(1) Background: The difficulty of pelvic operation is greatly affected by anatomical constraints. Defining this difficulty and assessing it based on conventional methods has some limitations. Artificial intelligence (AI) has enabled rapid advances in surgery, but its role in assessing the difficulty of laparoscopic rectal surgery is unclear. This study aimed to establish a difficulty grading system to assess the difficulty of laparoscopic rectal surgery, as well as utilize this system to evaluate the reliability of pelvis-induced difficulties described by MRI-based AI. (2) Methods: Patients who underwent laparoscopic rectal surgery from March 2019 to October 2022 were included, and were divided into a non-difficult group and difficult group. This study was divided into two stages. In the first stage, a difficulty grading system was developed and proposed to assess the surgical difficulty caused by the pelvis. In the second stage, AI was used to build a model, and the ability of the model to stratify the difficulty of surgery was evaluated at this stage, based on the results of the first stage; (3) Results: Among the 108 enrolled patients, 53 patients (49.1%) were in the difficult group. Compared to the non-difficult group, there were longer operation times, more blood loss, higher rates of anastomotic leaks, and poorer specimen quality in the difficult group. In the second stage, after training and testing, the average accuracy of the four-fold cross validation models on the test set was 0.830, and the accuracy of the merged AI model was 0.800, the precision was 0.786, the specificity was 0.750, the recall was 0.846, the F1-score was 0.815, the area under the receiver operating curve was 0.78 and the average precision was 0.69; (4) Conclusions: This study successfully proposed a feasible grading system for surgery difficulty and developed a predictive model with reasonable accuracy using AI, which can assist surgeons in determining surgical difficulty and in choosing the optimal surgical approach for rectal cancer patients with a structurally difficult pelvis.