The diagnosis of gastric volvulus can be a clinical challenge as it is rare, and the symptoms are often nonspecific and intermittent. Upper endoscopy is a minimally invasive intervention that may be repeated more than once to provide key information and ultimately establish such a diagnosis. To emphasize the role of upper endoscopy in surgical cases with recurrent upper gastrointestinal obstructions, we present a case of intermittent gastric volvulus in a patient with a remote history of complex chest wall reconstruction for invasive breast cancer using an omental flap. She presented with substernal chest pain, belching, nausea, and vomiting. Although the initial imaging suggested duodenal obstruction, exploratory laparotomy and intraoperative upper endoscopy did not show any pathology in the stomach or duodenum. Repeat upper endoscopy due to recurrence of obstructive symptoms shortly after the initial exploratory laparotomy revealed a gastric volvulus. This resulted in abnormal duodenal orientation which caused intermittent duodenal obstruction while the pathology was in the stomach. Gastric volvulus may be spontaneously reducible, leading to discordance in findings during the clinical course. This could explain the absence of visible twisting on initial exploratory laparotomy in this patient and the subsequent findings of volvulus on upper endoscopy. Thus, it is important to consider gastric volvulus as a possible cause of symptoms despite initial negative findings as it is a dynamic process and may only be discovered through relook upper endoscopy and imaging.