Complicated left-sided colonic acute diverticulitis represents one of the most common diseases of surgical interest in the emergency department, with a mortality reaching 30% in cases of diffuse peritonitis. The best surgical strategy should minimize mortality rates and preserve the best possible quality of life. The Hartmann’s procedure is widely adopted but is associated with high morbidity and very low colostomy reversal rates. Recent literature suggests that resection with primary anastomosis and proximal diversion presents the optimal operative procedure whenever patient’s clinical conditions allow for it. In cases of severe septic shock, a damage control laparotomy should be considered, in order to reduce mortality and definitive stoma rates. In cases of large bowel obstruction due to diverticular stenosis, self-expanding metal stent as bridge to surgery could be an option, but upfront surgery is the preferable strategy.