Emergency department visits for a headache are relatively common, and in most cases, the etiologies of the headache are typically benign. We present a case of a patient who presented to the emergency room for new onset of unremitting unilateral headache. She subsequently had two hospital visits and three separate imaging modalities to identify vein of Labbe thrombosis. The vein of Labbe is a relatively smaller vein which runs superficially and laterally. In our patient, a cerebral venous thrombosis (CTV) was unable to identify vein of Labbe thrombosis, requiring eventually a magnetic resonance imaging (MRI) with and without contrast to identify the culprit etiology. CTV is frequently used in the acute setting due to its speed of acquisition and shorter wait times in the hospital. For patients that fit criteria for venous sinus thrombosis, we caution the use of CTV in identifying the causative etiology, and would consider the MRI as a better imaging modality for these patients.