Introduction: In the later years of medical school, medical students learn through clinical rotations at medical institutions. Using cognitive apprenticeships as the theoretical reference for teaching strategies, this study aimed to assess how clinical teaching strategies benefit medical students' wellbeing in the workplace.Methods: Our target population comprised two cohorts of medical students in the seventh year of a 7-year medical education program in Taiwan, undergoing clinical training at a tertiary medical center between August 2012 and May 2014. After informed consent was obtained, participants were regularly mailed a validated, structured, and self-administered questionnaire to evaluate their clinical teachers' teaching strategies and their personal wellbeing at the end of individual specialty rotations, and medical students' were freely permitted to respond to each invitation. Eighty-seven medical students returned 1364 responses, which were included in the structural equation modeling.Results: We determined that the Inspiring teaching strategy, characterized by articulation, reflection, and exploration, was related to reduced burnout among medical students and an increased sense of compassion satisfaction; the Directing teaching strategy, characterized by modeling, coaching, and scaffolding, was related only to reduced burnout among medical students but not to compassion satisfaction during the clinical training.Conclusions: Clinical teaching strategies were demonstrated to affect, to various extents, medical students' wellbeing with respect to factors such as burnout and compassion satisfaction in the workplace. Clinical teachers and educators should increase efforts to develop Inspiring teaching skills to shift the balance of responsibility and to support students in the teaching and learning relationship.