There have been nearly 1,600 new diagnoses of Human Immunodeficiency Virus (HIV) across the US Armed Forces between 2017 and 2022. While treatment has improved overall survival, self-perception of acquiring HIV may not align with actual risk of acquiring HIV, thus slowing diagnosis and treatment. We aim to evaluate self-perceived risk (SPR) versus calculated risk (CR) of HIV infection in US Air Force (USAF) members with incident HIV diagnosis. All USAF members with new HIV diagnosis evaluated at a specialty care military medical center between January 2015 and March 2020 with case report forms were included (n = 142). SPR was compared to CR using the Denver HIV Risk Score (DHRS). The study was approved by the Army Public Health Center's Public Health Review Board (#14-311) and the Walter Reed Army Institute of Research Human Subjects Protection Branch (#1861E). Patients were predominantly male (98%), with a median age of 26 (IQR 22-30) years, and the majority (85%) reported same-sex partners. Most patients reported a low SPR (n = 78; 55%). A higher proportion of low SPR patients were married or partnered than high SPR patients (29% versus 14%; P = 0.04). Both groups had median DHRS scores in the highest risk category with similar results by reason for HIV screening. The majority of USAF members with incident HIV infection reported a low SPR despite risk factors and CRs identical to high SPR patients. In order to inform HIV prevention strategies in the military, further efforts are needed to educate the military population and providers about HIV risk perception.