The coronavirus disease 2019 (COVID-19) pandemic has altered approaches to anesthesiology education by shifting educational paradigms. This vision article discusses pre-COVID-19 educational methodologies and best evidence, adaptations required under COVID-19, and evidence for these modifications, and suggests future directions for anesthesiology education. Learning management systems provide structure to online learning. They have been increasingly utilized to improve access to didactic materials asynchronously. Despite some historic reservations, the pandemic has necessitated a rapid uptake across programs. Commercially available systems offer a wide range of peer-reviewed curricular options. The flipped classroom promotes learning foundational knowledge before teaching sessions with a focus on application during structured didactics. There is growing evidence that this approach is preferred by learners and may increase knowledge gain. The flipped classroom works well with learning management systems to disseminate focused preclass work. Care must be taken to keep virtual sessions interactive. Simulation, already used in anesthesiology, has been critical in preparation for the care of COVID-19 patients. Multidisciplinary, in situ simulations allow for rapid dissemination of new team workflows. Physical distancing and reduced availability of providers have required more sessions. Early pandemic decreases in operating volumes have allowed for this; future planning will have to incorporate smaller groups, sanitizing of equipment, and attention to use of personal protective equipment. Effective technical skills training requires instruction to mastery levels, use of deliberate practice, and high-quality feedback. Reduced sizes of skill-training workshops and approaches for feedback that are not in-person will be required. Mock oral and objective structured clinical examination (OSCE) allow for training and assessment of competencies often not addressed otherwise. They provide formative and summative data and objective measurements of Accreditation Council for Graduate Medical Education (ACGME) milestones. They also allow for preparation for the American Board of Anesthesiology (ABA) APPLIED examination. Adaptations to teleconferencing or videoconferencing can allow for continued use. Benefits of teaching in this new era include enhanced availability of asynchronous learning and opportunities to apply universal, expert-driven curricula. Burdens include decreased social interactions and potential need for an increased amount of smaller, live sessions. Acquiring learning management systems and holding more frequent simulation and skills sessions with fewer learners may increase cost. With the increasing dependency on multimedia and technology support for teaching and learning, one important focus of educational research is on the development and evaluation of strategies that reduce extraneous processing and manage essential and generative processing in virtual learning environments. Collaboration to identify and implement best practices has the potential to improve education for all learners.