The global COVID-19 pandemic has resulted in a rapid transition to online teaching for universities during the current and ensuing years. Graduate social work students need advanced knowledge and skills in leadership and supervision to become future leaders in human service organizations. However, social workers are often promoted to management from direct service positions without adequate skills and training and schools of social work may not formally educate students for leadership and administrative positions. Scholarly literature and research about leadership training for social work students, specifically online training, is also scarce. This article examines how two Canadian schools of social work addressed this gap through the development of graduate master of social work courses on leadership and supervision as mandatory components of their curriculum, through on-campus and online formats. Varying course approaches, topics, instructional strategies, assignments, and themes collected and analyzed from online surveys of student feedback are described, emphasizing strengths (satisfaction, relevance, benefits, course design), challenges (content, timing), and lessons learned (importance, new learning, confidence, future roles). Recommendations for similar educational disruptions, future courses, and practice implications, including teaching resources and instructor adaptability to support the rapid transition to online and blended learning formats, are also discussed.