Raeder syndrome (paratrigeminal oculosympathetic syndrome) is a rare clinical entity characterized by ipsilateral trigeminal sensory deficits, ptosis, and miosis, with an absence of anhidrosis secondary to interruption of the postganglionic oculosympathetic pathway. Going back to its original description, this constellation of physical examination findings has historically been associated with intracranial pathology involving the middle cranial fossa. Understanding this pathway is important in distinguishing Raeder syndrome from Horner syndrome, as the presentation of the former is now recognized to accompany a number of other disease entities in the head and neck region. We present an unusual case of Raeder syndrome associated with bacterial sinusitis, and we discuss its management and review the literature.