Physiologists Eduard Pfluger and Claude Bernard first introduced one lung ventilation (OLV) in 1871. Today, it is now a frequently used technique in open or minimally invasive cardiothoracic surgeries. One key benefit of the use of OLV is improved surgical exposure. Historically, lung isolation catheters used under fluoroscopic guidance or a Fogarty catheter were used to achieve OLV. In present times, endobronchial blockers (EBBs) in conjunction with single lumen endotracheal tubes and double lumen endotracheal tubes (DLTs) are used to achieve intraoperative OLV. Some complications of EBBs include mucosal injury, bleeding, bronchial rupture, pneumothorax, malpositioning-induced respiratory arrest, severe hypoxemia, and dislodgement. The incidence of iatrogenic tracheal rupture with single lumen endotracheal intubation is reported to be approximately 0.005%, and with double lumen ETT, the incidence may be between 0.05 and 0.19%. Mortality associated with tracheal rupture with DLTs is approximately 8.8%. Data on airway injury with endobronchial blockers is limited, and reported cases of bronchial perforations with use of EBBs are rare suggesting that EBBs may be the safer option for OLV. In this case report, we will be discussing a case of iatrogenic endobronchial rupture following endobronchial blocker placement.