SUMMARY The circular mechanical and hand-sewn intrathoracic anastomosis are most often used in robot-assisted minimally invasive esophagectomy (RAMIE). The aim of this study was to describe the technical details of both techniques that were pioneered in two high volume centers for RAMIE. A prospectively maintained database was used to identify patients with esophageal cancer who underwent RAMIE with intrathoracic anastomosis. The primary outcome was anastomotic leakage, which was analyzed using a moving average curve. For the hand-sewn anastomosis, video recordings were reviewed to evaluate number of sutures and distances between the anastomosis and the longitudinal staple line or gastric conduit tip. Between 2016 and 2019, a total of 68 patients with a hand-sewn anastomosis and 60 patients with a circular-stapled anastomosis were included in the study. For the hand-sewn anastomosis, the moving average curve for anastomotic leakage (including grade 1–3) started at a rate of 40% (cases 1–10) and ended at 10% (cases 59–68). For the circular-stapled anastomosis, the moving average started at 10% (cases 1–10) and ended at 20% (cases 51–60). This study showed the technical details and refinements that were applied in developing two different anastomotic techniques for RAMIE. Results markedly improved during the period of development with specific changes in technique for the hand-sewn anastomosis. The circular-stapled anastomosis showed a more stable rate of performance.