Syphilitic chancres are pathognomonic of primary syphilis and can have many atypical presentations. Early detection of such lesions can prevent complications by linking patients to care early. We report a case of a 45-year-old Chinese men who has sex with men (MSM) presenting with a wound on his penis after masturbation. Initial impressions of a frenulum tear secondary to overzealous masturbation led to a circumcision and frenulectomy. Routine histology done provided an unexpected finding of plasma cell infiltrates suggestive of Syphilis. Serology was done to confirm the diagnosis and patient was treated with oral doxycycline for 2 weeks. This case aims to highlight the importance of routine histology during circumcisions especially because lesions such as syphilitic chancres are not always typical in presentation.