Introduction. Pancreatic pseudocysts are a common complication of acute pancreatitis. Pancreatic pseudocyst's natural history ranges between its spontaneous regression and the settlement of serious complications if untreated, such as splenic complications, hemorrhage, infection, biliary complications, portal hypertension, and rupture. The rupture of a pancreatic pseudocyst to the peritoneal cavity is a dangerous complication leading to severe peritonitis and septic conditions. It requires emergent surgical exploration that is often of great technical difficulty and with important morbidity and mortality. Case Study. We present two cases of spontaneous rupture of pancreatic pseudocysts, managed differently according to the local and systemic conditions. Conclusion. The best surgical choice is the internal drainage of the cyst to the GI tract; however, in some conditions, the external drainage is the only choice available.