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Background: Although an Observed Structured Clinical Examination (OSCE) has been used to evaluate patient interaction and general knowledge competencies of third-year students during their required surgical clerkships, whether surgical clerkship experience predicts satisfactory performance with a surgical patient in an OSCE environment has not been investigated., Objective: We hypothesized that completion of the third-year surgery clerkship would improve student ability to diagnose acute cholecystitis and recognize the further need for hospital admission and treatment., Design: An observational study design was used to determine student skills in evaluating a simulated surgical patient with abdominal pain from acute cholecystitis. The skills included key data gathering, physical examination, and information-sharing tasks., Setting: Tertiary care academic medical center., Participants: Performance was compared between a cohort of 101 medical students who had completed the third-year surgical clerkship and 72 who had not. A secondary analysis compared performance for 91 students who had completed their third-year clerkship in sites near the University of California, San Francisco School of Medicine, and 10 who did so at a regional campus geographically distant from the medical school., Results: Of the 173 students who participated in the OSCE, only 42% correctly identified the diagnosis of acute cholecystitis, though 71% did suggest the possibility of a biliary process to the standardized patient. Most of the students who identified the condition as acute cholecystitis or gallbladder-related process had completed their third-year surgical clerkship (odds ratio [OR] = 3.26). Students who completed their surgical clerkship were also better able to recommend appropriate treatment for the patient (OR = 2.35), and recommend admission to the hospital or emergency department (OR = 2.00). Approximately one-third (35.3%) of all students documented a positive Murphy's sign, but only 6.4% identified the triad of leukocytosis, fever, and a Murphy's sign as diagnostic of acute cholecystitis and the need for surgical intervention. Student performance on the clinical examination did not differ depending on whether the students completed their clerkship at a Bay Area or regional hospital., Conclusions: Student recognition of the key physical examination and laboratory findings diagnostic of acute cholecystitis was low, but students were better able to recommend further treatment for a patient with acute cholecystitis after completing the third-year surgical clerkship. Our study reveals areas where surgical educators can improve medical student ability to accurately diagnose acute cholecystitis and evaluate acute abdominal processes., (Copyright © 2015 Association of Program Directors in Surgery. Published by Elsevier Inc. All rights reserved.)