Chyle leaks are a rare but potentially fatal complication of head and neck surgery carrying an incidence as high as 8.3%. The development of a chyle leak carries significant morbidity ranging from delayed wound healing to oropharyngeal fistulas. Presented here is a case of a chyle leak that developed following a left posterolateral neck dissection that was successfully managed with a combination of drain suction, pressure dressing, and a fatrestricted diet. However, the patient’s course was complicated by repeated chyle leak recurrences that may have been associated with the initiation of medium-chain triglyceride supplementation. Although further research is required to establish a causal relationship, these findings support the concerns of other investigators about the possible counterproductive role of medium-chain triglyceride supplementation in the management of chyle leaks.