Acquired Tracheoesophageal Fistula (TEF) is a life threatening condition and usually occurs secondary to trauma or invasion of anatomic structures in the mediastinum by neoplasm. It is uncommon for infants to ingest articles large enough to produce esophageal damage. Failure to diagnose foreign body ingestion in a timely manner can allow time for erosion into the wall of the esophagus with subsequent profound injury to the esophagus, the trachea or both. We present a case of plastic lollipop ring ingestion in a 10-month-old infant resulting in acquired TEF. The importance of communication between the surgeons and the anesthesiologists prior to definitive operative procedure as well as during repair of a traumatic injury to the trachea is stressed. Acquired TEF in an infant can be a life threatening emergency and the anatomic relationships and plans for the worst-case scenario should be reviewed prior to taking the infant to the operating room.