Aside from the personal and health difficulties brought about by the COVID-19 pandemic, teachers also faced tremendous work-related challenges that led to increased stress levels and poorer well-being. This is especially true for resource-constrained schools in an Eastern context. The present study aimed to examine the moderating role of principal autonomy-support on the relationship between stress and teacher well-being during the early stages of the pandemic. Data was collected from 1150 K-12 teachers in the Philippines and hierarchical multiple regression was used to assess the moderating effect of principal autonomy-support on the relationship between stress and well-being. Findings show that stress was negatively associated with emotional, psychological, and social well-being and principal autonomy-support moderated the link between stress and psychological well-being. Johnson-Neyman plots and simple slopes analyses demonstrated that the negative relationship between stress and psychological well-being is more pronounced for teachers who reported lower autonomy-support from principals and weaker for those who reported higher principal autonomy-support. The study highlights the crucial role of autonomy-supportive school leadership in mitigating the adverse effects of stress on teachers' well-being, particularly in the challenging backdrop of a pandemic. The findings further corroborate the relevance of autonomy-support on well-being not only in the Western perspective but specifically within an Eastern, lower-middle-income context. Key discussions and research implications for improving teacher well-being are discussed.