This study examined factors associated with contemplating returning to work among unemployed persons living with HIV/AIDS (PLHA) in a large urban city in the United States. A mailed, self-administered survey gathered information from 757 unemployed PLHA. Chi-square and logistic regression analyses were used to determine associations between contemplating returning to work and sociodemographic characteristics, health factors and perceived barriers to employment. We found that most unemployed PLHA (74%) were thinking of returning to work, but perceived significant barriers such as loss of disability income benefits (73%), loss of publicly-funded health insurance (67%) and workplace discrimination (66%). Univariate analyses indicated that contemplating returning to work was significantly associated with sociodemographic characteristics, health factors and perceived barriers to employment in the following areas: (1) availability of health insurance, (2) personal health and physical ability, (3) health concerns related to working and the work environment, and (4) current job skills. Multivariate analyses indicated that: gender, age, race/ethnicity, health insurance type, health status and the belief that health will improve if employed were independently associated with contemplating returning to work. In summary, a substantial proportion of unemployed PLHA may contemplate re-entering the workforce. Assistance is needed to help PLHA address perceived barriers that may prevent them from seeking employment.