Alopecia can be one of the many symptoms of secondary syphilis and the clinical presentations include essential syphilitic alopecia or symptomatic syphilitic alopecia. In this report, we present a case of a patient with essential syphilitic alopecia whose sole presenting symptom of syphilis was alopecia. Despite an initial negative rapid plasma reagin (RPR) test, he was ultimately found to have syphilis on scalp biopsy. His alopecia improved following treatment with benzathine penicillin. This presentation serves as a reminder to clinicians to be cognizant of alopecia as a presenting sign of syphilis. A review of the specificity and sensitivity of the typical tests used for the diagnosis is presented.