Background: Patient safety is among the main goals in a health system. Medical errors are considered a significant threat to patient safety. An effective strategy to reduce this risk is reporting these errors even when the patient is not affected. This study investigated the main barriers to reporting medical errors and related factors. Methods: This cross-sectional descriptive study was conducted in academic hospitals afflicted with Guilan University of Medical Sciences (GUMS) in 2020. University faculty members and residents enrolled in the survey, and a questionnaire was filled out via a face-to-face interview by the responsible resident of anesthesiology. Results: Overall, 366 individuals, 156 faculty members, and 210 residents completed the questionnaires. Overall, 271 (74.2%), 134 (85.9%) faculty members, and 137 (65.6%) residents, the main barrier to report medical errors was concerning legal consequences. Furthermore, the other important factors were concerning losing job credit (63.4%) and losing the patient’s trust (61.2%). Moreover, the main predisposing factors of medical errors were high workload and a large number of patients (83.3%), long work shifts, and physicians fatigue (80.8%). High job stress and the lack of feeling of support from higher authorities (70.5%), and the lack of adequate equipment and appropriate medical facilities (56%) were the most related factors based on their perspective. Conclusion: According to the obtained findings, the main barrier to reporting medical errors was legal consequences. Moreover, the main predisposing factors were high workload, many patients, long working shifts, and physicians’ fatigue. Attempts should be made to plan programs to improve the current conditions.