In this article, the authors describe 2 cases of Chiari type I malformation (CM-I) in students presenting to a college health center within a 6-month period. A review of CM-I, including epidemiology, typical presentation, evaluation, and management, is followed by a discussion of the clinical and functional implications of the disorder in an emerging adult population. The authors conclude that CM-I is an important diagnostic consideration in the differential diagnosis of a young adult presenting with a chief complaint of chronic headache. It is vital for the college health practitioner to perform a detailed history on all such patients, placing special attention on factors that exacerbate their symptoms. The presence of worsening symptoms with cough or other forms of straining should prompt further investigation that includes neuroimaging of the brain and cervical spine.