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Job-related stress is negatively linked with teachers’ physical and mental well-being, contributing to many leaving the profession. This exploratory study fills a gap in the literature to better understand how to progress teachers’ well-being knowledge and practices, which are critical to teacher and student success. We coded teacher reflections from a graduate course on teacher and student well-being to report the Micro-/Macro-/Exo- system influences on their well-being, how teachers’ understandings changed over time, and content that contributed to expanding their knowledge and well-being practices. Findings indicate students, family and friends contributed to teacher well-being, but education-related Macro- and Exo- system influences detracted from well-being. Emotional intelligence, flourishing, and small group sessions with class peers primarily progressed teachers’ understanding and practices.