Pleomorphic lobular carcinoma of the breast has been identified as a histological variant of infiltrating lobular carcinoma (ILC) with poor prognosis. Thus, cytological recognition of this tumour is important. It is characterized by pleomorphism to a degree that contrasts with the cytologic uniformity of classic ILC. Due to this feature it is often misinterpreted as infiltrating ductal carcinoma and diagnosed only on appreciating the Indian file and targetoid pattern of lobular carcinomas on histology. We report three cases with this unusual tumour that can present a diagnostic dilemma on cytology.