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While many teachers have reported increased stress and worry about the future as the result of COVID-19, some have demonstrated great resiliency. This mixed-methods study explored teacher well-being and stress during COVID-19. Preliminary findings suggest that younger teachers reported lower levels of well-being compared to more seasoned colleagues and teachers with the lowest level of confidence using educational technology reported the highest levels of stress. Preliminary findings also suggest that teachers felt a “blurring of boundaries” intensified feelings of stress, particularly as they faced multiple demands with limited support. However, efforts to foster school connectedness, find a sense of meaning in their work, and transparent and empathetic leadership bolstered positive feelings and well-being. Implications for practice are discussed.