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Laparoscopic cholecystectomy (LC) is the standard technique for treatment of gallbladder disease. In case of acute cholecystitis we can identify preoperative factors associated with an increased risk of conversion and intraoperative complications. The aim of our study was to detect preoperative laboratory and radiological findings predictive of difficult LC with potential advantages for both the surgeons and patients in terms of options for management. We designed a retrospective case–control study to compare preoperative predictive factors of difficult LC in patients treated in emergency setting between January 2015 and December 2019. We included in the difficult LC group the surgeries with operative time > 2 h, need for conversion to open, significant bleeding and/or use of synthetic hemostats, vascular and/or biliary injuries and additional operative procedures. We collected 86 patients with inclusion criteria and difficult LC. In the control group, we selected 86 patients with inclusion criteria, but with no operative signs of difficult LC. The analysis of the collected data showed that there was a statistically significant association between WBC count and fibrinogen level and difficult LC. No association were seen with ALP, ALT and bilirubin values. Regarding radiological findings significant differences were noted among the two groups for irregular or absent wall, pericholecystic fluid, fat hyperdensity, thickening of wall > 4 mm and hydrops. The preoperative identification of difficult laparoscopic cholecystectomy provides an important advantage not only for the surgeon who has to perform the surgery, but also for the organization of the operating block and technical resources. In patients with clinical and laboratory parameters of acute cholecystitis, therefore, it would be advisable to carry out a preoperative abdominal CT scan with evaluation of features that can be easily assessed also by the surgeon.