<p>This case report describes an atypical presentation of a bilateral Killian-Jamieson Diverticulum (KJD) in a seventy-year-old woman, characterized by long-standing reflux, indigestion, and a six-months of progressive dysphagia. Initial investigations, including oesophago-gastroduodenoscopy (OGD), revealed the presence of pharyngeal pouches. Subsequent barium swallow and CT imaging confirmed bilateral KJD. Given the risks associated with endoscopic treatment especially in a bilateral case, an external trans-cervical excision of the left pharyngeal pouch with cricopharyngeal myotomy was performed. Postoperative follow-up indicated a successful resolution, and the patient was transitioned to oral intake. Follow up was planned on a six-monthly basis for close monitoring of her swallow function. This case highlights the rarity of bilateral KJD and underscores the importance of considering pharyngeal pouches in patients with persistent dysphagia and dyspepsia. This report also emphasizes that while endoscopic treatment is mainstay, external surgical approaches are viable for more complex and rare cases.</p>