This is a case of a laparoscopic sigmoid and small bowel resection with two intracorporeal anastomosis for diverticulitis complicated by both an abscess and coloenteric fistula discovered intraoperatively. A 43-year-old male with no past medical history presented with an acute episode of diverticulitis. Imaging revealed a 6.5 cm pelvic abscess not amendable to percutaneous drainage due to it being surrounded by loops of bowel. The patient recovered well on antibiotics. An elective resection was planned due to the patient complaining of recurring pain. Preoperative CT demonstrated resolution of the abscess. A standard laparoscopic sigmoidectomy was planned. After the abdomen was entered, dense adhesions of diseased colon to bladder, pelvic wall, and small bowel were encountered. A coloenteric fistula was found after adhesiolysis. The decision was then made to perform an en bloc resection of the involved small bowel. The fistulized small bowel was then resected with a stapler and ligasure (~3 cm of small bowel). The descending colon was then mobilized. The diseased sigmoid colon was then isolated. The distal specimen was stapled off and an extraction incision was made. The diseased sigmoid colon along with the small bowel specimen were brought out and stapled off. An intracorporeal small bowel side-to-side, end-to-end stapled anastomosis was then performed. The enterotomy was sutured closed in 2 layers. The colorectal anastomosis was then created using an EEA stapler. The patient tolerated the procedure and postoperative course well without any complications.