Plummer-Vinson syndrome (PVS) is a rare condition marked by postcricoid dysphagia, upper esophageal webs, and iron deficiency anemia. It has been associated with increased risk of hypopharyngeal and esophageal malignancies, necessitating early diagnosis. This case series reviews four patients who presented to Adera Medical and Surgical Center in Addis Ababa, Ethiopia, with PVS. All patients exhibited progressive dysphagia, anemia, and fatigue. Endoscopic evaluation revealed esophageal webs in the upper esophagus, and treatment included iron replacement therapy and esophageal dilation as needed. Hemoglobin levels improved in all cases, with three patients experiencing complete resolution of dysphagia, while one required a repeat dilation after 6 months for recurrence.