Plummer Vinson Syndrome (PVS) is characterized by the triad of dysphagia, iron deficiency anemia and upper esophageal webs. The pathophysiology of this condition is not clear, but ultimately the correction of the iron deficiency anemia leads to resolution of the webs, and endoscopic dilation can alleviate web-related dysphagia. Here, we present a case in which the patient presented with symptoms associated with anemia without initial complaint of dysphagia. This case illustrates the importance of monitoring for concurrent disease when working up anemia. A 55 year-old woman with medical history significant for 40 pack years of smoking and without age appropriate cancer screening presented with a 3 day history of dyspnea and orthopnea. Review of systems was significant for dysphagia to pills, but patient denied dysphagia to solids and liquids. She also reported a 1-year history of fatigue and weight loss she attributed to decreased appetite. Physical exam was significant for glossitis and koilonychia. Admission labs were significant for a hemoglobin 6.7 g/dL, MCV 60.9, iron 7 mcg/dL (normal range 40-150 mcg/dL), ferritin < 5, TIBC of 435 mcg/dL (normal range 250-400) corrected retic 0.6% and a positive fecal occult blood test. Esophagogastroduodenoscopy (EGD) revealed moderately stenotic cricopharyngeal webs consistent with a diagnosis of Plummer Vinson Syndrome. With intubation using the standard upper endoscope, these webs were dilated successfully. Colonoscopy was significant for resection of two polyps and internal hemorrhoids. She was discharged with iron 325mg PO BID. Six months later, she no longer reported dysphagia to pills, had a 10 pound weight gain, hemoglobin of 12.8 g/dL and MCV 84. The pathophysiology of this condition is not clear, but ultimately the correction of the iron deficiency anemia leads to resolution of the webs and endoscopic dilation can alleviate web-related dysphagia. Due to improvement in nutritional status, advancement in medical technology, and increased awareness about iron deficiency anemia, this syndrome is rare in the 21st century. This patient was at high risk due to very limited interactions with health care providers. PVS is important to recognize, and these patient deserve close follow up, because for unclear reasons, affected patients have an increased risk of esophageal or pharyngeal squamous cell carcinoma.