Promoting teachers' well-being through interventions within childcare environments has been associated with children's social-emotional development, teacher behaviors, and job-related factors. The current study aimed to examine whether individual and contextual factors differentially impacted well-being outcomes among teachers who participated in a well-being program. Participants included 505 teachers who were enrolled in the program and completed pre- and post-intervention questionnaires on well-being outcomes (i.e., health motivation, physical activity, job stress, and resilience). Multilevel modeling estimated whether organizational, individual, and intervention-related characteristics were associated with program outcomes. Exploratory analyses examined the interactive effect of Teacher race and teacher–coach racial match over time. Results from the three-level model showed a significant change in study outcomes over time. Additionally, teacher race was associated with health motivation and resilience, such that Black, Indigenous, and people of color (BIPOC) teachers reported greater improvements over time, compared to White teachers. Exploratory analyses showed a significant three-way interaction, which indicated that White teachers who were paired with a Black coach were associated with improvements in health motivation over time. Importantly, baseline differences in health motivation and resilience among BIPOC and White teachers may explain the variance in the significant effects. Findings from the present study have important implications for practitioners disseminating teacher well-being interventions in schools. (author abstract)