Background/Objectives: The Observational Clinical Human Reliability Assessment (OCHRA) system evaluates surgical performance by identifying intraoperative errors, yet evidence on error patterns and procedural safety in laparoscopic cholecystectomy (LC) remains limited. This study aimed to assess LC safety using established parameters and to describe intraoperative errors through the OCHRA system in patients with gallstone disease in Veracruz, Mexico. Methods: An observational, retrospective, analytical study was conducted between January 2022 and March 2025. Surgical videos from 11 surgical teams were reviewed. Intraoperative errors were classified using the OCHRA system across the three key steps of LC, while procedural safety was assessed through achievement of the Critical View of Safety (CVS) using the Doublet Photographic Score (DPS). Comparisons were performed according to the Parkland Grading Scale. Statistical analysis was conducted using SPSS version 26. Results: A total of 106 patients were included (67% women; mean age 45 ± 13 years; BMI 25.1 ± 3.2 kg/m²). Total LC was performed in 95% of cases and subtotal LC in 5%. Parkland grade 3 was the most frequent (32.1%). Overall, 3180 operative steps were evaluated, and 705 errors (22.1%) were identified. Procedural errors predominated across all phases (97–99%), mainly due to step repetition or additional steps, whereas execution errors were uncommon (1–3%). A satisfactory CVS was achieved in 54.7% of cases. No bile duct injuries were observed. Conclusions: The OCHRA system enabled detailed the identification of intraoperative error patterns and their relationship with surgical difficulty. Higher anatomical severity was associated with increased procedural errors and lower rates of adequate CVS achievement. These findings support structured video-based performance assessment as a complementary tool to established safety principles, with the potential to guide targeted training and improve surgical consistency in laparoscopic cholecystectomy.