Laryngomalacia is the most common cause of neonatal stridor, accounting for up to 60% of cases . Less common causes of neonatal stridor include subglottic or tracheal stenosis, or congenital masses of the upper airway. Neonates with an identified congenital etiology of symptomatic upper airway obstruction often have synchronous airway lesions leading to multilevel airway obstruction. These infants deserve an endoscopic evaluation to better diagnose and manage respiratory distress. Here we present a rare case of an infant initially diagnosed with croup, but ultimately found to have multilevel airway obstruction including severe laryngomalacia and an obstructing tongue base mass.