The increased life expectancy of perinatally HIV-infected adolescents necessitates the transition from pediatric to adult infectious disease care. Significant differences exist between pediatric and adult HIV clinic models, and adequate preparation is critical for successful transition. The expectations of youth on the cusp of this transition and their guardians have not previously been explored. Semistructured interviews were conducted with 40 perinatally infected adolescents (mean age, 17.3 years; 90% African American; 57.5% female; 57.5% in high school) currently receiving care in a pediatric infectious disease clinic in the southeast United States and 17 guardians about their expectations related to the pending transition to adult care. Interviews were transcribed and coded for emergent themes. Many adolescents had difficulty articulating expectations of their transition to an adult clinic, reporting they did not know what to expect. Others looked forward to increased responsibility and control, while some expressed concerns over leaving their current providers and having to establish new relationships. Most guardians viewed the transition to adult care as a tool to facilitate maturity. Several indicated they had not discussed transition with their child and were waiting for their child to initiate a conversation about it. Given the importance providers place on preparing youth for transition, it is surprising that many adolescents had no expectations about this impending change. This indicates a need for improved communication between providers and adolescents to enhance preparation and ultimately transition success. Additionally, guardians play an important role in the transition process and may need support to discuss this process with their child.