One of the leading reasons for emergency department visits happens to be chest pain and shortness of breath with estimated 6.3 million visits for chest pain and 3 million visits for shortness of breath. Over the years, there has been an upward trend in these demographics. The primary workup is usually toward cardio pulmonary causes. Paraesophageal hernia is a term to describe the herniation of gastroesophageal junction and the gastric fundus through the paraesophageal membrane. Paraesophageal hernias account for 5% of all the hiatal hernias, and patients are usually asymptomatic or have complaints of gastroesophageal reflux. However, on rare occasions, they are notorious to develop complications such as incarceration, gangrene, obstruction of intrathoracic stomach, collapse of the lung, and even death. We take this opportunity to present a 49-year-old man who presented with shortness of breath and chest pain. The initial workup revealed a pulmonary embolism on a computerized tomography scan. However, with better clinical judgment and more imaging, he was diagnosed with a paraesophageal hernia with gastric obstruction and early strangulation causing his symptoms.