Objectives: Anastomotic complications represent a significant source of morbidity and occasionally mortality after esophagectomy. Since 2009, we have used a novel “side-to-side: staple line-on-staple line” (STS) technique for intrathoracic esophagogastric anastomoses, designed to create a wide-diameter esophagogastric anastomosis while preserving stomach conduit blood supply. In this study, we describe the technique and review outcomes of our institution's initial 6-year experience. Methods: An institutional database query identified 278 consecutive patients who underwent Ivor Lewis esophagogastrectomy using an STS esophagogastric anastomotic technique from 2009 through 2015. A retrospective review was conducted to assess outcomes with a focus on anastomotic complications. Results: There were a total of 8 (2.9%) anastomotic leaks in patients who underwent STS esophagogastric anastomosis, 3 of which were grade I/II leaks and required no intervention. There was a leak rate of 6.3% (2 of 32) after esophagectomy for benign conditions (both leaks occurring in 8 total patients (25%) who received surgery for end-stage achalasia) compared with a 2.4% leak rate (6 of 246) in whom esophagectomy was performed for malignancy (P =.22). Fourteen patients (5.0%) required a median of 2 dilatations for anastomotic stricture after STS anastomosis. Supplemental jejunostomy feedings were required in only 11.1% of these patients after hospital discharge. Conclusions: We believe this novel STS technique provides excellent results with respect to the incidence of intrathoracic esophagogastric anastomotic leak and stricture after esophagectomy. Additionally this technique has significantly reduced the need for enteral feeding after hospital discharge.