Much research has examined the relationship between depressive symptoms and unprotected sex among men who have sex with men (MSM), but little is known about how depression is related to the sexual behavior of men who intentionally engage in unprotected anal intercourse, or bareback sex. In this study, we explored the extent to which depressive symptoms were associated with rates of unprotected sex among barebackers, and whether this relationship was dependent upon HIV serostatus. Using a sample of 120 MSM who engage in intentional condomless sex, we found that for HIV-negative participants, depressive symptoms were associated with the overall frequency of unprotected anal intercourse as well as unprotected anal intercourse with a serodiscordant partner. For HIV-positive participants, depressive symptoms were not associated unprotected intercourse. Additional research is needed to better understand depression among men who bareback and how interventions could be designed to address depression and reduce sexual risk behaviors.