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Hiatal herniations are most commonly diagnosed during work-up for gastroesophageal reflux disease. Here, we present a patient with retrosternal pain for whom the computed tomography scan showed a lipomatous formation in the lower posterior mediastinum, and further examination indicated the origin to be paraesophageal herniation (PEH) of the greater omentum. This was confirmed by laparoscopy, the herniated part of the greater omentum was repositioned and the hiatal hernia was repaired. During recovery the patient complained of dysphagia, a common and transient postoperative occurrence, but which later proved to be a mechanical obstruction caused by a bolus. This case raises awareness of potential differential diagnoses pre- and postoperatively in conjunction with PEH, and the management of such differential diagnoses is discussed.