Recidivism is a pervasive problem facing the incarcerated. Incarcerated persons who are human immunodeficiency virus (HIV)-infected often have multiple risk factors associated with initial incarceration and recidivism, in particular, injection drug use. Yet, some jails provide case management for HIV-infected inmates to provide continuity of health care, which might have positive effects on reentry into the community. We sought to measure recidivism and factors related to recidivism in an HIV-infected cohort in an urban county jail with an active case management program. Fifty-two inmates surveyed in 1999 at the San Francisco County Jail were followed for rearrests through 2006. In follow-up, 73% were re-incarcerated on an average of 6.8 times for 552 days. Risk factors included nonwhite ethnicity, history of homelessness and crack use, common risk factors for incarceration. Less than high school education was associated with recidivism, shorter time to reincarceration, and more incarcerations. HIV-infected inmates spend a high proportion of time in multiple incarcerations, a reflection of the cyclical nature of incarceration despite comprehensive case management. Well-known risk factors for incarceration were associated with recidivism; in addition, lack of high school education played a prominent role. Education should be explored as a way to make further progress on breaking the cycle of incarceration.