Esophageal intramural pseudodiverticulosis (EIPD) is a rare disorder of the esophagus characterized by the presence of outpouching flask-shaped lesions. These lesions represent false lumens that may be scattered throughout the esophageal wall. We present a rare case of EIPD complicated with esophageal strictures. The case is unique because the small lesions of EIPD remained undiagnosed for many years on prior esophagogastroduodenoscopy examinations until complicated with worsening symptoms of dysphagia due to esophageal stricture. The patient was managed with serial dilations of esophageal stricture. Diagnosing these lesions may be missed in early stages as the lesions are small and may require other radiological modalities to confirm the diagnosis. EIPD lesions itself can be managed conservatively with anti-inflammatory therapy and treatment of underlying risk factors. Those with severe disease and coexisting complications are managed with endoscopic or surgical interventions.