This chapter focuses on the Homeless Prenatal Program in San Francisco dedicated to working with pregnant women who are homeless. It has received three grants from the Foundation since 1992. The author discusses the chief instigator behind the program, Martha Ryan, executive director and founder, who recognized that pregnancy could be a window of opportunity for a homeless woman—a turning point focused on the new responsibilities of motherhood. The Homeless Prenatal Program was one of a very few that were given two Local Initiative Funding Partners awards; the first for its work with homeless pregnant women and the second for providing services to women leaving prison. The author documents the growth and development of the program. He concludes by raising the important question of whether a local program, such as this one, can be replicated successfully in other parts of the country.