A 50-year-old man presented to the surgery clinic with a 1-month history of painful hematochezia. One month before the onset of his symptoms, he had had condomless receptive anal intercourse with a new partner. He reported no fever, weight loss, rashes, genital lesions, or change in bowel habits. A physical examination was normal. Serologic testing was notable for a positive Treponema pallidum particle agglutination assay, a rapid plasma reagin (RPR) titer of 1:32, and a negative human immunodeficiency virus test. A sample obtained from a rectal swab was negative for chlamydia and gonorrhea. A subsequent colonoscopy identified an ulcer measuring 3 cm in diameter in the distal rectum with edematous, friable mucosa and some bleeding (Panel A). Histopathological examination of a biopsy specimen showed histiocytes and lymphoplasmacytic infiltrates in the lamina propria and submucosa, no granulomas or neoplasia, and numerous spirochetes within the lamina propria on immunohistochemical staining for T. pallidum (Panel B). A diagnosis of syphilitic proctitis was made. After treatment with benzylpenicillin, the patient’s symptoms abated. A repeat RPR titer was 1:8, and a repeat colonoscopy showed resolution of the rectal ulcer (Panel C).