The 2021 Sexually Transmitted Infectious (STI) Guidelines advise syphilis screening every 3-6 months despite a surge of rapid-onset syphilis symptoms in men who have sex with men (MSM) infected with human immunodeficiency virus (HIV). A retrospective chart review of the HIV Clinic Care Registry at Jerry L. Pettis Memorial Veterans Administration Medical Center (JLP VAMC) was conducted from 2002 to 2016. In 2004, Rapid Plasma Reagin (RPR) assay screening changed yearly to every 3 months. A total of 155 cases of syphilis occurred in 126 HIV-infected men; 81% were MSM, and 69% had prior syphilis. As many as 54.8% were virally suppressed, and 57% had CD4 counts greater than 400. After switching from yearly to every three-month screening, the percentage of symptomatic patients decreased from 71.4% to 41.9%. Of the 26 episodes of neurosyphilis, 11 showed ocular involvement. Increased screening has reduced the prevalence of symptomatic syphilis. This study included many patients with both neurosyphilis and ocular syphilis. Shortening the screening intervals in MSM and HIV-infected individuals will help to identify patients prior to developing symptomatic syphilis.