In this qualitative grounded theory study, I interviewed participants from and analyzed documents associated with three community/state colleges in Florida. Additionally, I have included the perspective of key informants from the state and/or the Florida College System. The purpose of this qualitative grounded theory study was to develop a substantive theory to explain the process by which senior administrative leaders engaged in fiscal decision-making due to shifting funding sources during the COVID-19 pandemic. Although prior decision-making theories exist, such as rational choice theory and garbage can theory, these theories do not address how fiscal decisions are made in higher education institutions during times of extended crisis exemplified by the COVID-19 pandemic. This research study found that during the COVID-19 pandemic leaders sought to establish resilience as part of their fiscal decision-making process to ensure their ability to lead and maintain viable institutions of higher education. Moreover, through the fiscal decision-making process, the leaders in this study did not permit themselves or their institutions to accept the status quo, rather they extended themselves and their organizations to stretch beyond prior capabilities to respond to ever changing needs of students as well as external stakeholders brought about from the COVID-19 pandemic. The collective experiences of these leaders during the COVID-19 pandemic resulted in the resilient stretching theory of community college fiscal decision-making, which will be further expounded upon throughout this research study. [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.]