Congenital tracheobronchial stenosis presents complex challenges in pediatric respiratory care. This study delves into the intricate management of severe upper airway obstruction through a detailed case presentation of Felicity, a 7-month-old infant with congenital tracheobronchial stenosis. Felicity's medical journey commenced with a challenging birth marked by respiratory distress and difficulties in intubation, prompting suspicion of congenital anatomical malformation. Transferred to Al Jalila Hospital and later to Sheikh Khalifa Medical City ICU, she underwent extensive interventions, including tracheoplasty and multiple dilatation procedures, to alleviate airway stenosis. Despite surgical efforts, Felicity remains oxygen-dependent due to chronic respiratory failure and faces recurrent episodes of respiratory distress. She relies on a gastrostomy tube for enteral feeding due to unsafe swallowing secondary to airway obstruction. Diagnostic imaging revealed severe tracheal stenosis, emphasizing the severity and complexity of her condition. The multidisciplinary approach undertaken, involving Pediatric ENT, Pulmonology, Surgery, and nutritional specialists, underscores the collaborative efforts required for managing congenital airway anomalies. This case highlights the ongoing challenges in achieving sustained airway patency and emphasizes the need for continued research and advancements in pediatric respiratory care for optimal outcomes in complex airway anomalies.