Linkage, engagement, retention and adherence to care are necessary steps along the HIV care continuum. Progression through these steps is essential for control of the disease and interruption of transmission. Identifying and re-engaging previously diagnosed but out-of-care patients is a priority to achieve the goals of the National HIV/AIDS strategy. Participants in the EnhanceLink cohort who were previously diagnosed HIV (n = 1,203) were classified as not-linked to of care and non-adherent to medication prior to incarceration by self report. Results based on multivariate models indicate that recent homelessness as well as high degrees of substance abuse correlated with those classified as not-linked to care and non-adherent to medications while having insurance was associated with being linked to care and adherent to care. The majority of detainees reported being linked to care but not currently adherent to care confirming that jails are an important site for re-engaging HIV individuals.