This article presents a longitudinal evaluation of the Gateway Transitional Families Program, an innovative self-sufficiency program designed to help public housing residents leave public housing for their own homes. The evaluation followed participants and a comparison group over six years to isolate program impacts on employment and receipt of Aid to Families with Dependent Children (AFDC), food stamps, and housing assistance. Many participants dropped out of the program. Difficulty in juggling educational and child-rearing responsibilities, noncompliance with program or public housing regulations, low wages while in the program, impatience with the length of the program, and staff shortages and turnover contributed to the dropout rate. Those who finished the program experienced modest increases in income, decreases in receipt of AFDC and food stamps, and reduced reliance on housing assistance relative to comparison group members. Furthermore, graduates were more likely than comparison group members to have bought a home.