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The release of the first drug for human immunodeficiency virus (HIV) preexposure prophylaxis (PrEP) in 2012 marked the beginning of a new era of HIV prevention. Although PrEP is highly efficacious, identifying and ultimately increasing uptake among the highest risk male subgroups remains a challenge.Public health surveillance data from 2009 to 2016 was used to evaluate the risk of an HIV diagnosis after a syphilis (ie, primary, secondary, or early latent), gonorrhea, and repeat diagnoses among urban males, including men who have sex with men (MSM) and non-MSM in Baltimore City.Of the 1531 males with 898 syphilis diagnoses and 1243 gonorrhea diagnoses, 6.8% (n = 104) were subsequently diagnosed with HIV. Within 2 years, 1 in 10 syphilis or gonorrhea diagnoses were followed by an HIV diagnosis among MSM, and 1 in 50 syphilis or gonorrhea diagnoses were followed by an HIV diagnosis among non-MSM. Among non-MSM with gonorrhea, the rate of HIV incidence was 5.36 (95% confidence interval, 2.37–12.14) times higher in those with (vs. without) a subsequent syphilis diagnosis or gonorrhea diagnosis.Local health care providers should offer PrEP to MSM diagnosed with syphilis or gonorrhea and to non-MSM with a previous gonorrhea diagnosis at time of a syphilis or gonorrhea diagnosis. The high proportion and short time to an HIV diagnosis among MSM after a syphilis or gonorrhea diagnosis suggest immediate PrEP initiation.