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This paper examines the mentor-coach role as a supportive structure for experienced teachers’ increased well-being. It reports on a qualitative case study (Yin, 2014) of one Canadian school district that abductively analysed (Tavory and Timmermans, 2014) data collected from surveys, interviews, focus groups, and documentation with and against Seligman’s (2011) well-being theory. All five PERMA elements emerged related to positive emotion, engagement, (positive) relationships, meaning, and accomplishment. However, the mentor-coach role is not a panacea for educator well-being. Rather, study findings indicated that the quality and effectiveness of the mentoring and coaching relationship is critical and negative experiences—if left unattended—can also contribute to mentor-coach stress and increased workload.