This study examined parental and caregiver distress among families caring for children with type 1 diabetes as the child transitions into Emerging Adulthood. More than 96 hours of semistructured interviews were conducted with 19 adult caregivers including parents, grandparents, and other adult family members of 10 children. Each research partner participated in multiple face-to-face, 1- to 1.5-hour long-evolving interviews over the course of 4.5 years. Paradoxically, caregivers were found to experience significant increase in distress as their child with diabetes entered the developmental stage of Emerging Adulthood, 18 to 25 years old, by which time they should be masters of self-care, and parental distress should begin to decline. This increase in familial distress was associated with the emerging adults leaving the home, being unable to maintain an acceptable level of self-care, and experiencing declining health, frequent visits to the emergency department, and repeated hospitalizations. These findings suggest that parental distress from caring for a child with diabetes continues as the child ages, matures, and transitions into adulthood and may be exacerbated when the emerging adult with type 1 diabetes leaves the home and the direct observation and care of the parent.