With the advent of more advanced treatments and therapies, people with HIV/AIDS are experiencing significant improvements in their health, making many of their ongoing employment and career goals more realistic. However, people with HIV/AIDS continue to have major concerns regarding the impact of working on their benefits and entitlements, including apprehensions about potential economic hardships related to loss of financial supports and health insurance coverage. This article focuses on factors related to employment status, sources of health benefits, and entitlements among people with HIV/AIDS. In addition, results of the study demonstrate differences in employment status, benefit types, and the amount of financial support individuals receive based on gender.