In the past, conservative bypass surgery was usually performed for palliation of malignant obstruction of the gastrointestinal tract. However, endoscopic stenting was developed recently, and technical advances and clinical experience have made it possible to establish stent implantation as one of the main treatment options. There are several advantages in stent implantation over bypass surgery, such as high feasibility and technical success rate, non-invasiveness, rapid symptomatic response, short hospitalization, and cost-effect benefits. Complications, such as stent ingrowth, stent injury by bile or acid, and migration, may occur and early re-insertion is frequently needed. Recently, diverse novel stents which are powered to predict stent migration or ingrowth have been developed and are being used in the clinical setting. In general, stent implantation is known to be beneficial in patients who are expected to survive <6 months, and surgical bypass may be more effective in patients who can survive >6 months. In this review, we have compared the technical feasibility, clinical outcomes, complications, and cost-benefit between stent implantation and bypass surgery, and determined the optimal treatment strategy in malignant upper gastrointestinal obstruction.