Gross intraoperative assessment can be used to ensure negative margins at the time of surgery. Previous studies of this technique were conducted before the introduction of consensus guidelines defining a “positive” margin. We performed a retrospective study examining the accuracy of this technique since these guidelines were published. We identified all specimens that were grossly examined at the time of breast conserving surgery from January 2014 to July 2020. Gross and final microscopic diagnoses were compared and the performance of intraoperative examination was assessed in terms of false positive and false negative rates. Logistic regression models were used to examine the effect of clinicopathologic covariates on discordance. 327 cases were reviewed. Gross exam prompted re-excision in 166 cases (61%). The rate of false negative discordance was 8.6%. In multivariate analysis, multifocality on final pathology was associated with discordance. We consider the false negative rate acceptable for routine clinical use; however, there is an ongoing need for more accurate methods for the intraoperative assessment of margins.