Using dyadic youth-adult interviews, the current study explored characteristics, benefits, and challenges of supportive youth-adult relationships for youths living in neighborhoods with high levels of community violence. Thirty-two dyads of youths between the ages 13 to 21 years (63% female, 88% Black) and their self-identified key adult supports in Pittsburgh, PA, completed semi-structured interviews exploring important qualities of youth-adult relationships, aspects which strengthen these relationships, relationship challenges, and intergenerational support. Data were analyzed using thematic content analysis and an iterative coding process to identify key themes. For youths and adults, important qualities that constituted supportive relationships included being dependable, nonjudgmental, a best friend, and providing unwavering support. Occasionally, youths and adults found it difficult to communicate and understand each other. Despite these challenges, the intergenerational transfer of knowledge and dynamic, bidirectional support were instrumental in helping youths navigate obstacles and thrive. The study highlighted the importance of youth-adult relationships across family and community contexts in empowering youths in neighborhoods impacted by community violence. Dyadic and network-based interventions should be developed that uplift the strengths of youths and their adult supports while simultaneously being attuned to challenges that minoritized youths and adults encounter in neighborhoods impacted by violence.