Introduction: A diaphragmatic hernia is a condition characterized by herniation of the abdominal content(s) via a defect in the diaphragm. It may be congenital or may be preceded by a history of trauma. Case Series: Here we report two cases whose diaphragmatic hernias were detected on evaluation of a difficult gastroscopy. Both cases were those of young males who presented with non-specific gastrointestinal (GI) symptoms which warranted further evaluation with upper GI endoscopy and imaging. The first patient had a history of abdominal trauma during a road traffic accident. When scope negotiation proved to be difficult, they were both investigated and found to have displacement of the stomach within the mediastinum. Surgery was done followed by uneventful recovery in both patients. Conclusion: Diaphragmatic hernias do not always present in the background of typical settings and may be asymptomatic in many cases. However when any undue resistance is faced during endoscope negotiation, a high degree of clinical suspicion should be kept for any anatomical aberration—either congenital or acquired. This may ensure early detection and prevent life-threatening acute conditions as an acute gastric volvulus.