Esophageal stricture is a result of luminal narrowing due to inflammation, fibrosis, or neoplasia, and can be classified as benign or malignant. Clinical presentation usually involves symptoms of food impaction, dysphagia, chest pain, and weight loss. Clinical history is critical to ascertain cause of structuring, peptic stricture is the most common benign cause. In this case we highlight a patient with a history of caustic ingestion presenting with reflux-like symptoms and dysphagia, who continued to have persistent symptoms. He had undergone the appropriate work up, with EGD and upper GI contrast study. Despite undergoing prior dilations and stents, his symptoms persisted as he essentially had a nondilatable benign stricture due to fibrosis from his caustic injury. In this case, we demonstrate an attempted transhiatal esophagectomy, which was converted to a minimally invasive Ivor Lewis esophagectomy after the dissection from the abdominal approach became challenging. Furthermore, we highlight the utility of ICG in tracing the gastroepiploic artery in creation of the gastric conduit, and in assessing the anastomosis after pulling the conduit into the chest.