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Chronic ulcerative colitis (UC) is a risk factor for malignancy in longterm disease process. Obstruction, perforation, and hemorrhage are the possible emergency situations in colorectal malignancy. A 68-year-old male with chronic UC for 18 years with steroiddependent disease (on 10 mg prednisolone daily) presented with acute pain abdomen with distention not passing stool or flatus for 2 days. Diagnosed to have perforated sigmoid malignancy, underwent Hartmann's procedure. Following the adjuvant therapy, the patient denied any definitive surgery and opted to stay on Colorectal Cancer Surveillance Programme. At present, patient's positron emission tomography/computed tomography shows pelvic, liver surface, and small bowel deposits, suggestive of recurrence or metastasis. This case report is discussed to emphasis the importance of aggressive surgical treatment in longterm steroiddependent disease and poor prognosis of perforated malignancy irrespective of pathological staging.