Introduction Although mortality rates after esophagectomy have decreased over the last 30 years, anastomotic leaks still commonly persist and portend significant morbidity. Previous studies have analyzed patient and perio-perative risk factors for leaks, yet data describing the association of leaks and an open or minimally invasive approach are lacking. The purpose of this study was to evaluate the impact of operative approach on leak rates and subsequent management of the leaks. Methods We queried the Procedure-Targeted National Surgical Quality Improvement Program Database for patients undergoing esophagectomy for cancer in the years from 2016 to 2019. Patient demographics, disease-related information, peri-operative data, and short-term outcomes were reviewed. Multivariable, stepwise logistic regression analysis was performed to investigate factors associated with post-operative anastomotic leaks. Results Of the 2696 patients who underwent esophagectomy for cancer, anastomotic leaks occurred in 374 (14%). Based on approach, 13% of open, 14% of laparoscopic, and 18% of robotic cases were complicated by leak ( P = .123). Multivariable analysis identified the following significant risk factors for leak: diabetes (OR 1.32, P = .047), hypertension (OR 1.32, P = .022), and longer operative time (OR 1.61, P < .001). The percentage of leaks requiring endoscopic or operative intervention was 75% for open, 79% for laparoscopic, and 54% for robotic cases ( P = .004). Conclusions Anastomotic leaks after esophagectomy for cancer occur frequently regardless of surgical approach. Furthermore, these leaks are managed differently after an open, laparoscopic, or robotic approach. Robotic esophagectomies complicated by anastomotic leak required less invasive management.