Abstract: Dermoid cysts are benign congenital subcutaneous lesions. Although complications are exceedingly rare, posterior fossa masses and infections are possible presentations. The clinical and radiological diagnosis is often challenging. We therefore report 2 recent cases treated at our institution. A 4-year-old girl presented with irritability, headache, and vomiting. Magnetic resonance imaging of the head showed an infected occipital dermoid cyst with an associated transosseous dermal sinus tract and an adjacent intraparenchymal abscess. She underwent successful surgical resection and treatment with intravenous antibiotics. A 2-year-old girl presented with a 10-day history of daily fevers, vomiting, and abdominal pain. After admission, she had a complex partial seizure. Magnetic resonance imaging of the head showed an occipital dermoid cyst with a transosseous dermal sinus tract as well as a left occipital abscess. She underwent complete surgical resection and was discharged on a 6-week course of intravenous cefepime, vancomycin, and metronidazole.