Long-term (>30 days) esophageal stenting is controversial. Previous studies have documented complications associated with long-term esophageal stent use. This study's objective was to investigate complications associated with long-term esophageal stent use. A retrospective review of stenting done by thoracic surgery for any reason between 2010-2020 was completed. Patients were included if they had at least 30 days of follow-up after their initial stent placement. Outcomes included stent dwell time, patient outcomes, procedural and stent-related complications. Fifty-six patients, with 25 having ≥2 stents placed were included; overall, 90 stents were placed. The median length of initial esophageal stent dwell time was 59 [interquartile range (IQR), 21-119] days. Stent migration was the most common complication and occurred more with benign indications (P=0.12). As the length of dwell time increased, prevalence of any complication decreased. Complication rates between short-term (<30 days) and long-term stents were not significantly different (P=0.39). No instances of esophageal perforation or aortoesophageal fistulas related to stents were identified. There was one instance of post-esophagectomy tracheoesophageal fistula which was managed successfully with prolonged stenting. Over a 10-year period, there were no instances of stent erosion into the aorta or esophageal perforation, and the most frequent stent-related complication was stent migration. Long-term esophageal stenting did not result in increased rates of stent related complications in our cohort. This case series demonstrates that long-term stents may be safely used for many different indications. Randomized controlled studies may be needed to validate these findings.