This article presents findings from a cross-sectional, qualitative, descriptive study, grounded in the positive youth development approach and the Youth Program Quality Assessment model, to examine the effectiveness of specialized settings designed to serve runaway and homeless youth (RHY). From a larger sample of 29 RHY-specific settings across New York State, youth ages 16 to 21 (n=37) from 11 settings were purposively sampled for semi-structured in-depth interviews on their transitions into homelessness, experiences in RHY-settings, and unmet needs. The findings show the population-tailored approaches of RHY-specific settings are vital to engaging and serving RHY due to this uniquely challenged population that is often distrustful of service settings and professional adults and skilled at surviving independently. Four major themes regarding the positive effects of RHY settings emerged: 1) engaging with an RHY setting was emotionally challenging and frightening for youth, and thus the experiences of safety and services tailored to RHY needs were critical; 2) instrumental support from staff was vital and most effective when received in a context of emotional support; 3) RHY were skilled at survival on the streets, but benefited from socialization into more traditional systems to foster future independent living; and 4) follow-through and aftercare were needed as youth transitioned out of services. With respect to gaps in settings, the RHY participants discussed their desire for more balance between needing structure and wanting autonomy and the lack of RHY input into program governance. This study advances the understanding of RHY, their service needs, and the ways settings meet these needs.