Abstract Background Hiatal hernia post esophagectomy is a delayed postoperative complication. Historically, in open surgery, the incidence is rare. The increased utilization of minimally invasive methods has increased the incidence of hiatal hernias. Current literature is limited to case series. There is even less on frequency and management of re-recurrent cases. Our objectives were to identify the incidence of hiatal hernia post esophagectomy and the outcomes of the recurrent cases. Methods A retrospective analysis of prospective data at a single center was conducted on esophagectomies performed 2017 to 2022. Non-gastric conduit reconstructions were excluded. Baseline patient demographics including comorbidities, type of tumor, neoadjuvant therapy, surgical approach (open versus minimally invasive [MIE]), and conduit construction were recorded. Radiographic presence of non-gastric conduit abdominal contents was defined as hiatal hernia. Time of hiatal hernia occurrence, details of the repair and timing re-recurrence was recorded. Associated factors described in literature including baseline demographics, neoadjuvant therapy, operative technique, conduit diameter and use of pexy techniques were analyzed with univariate analysis. P<0.05 was considered significant. Results A total of 565 esophagectomies met inclusion criteria, 78% (439/565) were MIE. Robotic-assisted comprised 33% (143/439) of the MIE cohort. A hiatal hernia was identified in 3% of patients (15/565). All had malignancy and were Ivor Lewis (11/15, 73%) or 3-hole (4/15, 27%). The majority had an MIE (13/15, 86%), one had open esophagectomy (6%), and one had hybrid (1/15, 6%). There was no difference in risk factors between the hernia and non-hernia groups. Median time to hernia was 5 months (IQR: 4, 12). All underwent repair. Recurrent hernia occurred in 33% of patients (5/15), all within the robotic-assisted MIE. Conclusion Hiatal hernia post esophagectomy occurred in 3% of cases, and most cases occurred within the MIE group. Recurrence of hernias occurred in robotic-assisted esophagectomy patients. Analysis of patient-specific factors such as prior hiatal hernia, body-mass index, neoadjuvant therapy, operative technique, conduit pexy technique all did not reveal significant correlation with hiatal hernia development. The recurrence of hiatal hernia all required redo repairs. Though we had no deaths in the hiatal hernia cohort, repeat surgeries affect morbidity in esophagectomy patients. Further analysis is needed to identify ways to minimize hernia recurrence in minimally invasive esophagectomy.