Patients who have undergone bariatric surgery and present with upper abdominal symptoms pose a diagnostic and management challenge. This is a case report of a 53-year-old lady who presented a number of years after vertical banded gastroplasty with upper abdominal pain and weight gain. Radiological investigation demonstrated a large para-esophageal hernia including the stapled area of the stomach, but with a staple-line dehiscence. She successfully underwent repair of the hiatus hernia and conversion to a Roux-en-Y gastric bypass resulting in resolution of the abdominal pain and weight loss.