This cross-sectional study sought to determine factors associated with sterilization among HIV-positive US women. HIV-positive women aged 18–45 completed an Audio Computer Assisted Self Interview (ACASI) questionnaire. Chi-square tests and multivariable logistic regression evaluated factors associated with sterilization. The median age of the 187 participants was 37, the majority had at least a high school education, and 88% were African American. Nearly a quarter (22%) of women had undergone sterilization at an average age of 25; of these women, 71% cited their HIV-positive status as an important factor in deciding to have a tubal ligation, 22% expressed desire for future children, 32% reported sterilization regret, and 20% reported feeling pressure to undergo sterilization. In multivariable analysis, factors significantly associated with sterilization included non-African American race, no desire for future pregnancy, having heard of any birth control methods making it harder to get pregnant in the future, belief that women should take a break from hormonal methods every few years, and having had a child born with HIV. While almost a quarter of this HIV-positive group was sterilized, many during the height of the early HIV epidemic, a large proportion of sterilized women expressed sterilization regret. Counseling messages for sterilized HIV-positive women should be sensitive to the fact that women may have regret regarding a decision that, in some cases, may historically have been part of provider recommendations to prevent vertical transmission of HIV. Improved knowledge about contraceptive options such as the IUD and implant is needed among HIV-positive women.