Jejunogastric intussusception (JGI) is a rare but potentially lethal complication following gastrectomy or gastrojejunostomy surgeries. Diagnosis of this condition can be challenging due to its rarity and non-specific symptoms. This article presents a case report of a 60-year-old male with a history of trans mesocolic gastrojejunostomy who developed acute symptoms of JGI. The patient presented with acute epigastric pain, vomiting, and hematemesis. Physical examination and laboratory tests indicated dehydration, tachycardia, and leukocytosis. Computed tomography (CT) revealed intussuscepted loops within the stomach. Emergency laparotomy was performed, and the intussusception was manually reduced without the need for resection. The patient recovered well and was discharged five days post-surgery. Retrograde jejunogastric intussusception is a rare complication, often occurring years after gastric surgery. It can be classified into acute and chronic forms, with the former presenting with intense pain and potential hematemesis. The condition can arise in different surgical contexts and even spontaneously. The cause of JGI remains unclear, but factors such as hyperacidity, abnormal motility, and increased intra-abdominal pressure have been implicated. Diagnosis can be made through endoscopy or alternative imaging modalities such as CT. Surgical intervention is the treatment of choice, with various options available based on intraoperative findings. Retrograde jejunogastric intussusception is challenging to diagnose and treat due to its rarity and lack of understanding of its causes. Imaging techniques and endoscopy play important roles in diagnosis, while surgery remains the primary treatment option. Vigilance is necessary among medical professionals to consider JGI in cases of acute abdominal pain and vomiting following gastric surgery, allowing for prompt diagnosis and intervention to prevent bowel necrosis. Further research is needed to establish optimal surgical strategies and evaluate recurrence rates.