In the past 30 years, the U.S. Department of Housing and Urban Development (HUD) has increasingly focused on promoting the self-sufficiency of housing assistance recipients through initiatives such as Jobs Plus, Family Self-Sufficiency (FSS), and the Rent Reform Demonstration. This paper synthesizes the evaluations of these programs to provide insight into short-, medium-, and long-term successes and limitations of these programs. It examines plausible reasons for their limited success. The paper then describes potential pathways forward.