Hiatal hernias occur when intra-abdominal contents protrude into the diaphragmatic opening. Of the four classifications, Type 4 hiatal hernias are the most rare and severe. They develop from herniation of the gastroesophageal junction and abdominal viscera other than the stomach into the thoracic cavity. The resulting increase in intrathoracic pressure can cause a wide variety of symptoms on presentation and potentially lead to misdiagnosis. We present a rare case in which a 78-year-old woman presented with nonspecific symptoms and was diagnosed with incarcerated Type 4 hiatal hernia with sigmoid volvulus. We also report a literature review from 2015 to emphasize the importance of recognizing diverse symptomatic presentations in complex Type 4 hiatal hernias and the need for a comprehensive evaluation, as early detection and prompt intervention are essential in preventing life-threatening complications.