Hospitalized patients are exposed to more than 1 medication error per day, but there are limited data concerning the factors associated with medication order errors made by general surgery residents. The objective of this study was to identify patterns in medication order errors amongst general surgery residents, which may provide educational targets to reduce medication errors by this population of providers. This study used a retrospective cohort design to review inpatient medication orders placed via a computerized physician order entry system by general surgery residents at a single academic medical center from July 2011 to February 2018. A single large academic medical center located in the Midwest, United States. General surgery residents completing residency between July 2011 and February 2018 and their respective inpatient medication orders. Of 571,811 included medication orders placed by 169 unique general surgery residents, 4.2% (n = 24,177) triggered pharmacist intervention, and 11 (0.001%) resulted in significant near-miss events. Of orders requiring pharmacist intervention, most were either duplicate therapies (n = 8703, 36.1%) or errors in renal dosing (n = 7576, 31.3%). Error rates were higher within pharmaceutical classes ordered less frequently, with the notable exception of antimicrobials and anticoagulants, which accounted for 20.1% (n = 5280) and 13.5% (n = 3270) of all order errors, respectively. In a multivariable model, errors were more likely to occur in the intensive care unit versus other units (OR = 1.21, 95%CI = 1.14-1.29) and in August versus other months (OR = 1.09, 95%CI = 1.01-1.17), but were independent of other resident and order characteristics. This study identified that resident medication order errors are common and are associated with specific therapeutic classes, the beginning of academic years, and intensive care unit patients. These findings represent potential targets for educational interventions and highlight the role of interdisciplinary teams in providing quality surgical care.