Background: Pancreatico-pleural fistula (PPF), a rare complication of pancreatitis, stems from pancreatic duct leakage or pseudocyst rupture. Diagnosis traditionally relies on a triad of pancreatitis history, imaging evidence of pancreatic duct disruption with concurrent pleural effusion, and elevated pleural fluid amylase. While CT has 47-63% sensitivity, MRCP (80%) and ERCP (78%) offer improved visualization and therapeutic potential. Case Reports: Case 1: A 37-year-old male, non-smoker, non-drinker, presented with worsening dyspnea due to left-sided pleural effusion. A 5 mm pancreatico-pleural fistula was found and surgically treated via Roux-en-Y fistulo-jejunostomy, resulting in complete recovery over 5 years. Case 2: A 35-year-old male, chronic smoker and drinker, experienced right-sided chest pain and pleural effusion due to chronic calcific pancreatitis. Frey's procedure, drainage, and fistula division led to symptom resolution, sustained over 4 years. Conclusion: PPF diagnosis combines clinical history, imaging, and pleural fluid analysis. While CT remains useful, MRCP and ERCP provide better sensitivity. Management entails initial conservative approaches, including octreotide infusion, followed by surgery if needed. These cases highlight the importance of early recognition and multidisciplinary care for successful PPF management.