Gastrointestinal leakage is one of the most serious post surgical complications and is a major source of mortality and morbidity. The insertion of a covered self-expandable metal stent could be a treatment option in selected cases. However, it is unclear how long the stent should be retained to achieve complete sealing, and membrane-covered stents have the problem of a high migration rate. We observed four cases of postsurgical leakage following the primary closure of a duodenal perforation, esophagojejunostomy, and esophagogastrostomy, each of which was successfully managed by the temporary placement of covered stents. In all cases, the optimal time of stent removal could be estimated by the markedly decreased amount of drainage, the lack of leakage observed on radiocontrast images, and the endoscopic findings. In this case series, all of the stents could be removed within 7 weeks. For those cases with a high risk of migration, stents with temporary fixations to earlobes and/or partially uncovered proximal flanges were used. These results suggest that the application of a covered stent could be a treatment option for various gastrointestinal leaks after surgery, particularly when the defect cannot be sealed by conservative care and the leakage has good external drainage.