Much has been written since the first appearance of HIV/AIDS in 1981 about its effects on the Canadian health care and social services systems. However, researchers have given limited attention to issues of entry or re-entry to the competitive job market for HIV positive individuals. The emergence of highly active antiretroviral therapies (HAART) has allowed a significant number of persons who are HIV positive to experience a major recovery in health and energy. This increase in physical health has in turn led to a re-examination of the possibility of returning to former types and levels of activity, including the prospect of going back to work or entering the competitive workforce for the first time. The purpose of this paper is to outline some of the issues and concerns that impact HIV positive individuals' attempts to return to or enter the competitive workforce, particularly those relating to disability policies and public insurance. Data from in-depth interviews with a sample of people living with HIV/AIDS (PHAs) are used to help illustrate the disconnect between these policies and the lived experiences of PHAs. Also discussed are the opportunities for Canadian policies and practices to employ a functional definition of disability and a philosophy of early intervention in vocational rehabilitation.