Salivary bypass tubes have been used with great success in preventing neck wound contamination from saliva and decreasing the risk of pharyngoesophageal stenosis. However, complications from esophageal tubes and risk factors for these complications should not be overlooked. Complications can be fatal, as demonstrated in this case of esophageal-subclavian artery fistulization. Retroesophageal subclavian artery (RRESA) is 1 of the most common anatomical variations of the aortic system. Typically producing no symptoms, its discovery is usually coincidental. However, under the right circumstances, this artery can form a fistulous tract. This occurrence has also been documented in cases of long-term nasogastric tube placement and incorrect use of "esophageal" stents. This unique case describes a 62-year-old man who suffered an arterioesophageal fistula during use of a Montgomery salivary bypass tube (MSBT)--a frequently used and exceptionally safe management tool in patients with head and neck cancer.