Congenital anomalies causing airway obstruction in the newborn are potentially fatal. However if an effective airway can be maintained the long-term prognosis is often excellent. We present four cases of airway obstruction, three of which were diagnosed antenatally. We discuss the role of antenatal imaging and review delivery options including the need for a multidisciplinary team approach. In conclusion, we recommend antenatal imaging with both ultrasound scan and magnetic resonance to inform perinatal management. Polyhydramnios, in association with suspected neonatal airway obstruction, should alert clinicians to a high-risk situation. We recognize that even in skilled hands, securing an airway can be very difficult and alternatives such as maintenance of the fetomaternal circulation or extra-corporeal life support should be considered.