendent (Bjork & Kowalski, 2005; Kowalski, 2013; Ramirez, 2013). This has led to evolution of the role of the superintendent position in school districts (Bjork & Kowalski, 2005; Callahan, 1966; Carter & Cunningham, 1997; Decman et al., 2018; Glass et al., 2000; Tienken, 2021). Prior to the educational crisis caused by the COVID-19 global pandemic, Roza (2018) emphasized building fiscal knowledge for educational leaders is important. However, due to the COVID-19 global pandemic's negative effects on education, the federal government has released unprecedented funds known as The Elementary and Secondary School Emergency Relief Fund (ESSER). Roza and Hess (2021) asserted leaders who are better equipped to maximize resources from the federal relief efforts will seize the opportunity, and leaders lacking the fiscal knowledge may have a missed opportunity with detrimental effects on the economy and student outcomes that will be publicly transparent Hess (2021). The purpose of this quantitative correlational study was to explore the relationship between the self-perceived fiscal literacy of New York State school district superintendents, the actions superintendents can take to acquire fiscal knowledge, and their self-perceived ability to maximize ESSER. This study's theoretical framework used Waters and Marzano's (2006) working paper, "School District Leadership That Works: The Effect of Superintendent Leadership on Student Achievement." Several key findings emerged: on average, (a) superintendents had the highest level of agreement regarding their confidence in communicating the budget to stakeholders, (b) informal mentoring with other superintendents helped build fiscal knowledge, and (c) having district goals agreed upon for ESSER spending that included academics and instruction. On average, the lowest level of agreement was their self-perception regarding their district-level administrative advance certificate program, which helped prepare them to make financial decisions. Differences did exist between male and female superintendents' responses to four statements about financial oversight and between superintendents with 1±3 years of experience in any district and any other experience group. Furthermore, the statement regarding their advanced certificate program had the most frequent statistically significant relationships with financial oversight statements despite having the lowest average agreement; informal mentoring had zero statistically significant relationships despite having one of the highest average agreement levels. Finally, the source of their fiscal knowledge had statistically significant relationships with all 13 financial oversight statements. [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.]