As the COVID-19 pandemic shook the very foundation of our educational systems, Connecticut created adjustments through the 2020-2021 Teacher Evaluation Flexibility Plan. Using a qualitative phenomenological research design, three research questions were explored through the theoretical lenses of Knowles' (1978) adult learning theory and Weick's (1995) sensemaking theory. This study explored the lived experiences of Connecticut high school principals as they made sense of and implemented the adjusted plan during the 2020-2021 school year in order to fill a gap in the educational research surrounding principals' perceptions of implementing teacher evaluation during the COVID-19 pandemic. Results showed four key themes and two subthemes which, when synthesized, formed an essence of the experience for participants. This essence reflected the importance of support, the use of technology, previous pedagogy, the strain of the pandemic, reliance on previously established systems, and the responsibility of capacity building in relation to school climate. The results of this study provide context for state policy makers, higher education institutions who provide programing for aspiring administrators, and central office administrators charged with supporting building administrators. As the impacts of the COVID-19 pandemic may be felt for many years, it is imperative we continue to learn from these experiences to support future educational leaders as they prepare to lead our post-pandemic schools. [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.]