When an initial antiretroviral (ART) regimen is effective and well-tolerated, it can be maintained for years as long as the patient adheres. Prior research has revealed that shorter initial ART duration is associated with regimen type, female sex, injection drug use (IDU) as the HIV transmission risk factor, and lower baseline CD4 count. We examined initial ART duration in ART-naïve individuals newly enrolling in HIV care in the DC Cohort. We included ART naïve-individuals with detectable HIV RNA enrolled in the DC Cohort after January 2011 with >6 months of follow-up. The outcome of interest was the discontinuation of the initial regimen. Kaplan Meier analysis and Multivariable Cox PH modeling were performed. There were 479 individuals included in the analysis. The median age of participants was 33.9 years (IQR 26-43.9). The sample was predominantly male (79.1%) and of Black race (70.8%). Over half of the study participants (56.4%) attended community-based clinic sites. The median time to the discontinuation of initial ART was 2.7 years (95% CI: 2.3, 3.4). Females had a shorter time to ART discontinuation (aHR 1.55, 95% CI: 1.14, 2.11) as did individuals who started on a PI-based regimen vs INSTI (aHR 1.87, 95% CI: 1.34, 2.61), and those receiving HIV care at a community-based site (aHR 1.46, 95% CI: 1.11,1.93). Although limited by lack of reason for discontinuation, we demonstrated that ART-naïve women, community clinic attendees, and patients starting on PIs had shorter duration of initial ART. More anticipatory guidance may be needed to help patients stay on their initial therapy and manage the side effects or to be flexible in trying different regimens.