Adolescents are in a dynamic period of cognitive, emotional, and behavioral development. School-based interventions that focus on social-emotional learning, including the development of self-regulation skills, have been shown to have positive impacts on students' mental health and academic achievement. In this qualitative study, we examine health education teachers' and school counselors' views of their students' challenges and their strategies for supporting students' social and emotional development. We conducted 16 focus groups and interviews with 24 educators: 16 middle level health education teachers and eight school counselors. Our qualitative analysis of the transcripts indicated that both teachers and counselors described the contexts for students' challenges as related to academic/school pressures, social media, peer relationships, and home influences. Educators also identified students' challenges as being related to their developmental stage, challenges with impulsive behaviors, and difficulty regulating emotions. Strategies for supporting students' self-regulation included day-to-day interactions, skills instruction and practice, positive teacher-student relationships, and a structured classroom environment. Implications for professional development for middle level educators and the implementation of preventive interventions are discussed. [For the Grantee Submission, see ED628940.]