There is an increased prevalence of HIV among incarcerated populations. We conducted a rapid HIV testing pilot program using oral specimens at the Rhode Island Department of Corrections (RIDOC) jail. Detainees (N = 1,364) were offered rapid testing upon jail entrance and 98% completed testing. Twelve detainees had reactive rapid tests, one of which was a new HIV diagnosis. To evaluate the program qualitatively, we conducted key informant interviews and focus groups with key stakeholders. There was overwhelming support for the oral fluid rapid HIV test. Correctional staff reported improved inmate processing due to the elimination of phlebotomy required with conventional HIV testing. Delivering negative rapid HIV test results in real-time during the jail intake process remained a challenge but completion of confirmatory testing among those with reactive rapid tests was possible. Rapid HIV testing using oral specimens in the RIDOC jail was feasible and preferred by correctional staff.