To successfully implement the Seek, Test, and Treat (STT) strategy to curb the HIV epidemic, the criminal justice system must be a key partner. Increasing HIV testing and treatment among incarcerated persons has the potential to decrease HIV transmission in the broader community, but whether it is feasible to consider the implementation of the STT within jail facilities is not known. We conducted a retrospective review of Rhode Island Department of Corrections (RIDOC) medical records to assess whether persons newly diagnosed in the jail were able to start ART and be linked to community HIV care after release. From 2001 to 2007, 64 RIDOC detainees were newly diagnosed with HIV. During their index incarcerations, 64% were informed of positive confirmatory HIV test results, 50% completed baseline evaluations, and 9% began ART. Linkage to community care was confirmed for 58% of subjects. Subjects incarcerated for >14 days were significantly more likely to receive HIV test results and complete baseline evaluation (p<0.001). A similar association was not observed for ART initiation until incarceration length reached 60 days (p<0.001). There was no association between incarceration length and linkage to care. This comprehensive analysis demonstrates that length of incarceration impacts HIV test result delivery, baseline evaluation, and ART initiation in the RIDOC. Jails are an important venue to "Seek" and "Test"; however, completing the "Treat" part of the STT strategy is hindered by the transient nature of this criminal justice population and may require new strategies to improve linkage to care.