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 to secure competitive employment. We prospectively studied how MAP graduates (N = 97) changed from the beginning of MAP to about six months after graduation. We observed a variety of positive outcomes not just in employment and housing but also in 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 six months after they completed MAP. These findings might encourage program staff to devote additional resources toward supporting at-risk students.