Abdominal pain is one of the most common presenting complaints at the Emergency Department (ED). Given the myriad of possible differential diagnoses for abdominal pain, it becomes more important to diagnose conditions requiring emergent surgical intervention early. We present a case of an elderly male patient with abdominal pain secondary to perforated hollow viscus, subtle evidence of pneumoretroperitoneum on the initial supine abdominal X-ray, and review the signs of pneumoperitoneum and pneumoretroperitoneum on plain abdominal X-rays.