Plummer-Vinson syndrome (PVS) is a complex condition characterized by a classic triad of dysphagia, iron deficiency anemia (IDA), and an upper esophageal web. Dysphagia represents the most important symptom of PVS and is usually observed with solid food. Therapeutic options for dysphagia include iron supplementation and/or endoscopic balloon dilation based on symptom severity. PVS can be treated easily and regular iron replacement therapy can prevent disease progression. We describe a 63-year-old woman diagnosed with a simple esophageal web, who underwent esophageal dilation 13 years prior to presentation. However, she revisited our center because of dysphagia secondary to an esophageal foreign body, and endoscopy revealed esophageal web relapse. Investigations revealed IDA, and the patient was eventually diagnosed as PVS. She underwent successful endoscopic dilation and denied recurrent dysphagia after continuous intake of iron tablets. We recommend continuous management of IDA, as well as endoscopic dilation and a multidisciplinary therapeutic approach to ensure favorable prognosis in PVS patients.