The objective of the present investigation was to clarify the role that anxiety sensitivity (AS) and other related constructs play in headache medication use in patients with recurring headaches. A total of 108 patients (88% female) with chronic recurring headaches (mean duration = 205.6 months) provided complete responses to a self-report inventory administered during a treatment visit to an outpatient neurology clinic. The inventory included measures of depression, trait anger, trait anxiety, fear of pain, AS, and the impact of headache on daily living. AS and fear of pain were used in accordance with their multidimensional conceptualizations. Hierarchical multiple regression analyses were conducted to determine the variables that contributed significantly to the prediction of current over-the-counter analgesic and prescription medication use. After controlling for pain severity, the cognitive anxiety dimension of fear of pain was the only significant predictor of over-the-counter analgesic use. For prescription medication use, the fear of physical catastrophe dimension of AS and the physiological anxiety dimension of fear of pain were significant predictors, although the predictive direction of the former was opposite to that found in prior studies. The models, while significant, accounted for relatively small amounts of variance. Implications of these results and issues of medication abuse and dependency are discussed.