INTRODUCTION: Dysphagia amongst the elderly results from increasing dysfunction of the upper esophageal sphincter (UES), which is vulnerable to effects of aging. Prevalence of dysphagia in geriatric population, especially above 80 is higher than overall prevalence in the general population. Zenker's diverticulum (ZD) is the hallmark pathology for UES dysfunction. These false diverticula are herniation of mucosa and submucosa through the Killian's Triangle. Albeit progressive dysphagia is the most common presentation, symptoms can range from globus sensation to obstruction. ZD may rarely present as complete esophageal obstruction. CASE DESCRIPTION/METHODS: An 89 years old female with hypertension, osteoarthritis and polycythemia vera presented with complaint of “having a pill stuck in my throat.” Unable to tolerate her breakfast and spitting up sputum. Similar symptoms in the past for which she changed her diet to soft bread. Initially, it worked however dysphagia gradually worsened to the extent of having to butter her pills to ease swallowing. Denies GERD. Vital signs within normal limits, physical exam revealed enlarged multinodular goiter with retropharyngeal extension however negative Pemberton's sign. Boyce sign was positive on sipping some water. Euthyroid and no other abnormalities. Urgent upper endoscopy was recommended however patient refused but agreed the next day. Endoscopy was remarkable for pill lodged in upper esophagus, upper esophageal ring and impacted food in ZD compressing esophagus. The ring was split using the endoscope and pill pushed down which was then propelled by peristalsis to the stomach. Content of ZD was retrieved with Roth net. Remaining endoscopy exam was unremarkable. ENT evaluation was recommended for ZD and goiter however patient declined intervention. DISCUSSION: ZD often presents as solid food and pill dysphagia, rarely as acute esophageal obstruction as seen in this case. A number of factors in addition to external esophageal compression by the enlarging ZD likely contributed to her presentation, including pressure from enlarged thyroid. ZD compounds the pharyngeal weakness that leads to its development, trapping the patient in a vicious cycle of worsening dysphagia that eventually results in obstruction. Furthermore, an association between esophageal webs and ZD has been demonstrated. Combination of these factors resulted in the complete obstruction in our patient. Dysphagia in old age, always have ZD in mind.