We explore how a group of service-providing organizations have strategically engaged in actions to cultivate legitimacy among varied external stakeholders. Using the case of syringe service programs, programs that use harm reduction services to engage the population of drug users, the authors use qualitative methods to examine how these stigmatized yet increasingly accepted organizations have sought to cultivate legitimacy among the audiences that dictate the means of their survival. Findings show that SSPs use different strategies to maintain and foster legitimacy depending on how long they have existed, organizational sector, relationships with stakeholders, and the drug use stigma in their immediate community. This article can inform how human services organizations can use different stigma-lessening strategies to cultivate organizational legitimacy among the external audiences on which they are dependent.