A growing body of research connects principal leadership to student achievement, but the effects of principal learning in conjunction with leading have not been richly explored. This dissertation provides a different perspective on principal leadership by looking at principals' approaches to their own learning while surviving and sometimes thriving amongst complex, pandemic times. This work explores possible links among learning approaches, decision-making, and problem-solving as leaders. Shining a light on the current principalship, as well as, increasing our understanding of principals' challenges, experiences, perceptions of identity, and approaches to learning may have implications for principals' professional practice and greater support for school leaders. Using a qualitative multi-case study design, I explore and address the following research questions: 1) How are principals learning and leading in the context of COVID-19? a) What learning perspectives do principals intentionally or unintentionally leverage when addressing changes associated with adaptive challenges such as COVID-19? 2) What prior and new learning do principals identify as helpful for understanding and addressing adaptive challenges such as COVID-19 in their school context? a) How do principals learn through grappling with current challenges? b) What and who do principals say they draw on for learning? 3) How did principals view their identities as a support in the COVID-19 context? [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.]