With the introduction of combination antiretroviral therapy (ART) worldwide, youth with perinatal HIV infection are increasingly surviving childhood and transitioning to adult care. Although a normal life span is anticipated posttransition, successful transition to adult HIV care has proven difficult, with worse outcomes posttransition than in pediatric and adult care. This study is a qualitative analysis of data from 4 focus groups of pre- and posttransition patients, caregivers, and healthcare providers in the Dominican Republic at an institution that provides comprehensive treatment including ART for HIV-infected persons of all ages. All groups discussed the problems and challenges that patients, caregivers, and providers experience while living the transition process and beyond. Five major themes emerged: the trauma of transition itself, ART adherence, experience and impact of stigma, social supports and barriers, and recommendations for improving outcomes. Participants' insights offered approaches for a versatile structured transition process.