Among people experiencing homelessness, difficulty securing housing is often compounded by concurrent challenges including unemployment, chronic illness, criminal justice involvement, and victimization. The Moving Ahead Program (MAP) is a vocational rehabilitation program that seeks to help adults facing these challenges secure competitive employment. We prospectively studied how MAP graduates (N = 97) changed from the beginning of MAP to about 6 months after graduation. We observed a variety of positive outcomes in not just employment and housing but also health, substance use, and criminal justice involvement. However, these gains were not universal; for instance, participants were less likely to report positive outcomes at follow-up if they started MAP with a serious mental illness, made relatively small gains in work skills, or did not seek mental health treatment during the 6 months after they completed MAP. These findings might encourage program staff to devote additional resources toward supporting at-risk students.