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Papillary lesions of the breast pose great diagnostic challenges on fine needle aspiration cytology (FNAC) due to overlapping features between benign and malignant entities. Preoperative cytodiagnosis is difficult. We present a case of a 52-year-old male who presented with a progressively increasing firm swelling in the left breast for 3 years. The nipple was eroded with ulceration and bleeding. Ultrasonography (USG) revealed a mass measuring 2.9 cm × 1.5 cm in the left breast. FNAC smears were hypercellular with ductal cells arranged in papillae and glandular clusters. At places, the cells had irregular nuclear membrane, prominent nucleoli, fine chromatin, scanty-to-moderate cytoplasm, and high nuclear-cytoplasmic ratio with pleomorphism. Histopathology of the excised swelling was consistent with intracystic papillary carcinoma (IPC) supported with immunohistochemistry markers. The case is being presented due to its rarity.