This study aimed to determine whether the number of diverticulitis or complicated diverticulitis episodes affects the conversion rate or postoperative complication rate in elective laparoscopic sigmoid colectomy. In this study, 216 charts were reviewed for baseline characteristics, diverticulitis history, and intra- and postoperative complications. Analysis was performed with the Student’s t-test, the chi-square test, and Fisher’s exact tests. Of 216 sigmoid colectomies, 151 were laparoscopic, 19 were converted, and 46 were open. Baseline characteristics were similar for patients with zero to two and those with three or more inpatient diverticulitis attacks. Patients with uncomplicated diverticulitis had a higher rate of conversion after three or more inpatient episodes (2.6% vs 25%; p = 0.04). There was no difference in operative times or postoperative complication rates. Patients with a history of abscess had a 23% chance of conversion. Those with no abscess history had an 8% chance of conversion (p = 0.02). In general, converted procedures required more time than open procedures but were associated with decreased hospital length of stay (LOS) and a decreased rate of postoperative ileus. Multiple inpatient diverticulitis attacks and a history of abscess were associated with laparoscopic conversion. Converted procedures required more time than open procedures, but had reduced LOS and postoperative ileus. Laparoscopic sigmoid colectomy can be attempted safely for patients with three or more inpatient attacks or a history of complicated diverticulitis.