Substantial increases in syphilis during 2008-2013 were reported in the US Pacific Northwest state of Oregon, especially among men who have sex with men (MSM). The authors aimed to characterize the ongoing epidemic and identify possible gaps in clinical management of early syphilis (primary, secondary, and latent syphilis ≤1 year) among MSM in Multnomah County, Oregon to inform public health efforts. Administrative databases were used to examine trends in case characteristics during 2008-2013. Medical records were abstracted for cases occurring in 2013 to assess diagnosis, treatment, and screening practices. Early syphilis among MSM increased from 21 cases in 2008 to 229 in 2013. The majority of cases occurred in HIV-infected patients (range: 55.6%-69.2%) diagnosed with secondary syphilis (range: 36.2%-52.4%). In 2013, 119 (51.9%) cases were diagnosed in public sector medical settings and 110 (48.0%) in private sector settings. Over 80% of HIV-infected patients with syphilis were in HIV care. Although treatment was adequate and timely among all providers, management differed by provider type. Among HIV-infected patients, a larger proportion diagnosed by public HIV providers than private providers were tested for syphilis at least once in the previous 12 months (89.6% vs. 40.0%; p < 0.001). The characteristics of MSM diagnosed with early syphilis in Multnomah County remained largely unchanged during 2008-2013. Syphilis control measures were well established, but early syphilis among MSM continued to increase. The results suggest a need to improve syphilis screening among private clinics, but few gaps in clinical management were identified.