Radiological imaging plays an essential role in the diagnostic algorithm of tracheoesophageal fistula (TEF) in the prenatal and postnatal period. Although the primary imaging modality is esophagogram with water-soluble contrast, there are various imaging techniques to make the diagnosis. As ultrasound and magnetic resonance imaging (MRI) are compatible during the prenatal period, computed tomography (CT) and plain radiographs may provide additional information to contrast studies in the postpartum period. Imaging is also crucial to identify other associated anomalies and to predict the outcome. Moreover, radiological examinations are often necessary in the postoperative period to define complications and recurrent TEF. The aim of this article is two folds; first to describe indications, imaging methods and findings of congenital, acquired, and recurrent TEF and accompanying conditions to confirm the diagnosis, and second, to discuss the yield of different imaging methods in line with the literature. While describing congenital TEF, concomitant anomalies, such as esophageal atresia (EA) and tracheal agenesis were depicted systematically according to the prevalent classifications. Among acquired TEF; two specific etiologies [iatrogenic and button battery (BB) ingestion] were explained more detailed, since these entities are diagnostically challenging, required urgent management, and may have serious consequences. We also would like to emphasize pearls and challenges of the diagnostic modalities.