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Teachers’ emotional experiences influence outcomes including stress and burnout, both of which were exacerbated during the COVID-19 pandemic. With this sequential explanatory mixed-methods study, we sought to understand how teacher-level (i.e., emotion regulation strategies) and school/district-level factors (e.g., autonomy supportive leadership) combined to inform various aspects of teachers’ emotional experiences. The structural equation model based on teacher survey data evidenced significant relationships between teachers’ negative emotions, emotion regulation strategies, enthusiasm, feelings of burnout, and perceived autonomy support. Qualitative analysis offers additional insight into the nature of these relationships across school and district contexts. Implications for supporting teacher retention and reducing burnout are discussed.