In India men who have sex with men (MSM) are stigmatized, understudied, and at high risk for HIV. Understanding the impact of psychosocial issues on HIV risk behavior and HIV infection can help shape culturally relevant HIV prevention interventions. Peer outreach workers recruited 210 MSM in Chennai who completed an interviewer-administered psychosocial assessment battery and underwent HIV testing and counseling. More than one fifth (46/210) reported unprotected anal intercourse in the past 3 months, 8% tested positive for HIV, and 26% had previously participated in an HIV prevention intervention. In a multivariable logistic-regression model controlling for age, MSM subpopulation (kothi, panthi, or double-decker), marital status, and religion, significant predictors of any unprotected anal intercourse were being less educated (adjusted odds ratio [AOR] = .54; p = .009), not having previously participated in an HIV prevention program (AOR = 3.75; p = .05), having clinically significant depression symptoms (AOR = 2.8; p = .02), and lower self-efficacy (AOR = .40; p < .0001). Significant predictors of testing positive for HIV infection were: being less educated (AOR = .53; .05) and not currently living with parent(s) (AOR = 3.71; p = .05). Given the prevalence of HIV among MSM, efforts to reach hidden subpopulations of MSM in India are still needed. Such programs for MSM in India may need to address culturally-relevant commonly cooccurring psychosocial problems to maximize chances of reducing risk for infection.