The purpose of the current study was to explore whether selfcompassion predicted psychological distress over and above childhood maltreatment and attachment orientation in high-risk youths. Fifty-one youths (31 males, 20 females) aged 17 to 24, recruited from a community non-profit organization in St. John's, Newfoundland and Labrador, Canada, were administered validated measures of childhood maltreatment, attachment orientation, self-compassion, and psychological distress. Results indicated that self-compassion was inversely associated with childhood maltreatment, attachment anxiety, attachment avoidance, and psychological distress. However, results did not support the hypothesis that self-compassion was a significant predictor of psychological distress over and above attachment anxiety and childhood maltreatment in high-risk youths. Our results indicated that self-compassion is not well developed in street-involved youths and may be a vital intervention target to heal negative internalized views of the self, while maintaining vigilance to threats inherent in the street environment.