A 55-year-old woman presented with features of gastric outlet obstruction not responding to conservative treatment at a peripheral hospital. She had gastric surgery 15 years before. On examination, there was a globular mass palpable in the epigastrium. Ultrasound and endoscopy findings were suggestive of retrograde jejunogastric intussusception. After initial resuscitation, emergency laparotomy was undertaken which revealed a jejunogastric intussusception at the previous retrocolic gastrojejunostomy site. After manual reduction of the intussuscepted loop by gentle traction, another segment of the jejunum was seen to be telescoping within this loop. On reduction, this jejunal loop was seen to measure around 20 cm and the apex of the intussusceptum was found to be gangrenous and perforated. Resection of the involved segment was done followed by a Roux-en-y anastomosis to restore the continuity.