Traumatic diaphragmatic rupture is a rare condition with clinical stigmata that overlaps with a similarly fatal condition such as tension pneumothorax. Although the former is much rarer, early differentiation between a ruptured diaphragm and a tension pneumothorax is crucial to avoid incorrect interventions. In this case, we present a middle-aged male construction worker who fell from the roof of a two-story building and presented to our emergency department with a clinical presentation similar to that of tension pneumothorax. However, a chest X-ray later revealed a left diaphragmatic hernia, which completely altered the management. This case helps highlight the importance of widening one’s list of differential diagnoses, especially in the setting of a hectic environment and a vague presentation.