A pancreatic fistula is defined as the leakage of pancreatic fluid into another organ or compartment because of pancreatic duct disruption or pseudocyst formation. It is most often seen in middle-aged men between 40 and 50, particularly in patients who have a history of chronic alcoholism and pancreatitis. The tract may fistulae into the pleura, creating a pancreaticopleural fistula, an exceedingly rare condition presenting as a recurrent pleural effusion and extremely high amylase levels, a key distinguishing factor in diagnosis. Here, we present such a case of a recurrent pancreaticopleural fistula and review the presentation, pathophysiology, diagnosis and treatment.