Boredom is closely aligned with depression, but is understood to be conceptually distinct. Little is known about boredom among active drug users and the potential association with depression and HIV risk. Current IDUs (n = 845) completed a baseline behavioral survey including socio-demographic characteristics, self-reported boredom, depressive symptoms (CESD score), and HIV risk behaviors. One-third of the sample reported high boredom in the past week. In multivariate analysis, those who reported boredom were less likely to be older, African-American, have a main partner, and to be employed at least part-time. Controlling for covariates, those with high boredom were almost five times as likely to report high depressive symptoms. Co-occurrence of boredom and depressive symptoms (28 %) was strongly and independently associated with a range of injection risk behaviors and sex exchange. This study demonstrates the need for more thorough understanding of mental health and HIV risk among urban drug users.