Cranial dermoid cysts are rare, embryologic tumors containing fat, hair, and other ectodermal elements. They occur most frequently in the posterior fossa and are typically diagnosed as incidental findings on brain imaging done for an unrelated reason. Traumatic rupture of a previously unidentified intracranial dermoid cyst can mimic symptoms of post-concussion syndrome and should be ruled out with magnetic resonance imaging (MRI). Surgical intervention after traumatic rupture may not result in complete symptom control due to the persistence of dermoid cyst debris in the subarachnoid space. Here, we present the clinical scenario and radiological features of a ruptured dermoid cyst due to trauma, highlighting a rare complication of a classically benign lesion.