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Background: Improving HIV detection and prevention remains a critical public health initiative that requires policy-based solutions. This study sought to compare HIV detection/prevention behaviors before and after healthcare reform in Massachusetts, USA, among heterosexually active persons - the group with the highest reported number of undiagnosed HIV cases. The current study sought to (1) characterize differences in insurance coverage and HIV detection/prevention behaviors between cycles 1 (2006) to 5 (2019); (2) evaluate socio-demographic disparities in insurance coverage accounting for cycle; and (3) evaluate associations between health insurance coverage and HIV detection/prevention behaviors accounting for cycle and socio-demographics., Methods: This is a secondary analysis of the National HIV Behavioral Surveillance (NHBS) project: Boston HET cycle (i.e., made up of heterosexually active persons living in the Boston area) data. Descriptive, bivariate (e.g., chi-square), and multiple logistic and negative binomial loglink regression analyses were conducted., Results: In chi-square analyses with post hoc Bonferroni tests, the proportion of participants with current health insurance significantly increased from cycle 1 (77%) to cycle 2 (95%), p < .001. In the regression models that controlled for NHBS cycle, 1-year change in age (adjusted odds ratio [aOR] = 1.03, 95% confidence interval [CI] = 1.02, 1.05), female gender (aOR = 3.41, 95% CI = 2.48, 4.69), and change in education category (aOR = 1.19, 95% CI = 1.02, 1.39) were associated with a higher likelihood of having health insurance. In regression models that controlled for cycle, age, gender, and education, participants with health insurance were more likely than those without insurance to report seeing a medical provider in the past year (aOR = 3.49, 95% CI = 2.32, 4.66), ever having an HIV test (aOR = 1.52, 95% CI = 0.35, 2.69) and more frequent HIV testing in the past 2 years (incidence rate ratio [IRR] = 1.44, 95% = 1.14, 1.82). Participants with health insurance did not differ from those without insurance in number of vaginal condomless sex partners (IRR = 1.16, 95% CI = 0.95, 1.41) but did report more condomless anal sex partners in the past year (IRR = 1.97, 95% CI = 1.46, 2.65)., Conclusions: This study demonstrates how health insurance coverage is positively associated with HIV detection and prevention relevant to both US and international efforts to end the HIV epidemic., (© 2023. International Society of Behavioral Medicine.)