Ivor-Lewis esophagectomy is followed by a considerable anastomotic leakage rate, which is a potentially fatal complication, followed by increased morbidity and mortality. The emergence of minimally invasive surgery led to a wide variety of anastomotic techniques, three of which are mainly preferred. Hand-sewn anastomoses can be performed in an end-to-end or end-to-side manner, while stapled end-to-end or end-to-side anastomoses are conducted either as circular-stapled anastomoses using a transorally inserted anvil (Orvil™) or as hand-sewn purse-string stapled anastomoses. In addition, side-to-side esophagogastrostomy with a linear stapler is presented as a promising technique. Hybrid techniques are also reported. No consensus has been achieved upon optimal technique and the decision relies on surgeon preference and skills, cost, and length of the available conduit. Furthermore, numerous techniques have been proposed to prevent anastomotic leakage (AL), including appropriate submucosa apposition, omentoplasty of the anastomosis, wide gastric and duodenal mobilization, sufficient esophageal hiatus enlargement, gentle conduit manipulation, reinforcement of staple line, intraoperative fluorescence angiography, as well as preoperative ligation of the left gastric artery. This chapter aims to provide a critical appraisal of the various anastomotic techniques and the tips and tricks described for reducing the anastomotic leak rate during minimally invasive Ivor-Lewis esophagectomy.