Although criminal justice involvement has repeatedly been associated with human immunodeficiency virus (HIV)/sexually transmitted infection prevalence and sexual risk behaviors, few studies have examined whether arrest or incarceration uniquely contributes to sexually risky behavior. We examined the temporal relationship between criminal justice involvement and subsequent sexual HIV risk among men in methadone maintenance treatment in New York City. A random sample of 356 men was interviewed at baseline (time 1), 6-month (time 2), and 12-month (time 3) follow-ups. Propensity score matching, negative binomial, and multiple logistic regression were used to isolate and test the effect of time 2 arrest and incarceration on time 3 sexual risk behaviors. Incidence of time 2 criminal justice involvement was 20.1% for arrest and 9.4% for incarceration in the prior 6 months. Men who were arrested at time 2 demonstrated increased number (adjusted incidence rate ratio [IRR]=1.62; 95% confidence intervals [CI]=1.11, 2.37) and proportion (IRR=1.36; 95% CI=1.07, 1.72) of unprotected vaginal sex acts at time 3. Men incarcerated at time 2 displayed increased number (IRR=2.07; 95% CI=1.23, 3.48) and proportion (IRR=1.45; 95% CI=1.06, 1.99) of unprotected vaginal sex acts at time 3. Within this sample of drug-involved men, arrest and incarceration are temporally associated with and may uniquely impact successive sexual risk-taking. Findings underscore the importance of HIV prevention interventions among individuals with low-intensity criminal justice involvement. Developing prevention efforts aimed at short-term incarceration, community reentry, and alternatives to incarceration settings will address a large and under-researched segment of the criminal justice population. Alternative approaches to current criminal justice policy may result in public health benefits