The management of youth with severe obesity is strongly impacted by social determinants of health and family dynamics. We present case studies of three patients seen in our tertiary care obesity treatment clinic as examples of the challenges faced by these patients and their families, as well as by the medical team. We discuss how these cases illustrate potential barriers to care, the role of child protective services, and we reflect upon lessons learned through the care of these patients. These cases highlight the need for comprehensive care in the management of youth with severe obesity, which can include: visits to multiple medical specialists, and mental and behavioral health providers; school accommodations; linkage to community resources; and, potentially, child protective services involvement. Through the care of these youth, our medical team gained more experience with using anti-obesity medications and meal replacements. The care of these youth also heightened our appreciation for the integral role of mental health services and community-based resources in the management of youth with severe obesity.