Background: Our institution utilizes an esophagectomy pathway to guide postoperative management. Our aim was to identify risk factors associated with missing pathway goals. Methods: Retrospective review of esophagectomies from 2010 to 2015. Multivariate logistic regression models identified risk factors for missing postoperative milestones prior to discharge. Odds ratios of variables affecting goals were calculated. Results: Of the195 esophagectomies, the most common risk factor for missing milestones was BMI, followed by operating room time, clinical stage, tobacco pack-years, and open surgical approach. Missing any milestone on the expected postoperative day significantly increase the odds of missing a future milestone, regardless of other risk factors. Conclusions: We have identified specific patient and operative factors that increase the risk of missing post-esophagectomy goals on time. Early identification of at-risk patients allows for pathway modification to avoid adverse outcomes and prolonged hospitalization. Analysis of meeting milestones early may allow for creation of accelerated pathways.