Using the nationally representative Head Start Family and Child Experiences Survey 2014 (FACES 2014), this study examined the associations of Head Start children’s behavioral challenges with teachers’ well-being (i.e., depressive symptoms, job commitment) and intent to leave, controlling for teacher characteristics. We sought to explore the direct and indirect associations of Head Start children’s behavioral challenges with teachers’ intent to leave, potentially mediated by teacher well-being. The results indicate that children’s behavioral challenges were not directly associated with Head Start teachers’ intent to leave. However, these behavioral challenges were indirectly associated with teachers’ intent to leave through their link to teachers’ depressive symptoms and commitment. This study provides insight for policy and practice as the field aims to build a healthy and sustainable workforce committed to a high-quality early care and education experience critical to children’s development. (author abstract)