Restorative proctocolectomy with ileal pouch-anal anastomosis with or without mucosectomy has become the procedure of choice in patients with long-standing ulcerative colitis complicated by malignancy or medically refractory disease and for familial polyposis syndrome. Some reports have demonstrated the development of malignancy at the ileoanal anastomosis. We present a recent series of five patients who developed adenocarcinoma in the middle of their ileal pouch including the first case of pouch carcinoma in a patient who underwent pouch formation for ulcerative colitis. We discuss their presentation and management. Development of ileal pouch cancers, while rare, has been seen with increasing frequency in our practice. Patients with long-standing ileal pouches may benefit from routine surveillance of the pouch as often as every six months, which can be performed quickly and easily in the office using flexible endoscopy.