This study aimed to describe the experience of adolescents with Type 2 diabetes and their caregivers during medical encounters, in an effort to improve clinical care and outcomes in this population. Twenty-eight families were recruited from a Midwestern diabetes clinic. Adolescents (13–18 years old) identified as Black (50%), Caucasian (43%), and Hispanic (7%), with variable levels of glycemic control (glycosylated hemoglobin A1c = 5.1–12.9%). Participants completed demographic and disease-related (adherence) questionnaires. Six adolescent and six caregiver focus groups were conducted and transcribed, coded, and systematically analyzed using principles of thematic analysis. Participants reported moderate to high rates of nonadherence. Qualitative themes indicated multiple factors influencing perceptions of the quality of provider–patient interactions. Participants’ experiences of these interactions was affected by provider characteristics (e.g., gender, age), provider approach and communication style, systemic issues (e.g., long wait times), and caregivers assuming primary roles in medical encounters (e.g., more caregiver participation and caregiver disclosure of nonadherence). Focus group discussions provided rich information about the experiences of adolescents with Type 2 diabetes and implicate barriers in provider–patient interactions, including challenges in triadic interactions and communication around nonadherence, suggesting these areas should be considered in efforts to improve provider–patient interactions within this population.