Incarcerated HIV-infected persons in San Francisco have benefited from intensive case management in jail and postrelease, which includes but is not focused on interventions to prevent transmission. In this population of predominately injection drug users (IDUs), we had the opportunity to examine interview data from 1999 and 2005 that included health characteristics and risk factors. Those in 2005 were less likely to be satisfied with social support and less likely to be partnered; more likely to have some form of health insurance. On average, health was perceived in both periods to be better the longer the person had been in jail. Injection drug use was reported lower in 2005, but a subset of nearly a quarter in each survey time period reported sharing needles. Persons in 2005 were less likely to report they always used condoms as compared to those in 1999 (odds ratio 0.26, 95% confidence interval 0.12-0.59, p = 0.001). While there were differences in study design and methodology, this comparison demonstrated overall similarities in characteristics of HIV-infected inmates. Findings echo those of others, in other populations of HIV-infected persons. Reasons could include HIV prevention fatigue or decay in effectiveness of prevention messages. Despite an established program for case management and links to services, renewed efforts are needed to maintain effectiveness of prevention strategies to this high-risk population.