Post-esophagectomy hiatal hernia is a rare complication having varied presentation from asymptomatic cases detected incidentally on follow-up imaging to acute surgical emergency for strangulation or gangrene. Patients presenting as a surgical emergency have a prolonged post-operative course with significant morbidity. We present three cases of post-esophagectomy hiatal hernia. Two of the three cases were operated for esophageal squamous cell carcinoma (SCC) and one patient was operated for esophageal leiomyomatosis. Two of the three cases (SCC and esophageal leiomyomatosis) underwent minimally invasive Mckeown's esophagectomy and one case underwent robotic transthoracic Ivor-Lewis esophagectomy. All cases underwent contrast enhanced CT (CECT) and were biopsy proven prior to their index surgery. Both cases of SCC had prior neoadjuvant chemoradiation followed by surgery while esophageal leiomyomatosis underwent upfront surgery. All three cases have improved symptomatically and are doing well on follow up (case 1 - 12 months, cases 2 and 3 - 3 months). All three of our cases have different clinical presentation in terms of symptoms, severity, and time duration from index surgery. Two of the three cases underwent emergency surgery and one case which was asymptomatic detected incidentally on surveillance imaging and was managed conservatively. Post-esophagectomy hiatal hernia is a rare entity with varying presentation. The management options in such cases vary depending on the severity of symptoms and time after index surgery. In cases presenting as surgical emergency, successful management depends on prompt detection, early surgery, proper post-operative care, and rehabilitation.