Homeless and street-involved youth are considered an extremely high risk group, with many studies highlighting trajectories characterized by abusive, neglectful, and unstable family histories, victimization and criminal involvement while on the streets, high rates of physical and mental illness, and extremely high rates of mortality. While there exists a substantial body of knowledge regarding risk, in recent years attention has been increasingly shifting to the examination of resilience, intervention, and service delivery models for these young people. The present study describes the findings from a quantitative examination of personal and street-related demographics, psychological distress, self-esteem, resilience, and suicidality among 47 homeless and street-involved youth. Key findings indicate that the apparent erosion of mental health variables, including resilience, occurs as a function of how long the youths have been without stable housing. Finally, those youths’ perceived resilience was associated with less suicidal ideation whereas higher psychological distress was associated with higher suicidal ideation, even when accounting for resiliency.