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Laparoscopic adjustable gastric banding was previously a commonly performed bariatric procedure. However, in recent years, the procedure has become less commonly performed. Long-term complications nonetheless persist and continue to be seen in clinical practice. We present a case of an esophago-pleural fistula complicating a longstanding laparoscopic adjustable gastric band in a woman presenting with persistent empyema. Palliative esophageal stenting was successfully performed, and the patient was discharged home on hospice care per her family’s wishes.