Intussusception following Roux-en-Y gastric bypass is a rare, potentially life-threatening complication. Patients present with intermittent obstructive symptoms, and the diagnosis is made on imaging. Treatment is surgical considering the high likelihood of non-operative failure, strangulation, incarceration, perforation and concern for malignancy. We present the case of a woman in her 60s with a history of Roux-en-Y gastric bypass who presented with retrograde jejunojejunal intussusception at the distal Roux anastomosis. She proceeded to the operating room for complete anastomotic resection with reconstruction of three blind ends via two sequential isoperistaltic anastomoses. She progressed appropriately throughout her hospitalisation and was discharged on postoperative day 5 without recurrence. While intussusception in Roux-en-Y anatomy has been previously described, a literature review yielded sparse results in detailing its surgical correction. We highlight our unique surgical approach of jejunojejunal anastomotic resection with the creation of sequential isoperistaltic side-to-side anastomoses.