In an effort to investigate school administrator self-efficacy during the COVID-19 pandemic, two public high school administrators from the same high school in a Southeastern U.S. state were interviewed virtually two times a week during the first six weeks of the 2020-2021 school year. Selection of participants was accomplished using convenience sampling, as both persons completed a principal preparation program where the lead researcher served as an instructor. The participants were surveyed before and after the study using questions from the Principal Self-Efficacy Survey (PSES) as well as researcher-developed questions specifically related to work life during the pandemic. The study revealed the degree that these administrators defined their work experiences during this period, based on four distinct perspectives, including: (a) structural, (b) symbolic, (c) political, and (d) human resources. Also, the study revealed administrator perceptions of equity and access among various constituents at their school, including teachers, support staff, students, parents, and members of the broader school community. Using open systems theory as a theoretical perspective, the study revealed six emergent themes that related to their work while opening school during a world crisis: (a) technology access/instruction, (b) informational/procedural ambiguity, (c) resource dependency, (d) policy adaptability, (e) stakeholder disposition, and (f) methods of communication. Focused on a principal and assistant principal at a single high school, this case-study illuminates the personal and professional challenges faced by these administrators during the COVID-19 pandemic.