A tracheal diverticulum (TD) is a generally benign medical condition, where there is an outpouching of the tracheal wall. Additionally, it is generally asymptomatic but there have been reported cases of adverse outcomes linked to TD. Here we present a case of a tracheal diverticulum that was incidentally found during the workup for stroke in a patient. Moreover, due to its radiologic appearance, there was concern for pneumomediastinum. We highlight the presentation and clinical importance of TD owing to the complications one is predisposed to from having this condition.