Transformative learning theory has been recommended as a pedagogy of uncertainty for accommodating new beliefs that enable humans to thrive amid the challenges and complexity of our world. As higher education institutions embrace new roles and responsibilities, few studies have focused on how the disruptions caused by COVID-19 may facilitate formative learning experiences. This study explored how registrars responded to the challenges facing clinical training during the first wave of COVID-19, and how the impact of these disruptions prompted personal and professional development. Registrars completed an online qualitative SWOT (strengths, weaknesses, opportunities, and threats) analysis of their training experiences during the COVID-19 pandemic. Data were thematically analysed. Four hundred and five responses were received from 54 registrars. Themes related to challenges included mental distress, resource constraints, and compromised and inadequate training. Themes related to strengths and opportunities included new learning experiences, resilience, coping strategies, and enhanced graduate competencies related to leadership, collaboration, communication, and health advocacy. The disruptive and disorienting elements of COVID-19, although situated in chaos, aggravating the constraints of training in under-resourced settings, also provided unexpected learning opportunities. These findings highlight the transformative potential of disrupted learning contexts and the need for responsive curricular to enhance graduate competencies, adaptability, and resilience.