Herniation of abdominal contents through the diaphragm into the thoracic cavity can occur after blunt abdominal injury, resulting in a permanently acquired diaphragmatic hernia. Their clinical presentation is varied and non-specific, which can go unnoticed for a long duration.A 27-year-old male presented with right upper quadrant pain and right-sided pleuritic chest pain for the past 20 days. His past medical history included high-impact blunt trauma a few years back. His workup revealed a right-sided diaphragmatic hernia through which the gallbladder had herniated into the thoracic cavity, along with liver and hepatic flexure of the colon. The gallbladder contained gallstones which were the cause of his symptoms. The patient was managed successfully with a laparotomy and repair of the diaphragmatic hernia and cholecystectomy.After blunt abdominal trauma, right-sided diaphragmatic injury is less common because most of the trauma is absorbed by the liver, providing a protective effect. The sign and symptoms of acquired diaphragmatic hernia lack sensitivity and specificity, due to which many cases remain undiagnosed and are incidentally picked up on chest auscultation where bowel sounds are audible in the chest, and breath sounds on the affected side are absent, whereas patients have complaints of respiratory difficulty and recurrent pneumonia. Chest and abdominal imagining in the form of chest X-rays and abdominal ultrasound can help diagnose.The case we present was a unique presentation of acquired right-sided diaphragmatic hernia resulting in herniation of the gallbladder in the right-sided chest and leading to acute cholecystitis. The treatment modality is surgical repair of the diaphragm. Any patient presenting with unusual symptoms of pneumonia or abdominal pain should be investigated, especially patients with a history of blunt abdominal trauma.