This research explores the perceptions of adolescents and young adults (AYA) living with perinatally acquired HIV (PHIV) as they transition into parenthood. We conducted hour-long, semistructured audio-recorded interviews with a purposive sample of 17 AYA parents with PHIV who were current or former patients at two US pediatric/adolescent infectious diseases clinics. Participants were asked about challenges/rewards of parenting and anticipated future fertility desires/intentions. Analysis of the transcribed interviews was guided by grounded theory. Mean age of participants was 22 years. The majority were African American (n = 8) or Hispanic (n = 6) and female (n = 14). Two participants were pregnant and others had a range of 1-3 children (mean = 1.4), one of whom was HIV positive. Analyses revealed that time with their child was a valuable commodity. Participants expressed concerns about not “being there” for their child due to sickness and worries that their child may experience HIV-related discrimination once a parent's HIV status was disclosed. The importance of being a role model and present in their child's life over time was emphasized and served as motivation to pursue education and employment opportunities. Those parents who intended to have another child were motivated by a strong desire to create a legacy and a family of their own as a way to deal with HIV-related losses and stigma. Participants reported the importance of emotional support offered by providers, as well as concrete social services available in that care setting even if they had transitioned to adult care. AYA also expressed parenting rewards/challenges similar to those of their uninfected peers. As youth with PHIV continue to mature, increasing numbers will become parents. It is incumbent upon both pediatric and adult providers to support newly formed families living in the context of intergenerational HIV infection.