Urachal carcinoma is a rare and aggressive malignancy arising from the urachal remnant and accounts for less than 1% of all bladder cancers. It is characterized by late presentation and an unpredictable metastatic pattern, most commonly involving the lungs and liver. Tracheo-oesophageal fistula (TEF) is usually associated with primary oesophageal or bronchogenic malignancies, and occurrence secondary to metastatic urachal carcinoma has not been previously reported. We describe a 33-year-old male with metastatic urachal adenocarcinoma who presented with cough and blood-tinged sputum triggered by swallowing liquids. Contrast-enhanced CT of the thorax suggested peri-tracheal pathology, and bronchoscopy confirmed a large fistulous communication in the posterior tracheal wall. The patient was managed with bronchoscopic placement of a self-expandable metallic stent, which resulted in symptomatic improvement. This case illustrates an exceptionally rare presentation of metastatic urachal carcinoma causing malignant TEF and emphasizes early and timely airway intervention to reduce aspiration-related complications and improve quality of life in advanced malignancy.

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