Exiting prostitution is an often complicated, arduous process. Many barriers constrain women’s movement out of prostitution. Factors such as stigma are rarely examined. Utilizing a case study approach, semistructured interviews were conducted with 14 SEPP prostitution court participants and eight professionals working with participants, to understand the ways in which stigma affected the exiting process among women with extensive histories of prostitution. Rigorous qualitative analysis revealed three types of stigma: structural stigma, public stigma, and self-stigma. Failing to address stigma can thwart the efforts of prostitution courts and social service program trying to help women exit prostitution.