The present study examined the extent to which the association between teacher reports of preschool children’s approaches to learning–the ways in which children engage in learning activities–and children’s academic skills was dependent upon teacher emotional support. Multilevel models were estimated using data from a sample of diverse urban Head Start children (N = 301 children across 53 classrooms). Findings showed direct associations between attention persistence and children’s literacy and mathematics skills, as well as an association between attitude toward learning and literacy skills. Cross-level interactions indicated that higher emotional support strengthened the relationship between attitude toward learning and children’s literacy skills. Our findings suggest when children are enrolled in classrooms characterized by respectful, warm, and supportive teacher-child interactions, there are benefits for children’s approaches to learning and academic skills. Implications for future research, policy, and practice are discussed. (author abstract)