Building upon contemporary models of teaching that suggest that teachers’ own well-being is related to their classroom practice and student outcomes, we examined whether middle school teachers’ mindfulness skills were related to their concurrent occupational health and well-being (job stress, occupational burnout, and depressive and anxiety symptoms), and quality of their interactions with students in their “most stressful” class during the school day. Multivariate regression analyses of 58 middle school teachers indicated that teacher mindfulness was significantly associated with lower levels of job stress, occupational burnout, and depressive and anxiety symptoms; and higher levels of observers’ ratings of teachers’ emotionally supportive interactions with students in their most stressful classroom. Occupational burnout, in contrast, was negatively related to observers’ ratings of emotional support and organization in the classroom. Results suggest individual differences in middle school teachers’ mindfulness may affect their interactions with students in the middle school classroom directly and through reductions in burnout, though longitudinal studies of these relations are needed. Findings are discussed in relation to intervention efforts to improve teacher mindfulness through training in order to support occupational health and well-being, improve the quality of teacher-student interactions in the classroom, and increase student engagement and learning.