Two cases of late cutaneous syphilis are presented. After treatment for secondary syphilis in 1957 and retreatment for rising VDRL titers ten years later, one patient had developed a nodular syphilid. The other had several gummas. He had two quantitative nonreactive vDRL tests and a negative Treponema pallidum immobilization (TPI) test, but two reactive fluorescent treponemal antibody absorption (FTA-ABS) tests. Syphilis was suspected histologically and was confirmed by the specific serologic testing, the characteristic clinical presentation, and the prompt response to penicillin treatment. The clinical, serologic, histologic, therapeutic, and pathogenetic aspects of late benign syphilis of the skin are discussed.