The development of acute large bowel obstruction secondary to colorectal cancer is very common and, while right hemicolectomy with a primary anastomosis is the accepted procedure for right-sided obstructing tumors, the different strategies performed for left-sided tumors, including staged procedures, Hartmann's procedure, and resection with anastomosis, remain a subject of controversy. We present herein the case reports of three patients who developed two synchronous occlusive tumors of the large bowel. Complete exploration of the entire colon is highly recommended to assess the most feasible therapeutic option in such cases, as the second occlusive tumor, often hidden within the bowel segments, can cause failure of limited resection or intestinal decompression.