Background. With recent advancements in endoscopy, self-expandable metal stents (SEMS) have been used to treat gastrointestinal leaks, perforations, and strictures. Stent migration frequently complicates management and often requires additional treatments to reach resolution. Our study aimed to determine predictive factors for stent migration. Methods. Consecutive procedures involving SEMS placed with and without fixation after upper gastrointestinal surgery between 2009 and 2014 were retrospectively reviewed. Demographic, surgical history, rate of stent migration, and stent characteristic data were collected. Rates of stent migration were compared. Results. We reviewed 214 consecutive procedures involving stents placed in the foregut. Median duration of stent placement was 4.0 ± 10.3 weeks. Forty-three (20%) stents migrated after placement. Of those, 27 (63%) required stent replacement. Eleven (5%) procedures utilized stent fixation and 203 (95%) did not. Fixation techniques included endoscopic clips (9%), endoscopic sutures (73%), and transnasal sutures (18%). Stent migration rate was not different between those with and those without fixation (P = .2). Rate of migration was significantly higher in procedures involving fully covered stents (P < .001). Migration occurred after esophagectomy and gastric bypass (P < .001 and P < .05, respectively) and in patients with diabetes (P < .01). Conclusions. A challenge with SEMS use is stent migration. Diabetes and using fully covered stents were associated with migration as were SEMS used to treat complications of esophagectomy and gastric bypass. Stent fixation was not associated with the prevention of stent migration. No pattern was found that favors an approach to reduce stent migration.