The purpose of this study was to explore the experiences of adolescents with Type 1 Diabetes Mellitus (T1DM) as they transitioned into high school in order to understand the contextual factors that impact diabetic health-related behaviors and self-identity. A qualitative interviewing methodology called consensual qualitative research (CQR) was used. Six high school freshmen with T1DM were interviewed. Adolescents reported both normative as well as diabetes-specific issues (e.g., social challenges of self-care) pertaining to their transition from middle to high school. Implications for school counseling practice are discussed.