This mixed methods case study examined teachers' levels of compassion satisfaction and compassion fatigue, or the combination of burnout and secondary traumatic stress, and strove to understand how teachers experience these phenomena and what supports could be used to alleviate some of the harmful symptoms of compassion fatigue. For this study, I used a healing centered approach and the Compassion Fatigue Theoretical Model, after reviewing previous literature around compassion fatigue and satisfaction, workplace well-being, school well-being, and context specific efforts in the District of Columbia Public Schools system that involved teacher and staff well-being. The final research design produced findings around the importance of qualitative research in understanding well-being and compassion fatigue and satisfaction, suggestions for schools and districts to support teacher well-being, and the effect the pandemic has had, directly on teachers and indirectly through the pandemic's effects on their students.