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Teaching through a pandemic, political ire directed at teachers, and moral panics playing out in school board meetings have hurt the teaching profession and impacted the mental health and well-being of teachers. These challenges have increased the need for school leadership to focus on teachers’ mental health and well-being. Two pathways to explore teacher well-being is through fostering flourishing and a sense of belonging. We use a three-tier educational data science approach to explore interviews that we conducted with 39 teachers in their first five years in one school district to explore how they experienced sense of belonging and flourishing in their schools. We detail our findings in the below.