Recent studies on homeless adolescents suggest that the profiles of homeless adolescents are heterogeneous, and that certain clusters of homeless adolescents demonstrated resiliency and positive coping strategies. This study examined the relationship between HIV-related risk factors and resiliency (survival skills) of homeless adolescents over a 2-year period. Those who did not engage in unprotected sex reported significantly higher survival skills scores. Similarly, those who were monogamous during the study period reported significantly higher survival skills scores. However, there was a significant decline in survival skills scores after 6 months, regardless of the HIV-related risk factors. Findings from this study point to the urgent need to identify and target resilient adolescents early on to provide interventions to facilitate the transition to stable living situations before their resiliency deteriorates.