Retrograde jejunal intussusception is a rare complication following gastric surgery. Unless this complication is suspected, diagnosis is very difficult. Early diagnosis is very important in preventing avoidable morbidity and mortality. Awareness of this rare complication would help in early diagnosis and appropriate management. We present a case of an 84-year-old woman who visited the emergency department with hematemesis. Endoscopy and a computed tomography scan revealed a retrograde jejunojejunal intussusception, which was treated by surgical manual reduction.