Resilience, the ability to bounce back in the face of adversity or trauma, plays a crucial role in street-involved youth’s (SIY) capacity to overcome risks. Social connectedness and self-esteem have been identified as possible protective factors in the lives of SIY. A secondary analysis of 155 SIY was conducted to explore the relationship between social connectedness and self-esteem with resilience. Correlations of study variables with demographic characteristics and mental health descriptors were also examined. Results indicate that resilience is positively and significantly correlated with social connectedness and self-esteem. Additionally, those with higher levels of resilience, social connectedness and self-esteem had lower levels of depression, hopelessness, suicidality and substance misuse. Enhancing social connectedness and self-esteem may strengthen resilience, enabling youth to move forward despite the deleterious conditions associated with homelessness.