Since 2009, syphilis has been increasing in New York State (NYS) excluding New York City (NYC) among men with a history of male-to-male sexual contact (MSM). Because MSM make up a disproportionate number of new HIV infections, this study aims to: 1) establish yearly rates of early syphilis diagnosis, 2) assess factors associated with early syphilis diagnosis, and 3) describe missed opportunities for earlier diagnosis of syphilis among MSM living with diagnosed HIV(MSMLWDH) in NYS, excluding NYC. A cohort of adult MSMLWDH alive in 2013 were followed through 2016 to identify individuals with at least one early syphilis diagnosis between July 2014 and December 2016. Early syphilis diagnosis rates were calculated for 2015 and 2016. Crude relative risks and 95% confidence intervals were calculated to determine associations between available covariates and both syphilis diagnosis and missed opportunities. Missed opportunities were defined as reports of an HIV-related laboratory test within a given window corresponding to syphilis staging where syphilis testing was not performed at the same time. Of 7,512 MSMLWDH, 50.0% were non-Hispanic white, 85.4% aged ≥35, and 320(4.3%) had an early syphilis diagnosis. Yearly rates were: 1,838/100,000, and 1,681/100,000 in 2015 and 2016, respectively. Persons who were non-Hispanic black, living with diagnosed HIV for less than three years, aged <45, and were always virally suppressed or always in HIV care were significantly more likely to have a syphilis diagnosis. Over half of individuals had evidence of a missed opportunity for earlier syphilis diagnosis. Syphilis stage at diagnosis, older age, and syphilis diagnosis not concurrent with an HIV-related laboratory test were associated with a higher likelihood of having a missed opportunity. This study supports high interrelatedness of the syphilis and HIV epidemics among MSM. Since syphilis can impact HIV viral load suppression status, efforts to end the HIV epidemic need to be coupled with syphilis elimination efforts.