Hemangiomas in the head and neck region, especially those that may impact the airway, require special attention perioperatively because of the potential for difficulties with airway management and bleeding control. This case report describes the management of a 31-year-old male with a large hemangioma of the tongue and pharynx undergoing surgical extraction of mandibular third molars under intubated general anesthesia. Despite taking precautions and avoiding traumatizing the hemangioma while securing the airway, massive bleeding occurred during the surgical extractions, which prompted emergent transfer for angiographic embolization and a stay in the intensive care unit until extubation. This case report highlights the additional attention needed for patients with hemangiomas within the oral cavity and upper airway because of the potential for unexpected massive bleeding that can affect airway management and cardiovascular stability.