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Tracheo-oesophageal fistula with oesophageal atresia is common life-threatening congenital malformations with an incidence of 1 in 3500 to 1 in 4500 births. ‘H’ type tracheo-oesophageal fistula is an isolated type with an incidence of 4–5% and least association with congenital anomalies. Its diagnosis is often delayed .We report two cases, one presented as a 3 months female child with ‘nasal regurgitation of feeds, recurrent pneumonia and choking on feeding since 15 days of life, while the other immediately after birth with classic triad of symptoms. A review of the literature is presented, with a focused discussion of presentation and treatment options. Confirmation of diagnosis was done by compiling clinical presentation, high index of suspicion and rigid tracheobronchoscopy findings. Management involved surgery by right transcervical approach. High index of clinical suspicion and early diagnosis can provide a better prognosis.