Objective: Although Plummer–Vinson syndrome (PVS) is rare, it is imperative to be aware that this group of patients is at an increased risk of squamous cell carcinoma (SCC) of the pharynx and the esophagus, which can be identified early. The aim of this study was to determine the prevalence of cricopharyngeal webs, iron deficiency anemia (IDA), and dysphagia among individuals diagnosed with PVS in Puducherry. Materials and methods: Over a span of 2 years, a total of 30 patients who were diagnosed with PVS and had presented to the department of ENT at a tertiary care center were included in this single-center study with a review of past events. Dilatation of postcricoid webs was done, followed by a postoperative iron correction. A regular follow-up for 1 year was done to examine the occurrence of cancerous alterations and the reappearance of symptoms. Results: We found the highest incidence (90%) to be in females presenting at the 4th and 5th decades of life, with the most significant presenting complaint in all patients being dysphagia. The majority of them had features of IDA like pallor, koilonychia, glossitis, angular stomatitis, and bald tongue. All patients (100%) showed iron deficiency status in biochemical analysis and postcricoid web in barium swallow. Three patients had associated malignancies, of which two were esophageal and one was hypopharyngeal. Conclusion: Plummer–Vinson syndrome (PVS) is a symptom complex consisting of dysphagia, IDA, and esophageal webs. It is a condition that carries an increased risk for the development of malignancy and has a higher prevalence among people of South Indian descent, especially in the Puducherry region, and comprehensive evaluation should be conducted in these patients to exclude the presence of concomitant malignancy. The esophageal web in PVS can be safely dilated, and the response is sustained during follow-up despite rare recurrences.