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Colorectal cancers are more common in the West than in Asian subcontinent. An increasing trend in the occurrence of colorectal signet cell carcinomas has been observed, exhibiting association with inflammatory bowel disease. Its distinct clinical features, pathognomonic, histologic, and radiologic appearance make it an unmissable entity. We report two such cases in the background of inflammatory bowel disease. We aim to familiarize our readers with its cross-sectional imaging features.