Pneumocephalus is a rare presentation of sinusitis. The purpose of this case series and literature review is to highlight the critical importance of recognizing pneumocephalus on initial brain imaging, since it may serve as the first sign of acute sinusitis with intracranial complication. Although sinusitis is a treatable condition with appropriate and timely antibiotic therapy, failure to recognize intracranial extension and delays to prompt surgical drainage could lead to a dire clinical course.