Standard double-lumen tubes (DLTs) are unsuitable in patients with end tracheostomy due to the shortened tracheal length and atypical stoma angulation. This case highlights the challenges of achieving one-lung ventilation (OLV) in patients with end tracheostomies due to anatomical changes following total laryngectomy. A 68-year-old male with a history of total pharyngo-laryngo-esophagectomy, gastric pull-up, and end tracheostomy underwent video-assisted thoracic surgery (VATS) for left lung wedge resection and lymph node dissection. A #7.5 Portex cuffed tracheostomy tube and a Coopdech bronchial blocker (BB) were used to achieve OLV. The Coopdech BB was placed intraluminally through the tracheostomy tube into the left main bronchus, and the lung isolation was confirmed clinically via auscultation and subsequently with the guidance of fiberoptic bronchoscopy. BBs are often preferred for their flexibility and ability to accommodate tracheostomy anatomy while minimizing stoma trauma. This approach provided stable lung isolation and accommodated anatomical variations. The case underscores the importance of tailoring OLV strategies to patient-specific anatomical challenges in patients with end tracheostomy.