Youth with chronic developmental delays and comorbid psychological disorders (complex needs) who live in out-of-home care are at increased risk of difficulties in all life areas. Few studies have investigated factors that facilitate positive outcomes. This study investigated the strength of youth’s connections with caring adults as a significant mediator of social support and personal well-being. A convenience sample of 25 youth with a mean age of 18.14 years old who lived in a group home or semi-independent living settings rated their social support (instrumental and emotional), strength of connections, and personal well-being on self-report measures. Research questions were examined with correlation, regression, and mediation analyses. Older youth reported less instrumental social support; this type of support did not correlate with well-being. Emotional support correlated with well-being. Strong relationships with caring adults partially explained how youth who perceive more emotional support feel happier about their life overall. The findings of this study show how to support youth with complex needs in care during the challenge of transitioning to adulthood and provides evidence that allows us to identify the positive impact of perceived strong connections with caring adults. Perceived strength of relationships with caring adults has a great influence on their well-being. HIGHLIGHTS Youth in care with complex needs experience poor outcomes in the transition to adulthood. Perceived instrumental support was negatively correlated with age; older youth in care perceive less instrumental support. Emotional support predicts personal well-being, but instrumental support does not. Strong connections with adults help youth feel happy about their future outcomes.