Youth with complex needs in the child welfare population are at increased risk of many negative life outcomes. A large body of research documents the factors that contribute to these difficulties. However, few studies have investigated the factors that facilitate positive outcomes for vulnerable youth. The present study provides some answers by investigating the strength of youth’s connections with caring adults as a significant mediator of the association between perceived emotional social support and personal well-being in a sample of 25 youth with complex needs in care. The results show that strong connections with caring adults mediates the association between perceived emotional social support and personal well-being. Implications for professionals, service providers, and larger systems are discussed. The findings of this study offer hope for youth in care at risk of poor outcomes, as strong relationships with caring adults can make a significant difference in their lives.