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Pati Aji Achdiat, Alvi Alvarani, Rievanda Ayu Natasya, Retno Hesty Maharani Department of Dermatology and Venereology, Faculty of Medicine, Universitas Padjadjaran - Dr. Hasan Sadikin Hospital, Bandung, IndonesiaCorrespondence: Pati Aji Achdiat, Department of Dermatology and Venereology, Faculty of Medicine, Universitas Padjadjaran - Dr. Hasan Sadikin Hospital, Jl. Pasteur 38, Bandung, West Java, 40161, Indonesia, Email pati.aji.achdiat@unpad.ac.id Retno Hesty Maharani, Department of Dermatology and Venereology, Faculty of Medicine, Universitas Padjadjaran - Dr. Hasan Sadikin Hospital, Jl. Pasteur 38, Bandung, West Java, 40161, Indonesia, Email retno.hesty@unpad.ac.idAbstract: Syphilis is a sexually transmitted infection caused by Treponema pallidum, primarily transmitted by sexual intercourse. Secondary syphilis is characterized by lesions on the skin and mucosal membranes, including condyloma lata (CL), occurring in 17% of secondary syphilis cases. Papules or flat-colored skin plaques are characteristic of CL. They are typically found in humid regions, such as skin folds, including the labia majora, perianal area, axilla, interdigital spaces, and inframammary folds. Presentation in an open region of the body, such as the nipple and the surrounding area of the breast, is rare. Herein we report a case of a 30-year-old female presenting with papules on both breasts and roseola syphilitica with Biett’s collarette on both palms and soles that had not been pruritic nor painful for three weeks. The patient has been treated for human immunodeficiency virus (HIV) for the past year. The patient was involved in prostitution for three years, with a total of 6 sexual partners. T. pallidum Hemagglutination Assay (TPHA) and the Venereal Disease Research Laboratory (VDRL) were reactive, with a VDRL titer of 1:8. The patient received a single dose of benzathine penicillin 2.4 million IU injected intramuscularly. The histopathology examination from papules on the breast confirmed the diagnosis of CL, which revealed lymphoplasmacytic infiltrates around the blood vessels and plump endothelial cells. The skin-colored papules on both areolas and the rash associated with secondary syphilis on both palms and soles began to fade two weeks after the intramuscular injection of single dose benzathine penicillin 2.4 million IU. Unusual presentation of secondary syphilis outside predilection sites is possible. A high degree of suspicion is warranted when unusual papules are present, especially with a background of multiple sexually transmitted diseases and immunocompromised condition.Keywords: areolar, breast, condyloma lata, syphilis, human immunodeficiency virus