Ongoing discourse in education emphasizes the need for schools to adapt to 21st-century teaching methods to adequately prepare students for the future society and workforce. The problem is that schools battle constraints of priorities and limited resources, and the onset of the worldwide COVID-19 pandemic has only further unearthed and magnified educational inequities, outdated practices, and a myriad of inconsistencies in addressing the needs of students. The purpose of this qualitative explanatory case study was to explore how a highly ranked middle school has and is fostering 21st-century learning, what challenges they have experienced in this process, and how the prioritization and implementation of 21st-century skills have been impacted since the onset of the COVID-19 pandemic. Drawing on activity theory and 21st-century teaching and learning frameworks, the study involved interviews and observations of 15 experienced educators, as well as document analysis of the school's program of studies and reflective journaling. Findings revealed a clear consensus on the necessity of transitioning to 21st-century teaching and learning to adequately equip students for the future. However, educators faced obstacles in establishing a shared understanding, balancing competing priorities, and harnessing the potential of educational changes brought about by the COVID-19 pandemic. The study's results provide actionable insights for schools seeking to embrace 21st-century teaching and learning, promising practical advice and direction in this pursuit. [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.]