Complicated subacute diverticulitis may mimic colorectal cancer, representing a significant diagnostic challenge in surgical practice. We report the case of a 69-yearold woman with a history of chronic diarrhea, unintentional weight loss exceeding 10 kg, and diffuse abdominal pain. Diagnostic investigation revealed a rectosigmoid stricture with an infiltrative appearance on colonoscopy and circumferential wall thickening with upstream bowel dilation on computed tomography, raising strong suspicion of locally advanced colorectal cancer. Endoscopic biopsies were inconclusive, showing only granulation tissue, and carcinoembryonic antigen levels were within normal limits. Given the diagnostic uncertainty, an oncologic surgical approach was adopted, and the patient underwent rectosigmoid resection with Hartmann’s procedure. Histopathological analysis of the surgical specimen demonstrated acute diverticulitis associated with diverticular disease, with no evidence of malignancy. The patient had an uneventful postoperative recovery and was discharged on the eighth postoperative day. This case highlights the limitations of current diagnostic methods in differentiating complicated diverticulitis from colorectal cancer and reinforces the importance of an appropriate surgical approach when malignancy cannot be excluded.