We report a case of noduloulcerative tertiary syphilis that had gone misdiagnosed as discoid lupus erythematosus for many years. This case is noteworthy for (1) a Jarisch-Herxheimer-like reaction, (2) a dramatic response to penicillin therapy despite the presence of long-standing disease, and (3) posttreatment granulomas of possible hypersensitivity origin.