Navigating around a large ventral hernia laparoscopically poses unique challenges and requires careful planning, skilled surgical technique, and creative problem-solving.The patient is a 59-year-old woman with insulin-dependent diabetes, hyperlipidemia, hypothyroidism, lupus anticoagulant disorder, a history of non-Hodgkin's lymphoma status post radiation and chemotherapy, and a large, recurrent ventral hernia that had been repaired with a laparoscopic intraperitoneal onlay mesh.A preoperative work-up was performed, including a PET CT given her history of malignancy. Imaging revealed a large, recurrent ventral hernia containing omentum, small bowel, and colon with a fascial defect measuring approximately 13 x 12 cm. Given the size of her ventral hernia and a BMI of 58.2 kg/m², we opted to proceed with a laparoscopic sleeve gastrectomy. Twenty months later at a BMI of 45.8 kg/m², we completed her single anastomosis duodenoileostomy. Optical entry was performed in the left upper quadrant with a 12 mm trocar. Additional 5 mm ports were placed strategically on the patient's left side in order to reduce the hernia contents. A 12 mm port was placed through the fascial defect, and an additional 5 mm port was positioned in the right upper quadrant in order to run the bowel without risking additional injury. A tension-free, end-to-side, hand-sewn duodenoileostomy was then performed with running 3-0 PDS sutures in two layers posteriorly followed by an interrupted 3-0 PDS single layer anteriorly. The patient tolerated the procedure well with no complications and was advanced to a regular diet in the outpatient setting.