Primary neoplasms arising in the anal canal are relatively unusual.In particular, adenomas and adenocarcinomas are distinctly rare entities in this region.We describe an infiltrating, well-differentiated adenocarcinoma arising in a villous adenoma from the distal anal canal, in an otherwise healthy patient at low risk for gastrointestinal malignancy.This is the case of an octogenarian man with a several year history of hemorrhoids and intermittent rectal bleeding, more recently complaining of continuous hematochezia.Examination revealed a blood-covered pedunculated mass with a long stalk protruding from the anus.The lesion was amputated at the bedside.Microscopic evaluation revealed an infiltrating well-differentiated adenocarcinoma, arising from a villous adenoma.This was further evaluated under anesthesia and complete excision of distal anal tissue was performed.Our report is the f irst describing the possible malignant degeneration of a villous adenoma in the anal canal. Primary neoplasms arising in the anal canal are relatively unusual. In particular, adenomas and adenocarcinomas are distinctly rare entities in this region. We describe an infiltrating, well-differentiated adenocarcinoma arising in a villous adenoma from the distal anal canal, in an otherwise healthy patient at low risk for gastrointestinal malignancy. This is the case of an octogenarian man with a few years history of hemorrhoids and intermittent rectal bleeding, more recently complaining of continuous hematochezia. Examine revealed a blood-covered pedunculated mass with a long stalk protruding from the anus The lesion was amputated at the bedside. Microscopic defibrillation revealed an infiltrating well-differentiated adenocarcinoma, arising from a villous adenoma. This was further evaluated under anesthesia and complete excision of distal anal tissue was performed. Our report is the f irst describing the possible malignant degeneration of a villous adenoma in the anal canal.