Pancreatic pseudocyst is a common complication of acute and chronic pancreatitis. Extension of a pancreatic pseudocyst into the mediastinum is rare. We present a case of a 43-year-old male with a history of pancreatitis, who presented with dysphagia and was found to have a pancreatic pseudocyst. The pseudocyst was extending to the mediastinum and compressing the esophagus. It was successfully drained externally by computed tomography-guided catheter intervention. Depending on the location and size, patients may present with dyspnea, chest pain, palpitations, or dysphagia; sometimes with hemoptysis, acute respiratory compromise, or cardiogenic shock. There are no recommended guidelines for management. Watchful waiting for spontaneous regression, medical therapy, or drainage internally or externally with endoscopic, percutaneous, or open surgical approach are available options. Based on our own experience and literature review of such cases, we present a management strategy that can limit both complications and recurrence rate. This case emphasizes the importance of the possibility of mediastinal extension of a pancreatic pseudocyst and provides reference guidelines to approach the same.