We present the case of an 86-year-old patient admitted with what was initially perceived as haemoptysis with coughing of large clots.  Patient had a significant history of comorbidities including atrial fibrillation on Apixaban. Initial assessment by ENT and a CTPA could not explain the symptomatology and the patient underwent an upper GI investigation. On gastroscopy a large, ulcerated area located at 20cm with a bleeding vessel and multiple clots prevented further insertion. Endoscopic dual haemostasis was achieved (3 hemoclips and adrenaline solution). Patient was stabilized with no further bleeding. On second look endoscopy a large (>10cm) oesophageal pouch proved to be the underlying culprit. There was a large ulcer running at the base of the pouch, where now all bleeding stigmata had disappeared. Entrance into the upper oesophageal sphincter proved to be tricky. Histology showed sections of acutely inflamed and ulcerated oesophageal squamous mucosa with focal fungal hyphae and foreign material. No intestinal metaplasia, dysplasia or malignancy was seen in the tissue examined.  The most common complications of Zenker's diverticulum are aspiration pneumonia, and oesophageal obstruction / dysphagia and increased risk of development of carcinoma. Bleeding occurs rarely and to our knowledge there are only a handful of cases reported in the literature of endoscopic management. Indwelling food for long periods can induce ulceration due to chronic inflammation and superimposed fungal infection. In elderly patients with atypical presentation, this rare complication should be considered.