Community-based service providers often hire youth living with HIV (YLH) as peer leaders for delivering HIV education to uninfected adolescents. Life narratives were collected from 44 YLH during a hypotheses-generating two-year ethnographic study. About 30% of the youth were employed as peer educators. While 60% of the 44 youth had a lower-class background, only 23% of the peer leaders were lower class. One-fifth of the sample were female, but more than one-half of the peer leaders were female. After identifying and categorizing difficulties experienced by the peer leaders, a frequency count of each theme was conducted. Issues about professional boundaries were evident in 38.5% of the youth's narratives, indicating conflicts in their roles as peer leaders; 23% of the youth engaged in substance use and sexual behaviors that placed themselves and uninfected youth in their peer educator programs at risk; and 8% of the youth reported relapse while peer leaders. The observations suggest reconsideration or restructuring of existing peer-education models that employ YLH.