Small bowel obstruction (SBO) secondary to intussusception of Meckel’s diverticulum (MD) is a rare cause of acute abdominal pain that may warrant urgent surgical treatment. Volvulus or intussusception of the small bowel with presence of MD as the lead point is the most commonly reported etiology of Meckel’s related obstructions. We report an interesting case of a small bowel obstruction caused by the intussusception of an MD within its own lumen. The case involves a 30-year-old male who presented to the emergency room with acute, severe abdominal pain with an abdominal computed tomography (CT) showing a distal high-grade SBO. Decision was made to take the patient to the operating room urgently due to his clinical examination and radiologic imaging, specifically CT scan. Diagnostic laparoscopy was performed and subsequently converted to an exploratory laparotomy, which revealed the intussuscepted MD with focal necrosis into the distal small bowel causing an SBO. A segmental small bowel resection with hand sewn primary anastomosis was performed. The case presents an interesting challenge in deciding when to take a patient with an SBO to the operating room versus initial conservative management and what the treatment should be if an MD is encountered. In addition, the case emphasizes the importance of history and physical exam findings in coordination with radiologic imaging in helping to make appropriate decisions in a timely manner for operative vs conservative management of an SBO. It reminds us that, Meckel’s diverticulum, although less commonly the cause of a small bowel obstruction in the adult population, needs to be on the differential diagnosis and we need to have a high clinical suspicion for this possibility to ensure appropriate treatment in a timely manner.