<p>Esophageal perforation is a rare but life-threatening condition with a variety of causes, including iatrogenic injury, spontaneous rupture, and trauma. Early and accurate diagnosis is critical due to the condition’s high morbidity and mortality. The evaluation of esophageal trauma relies heavily on imaging, where CT with oral contrast and fluoroscopy are the primary tools for diagnosis and management. The high sensitivity of CT allows radiologists to exclude esophageal perforation when negative and eliminates the need for subsequent and more time and resource intensive fluoroscopic evaluation. Diagnostic challenges increase in the postoperative patient, requiring multimodality imaging evaluation. CT is the preferred initial modality due to its superior sensitivity for detecting extraluminal air, fluid collections, and oral contrast extravasation. Fluoroscopic esophagography is complementary to CT in postoperative cases, as the dynamic nature of fluoroscopy allows differentiation of apparent extraluminal contrast seen on CT depending on whether it stays fixed in location or is freely communicating.</p> Graphical abstract <p></p>