Transitional care represents a critical juncture in the continuing care of patients with chronic conditions, particularly for adolescent patients. It also represents a significant point of failure in that process for adolescents, with many patients experiencing difficulties during the transition between adolescent and adult medicine that lead to negative long-term impact on health and wellbeing. This thesis aims at addressing adolescent transitional care processes and its obstacles through a broad medical humanities inquiry in a multidisciplinary dialogue between philosophy, social sciences, and medicine. The social, anthropological, and medical concepts of adolescence and autonomy were derived from a literature review and used to identify and philosophically analyze obstacles to adolescent transitional care. Studies were used to illuminate those obstacles. For a first person-perspective analysis, an autoethnography was developed to provide patient testimony, towards improving the reflection on transitional care. This analysis tested the alignment of the author’s experiences in interacting with a healthcare transition as part of the patient population with those recorded in the literature. This study has found barriers and facilitators concerning autonomy and communication at many levels and among many parties involved in the transition, such as patients, caregivers, healthcare providers, and healthcare systems operations, particularly regarding insurance management. This study recommends a focused coordination of primary care and/or transitional care specialists with the participation of adolescent patients’ voices and testimony to develop and manage challenges to autonomy in transitional care.