Intracorporeal esophagogastrostomy after laparoscopic proximal gastrectomy is technically challenging. We employed a computer-mediated flexible circular stapler (SurgASSIST) for esophagogastrostomy in 2 cases with gastrointestinal stromal tumor located near the esophagogastric junction. Esophagogastrostomy was successfully constructed intracorporeally using the double-stapling technique. Operation times for the 2 cases were 225 and 170 minutes. No anastomotic leakage was encountered. However, anastomotic stricture requiring balloon dilatation occurred in 1 patient. The SurgASSIST system was feasible for esophageal anastomosis in laparoscopic proximal gastrectomy. However, the digital loading unit (DLU) is too large to introduce transorally, and attempting introduction of the DLU through the narrow lumen may create lesions or perforate the organ. Further improvements in the DLU will facilitate wider use of this system for various procedures in laparoscopic surgery.