Finding work and/or re-entering the workforce can be extremely challenging for persons living with HIV/AIDS. Also difficult is assisting them in the process, mostly because there is little documentation or resources about programs that provide vocational services specifically for this population. In response to this dilemma and because it was perceived as a win/win situation, three urban residential community organizations serving the HIV/AIDS population, decided independently to create in-house work opportunities for their clients. All of these organizations are a variation of the same theme: transitional/supportive housing for persons with HIV/AIDS that were formerly homeless and are now interested in becoming increasingly self-sufficient. This article will present a program description that addresses unique manner in which these three sites created in-house job programs in the areas of receptionist, kitchen, and maintenance work. More specifically, this paper will address the strengths, limitations, and ethical considerations that guided program development.