The overall purpose of this study was to examine the impact of psychological well-being on mental health and behavioral outcomes among transitioning homeless youth in a New York City shelter. The main objective was to elucidate the relationship between psychological health, distress, and behavioral program outcomes. Participants were 116 formerly homeless young adults enrolled in the transitional living Rights of Passage program at Covenant House New York; a homeless youth shelter providing both crisis services and residential transitional living programs to young adults age 18 – 21. The correlates of psychological distress and program outcome were studied in relation to psychological well-being as measured by the Scales of Psychological Well-Being (SPWB) identifying 6 core components of positive psychological functioning including Autonomy, Environmental Mastery, Positive Relationships with Others, Personal Growth, Purpose in Life, and Self-Acceptance. Markers of psychological distress were measured by using the PHQ-9 (Depression), GAD-7 (Generalized Anxiety), PTSD Checklist - Civilian Version (Posttraumatic Stress Disorder), GHQ-12 (General Distress), while behavioral outcome data (i.e., behavioral infractions/disciplinary incidents, employment, discharge disposition, education advancement, and total savings) were assessed via the Efforts to Outcome (ETO) online software database maintained by Covenant House New York. Results of Pearson r correlations demonstrated a statistically significant relationship between psychological well-being and psychopathology. Stepwise regression analyses also showed that certain components of psychological well-being accounted for a significant portion of the variance over time in anxiety, PTSD, and general distress above and beyond initial levels of psychopathology. Additionally, Pearson r correlations and ANOVA analyses demonstrated significant associations with psychological well-being and program outcome including behavioral infractions (verbal conflicts, and non-compliance infractions), time unemployed, total savings, and G.E.D. obtainment. In contrast, psychopathology demonstrated significant associations with only behavioral infractions (verbal conflicts) and total savings. Findings suggest that psychological well-being is differentially associated with program outcome from psychopathology and that interventions aimed at homeless youth may benefit from incorporation of strengths-based, positive psychological approaches.