The aim of this study was to examine if the quality of teacher-child interactions and preschool teachers’ occupational well-being (stress and recovery from work) differ depending on contextual factors, i.e., location of the preschool group (daycare center or school), group size and teacher’s work experience. Moreover, it was investigated if teachers’ recovery from work moderates the associations between the stress teachers experience and the quality of teacher-child interactions during the preschool year. Preschool teachers (N = 47) participated in the study in autumn and in spring. The quality of teacher-child interactions in the classrooms was assessed with the Classroom Assessment Scoring System (CLASS Pre-K) on three dimensions: emotional support, classroom organization and instructional support. Moreover, teachers reported their occupational well-being on questionnaires. The results showed that teachers’ occupational well-being and the overall quality of teacher-child interactions did not differ depending on the contextual factors although some differences were found in the quality of teacher-child interactions. Furthermore, recovery from work moderated the associations between teachers’ stress and quality of teacher-child interactions in the classroom indicating that recovery from work is central to teachers’ well-being and interaction quality. Findings are useful for teachers’ preservice and in-service training to enhance the quality of teacher-child interactions and to support teachers’ occupational well-being.