Background: The rate of biliary injuries from minimally invasive cholecystectomy has remained high for over two decades. To improve outcomes there are multiple bail-out methods described, including aborting the procedure, converting to open, or performing a sub-total cholecystectomy. However, the intraoperative difficulty threshold for when a bail-out method should be implemented is poorly understood. Methods: From 1/2014 to 2/2019 cholecystectomy videos were collected, de-identified, edited to include the 2–3 minutes when the gallbladder was first visualized, and accelerated. They were then rated on a 5-point difficulty scale. Inter-coder reliability was evaluated using Krippendorff's alpha and regression models were used to evaluate the scores ability to predict the need for a bail-out technique. Results: 62 videos were analyzed with a median length after editing of 37.5 (29.0–43.3) seconds. A median time of 46.2 (38.3–53.4) seconds was required for grading. The bail-out rate was 42.9%. The inter-coder reliability between 2 surgeons and 8 non-clinical reviewers was 0.675 with an average difficulty score of 3.0 (SD = 1.01). Regression models showed that the scale was able to significantly predict conversion (β=0.56,p<.01). Conclusion: This novel difficulty score was able to predict conversion to a bail-out technique early in the course of minimally invasive cholecystectomy.