© 2018, Springer Science+Business Media, LLC, part of Springer Nature. Sexual transmission risk occurs in the context of serodiscordant condomless anal intercourse (CAI) where the seropositive partner is virologically detectable (VL+) and/or seronegative partner is not on PrEP. We analyzed correlates of serodiscordant CAI among 688 VL+ young men who have sex with men (YMSM). In multivariable analyses, serodiscordant CAI was associated with a receiving a HIV diagnosis in the past 6 months, greater depressive symptoms, and cocaine use during the past 90 days. Although HIV+ YMSM currently experience disparities across the continuum of care, those new to care may need support adopting risk reduction strategies with their sexual partners.