Calcific tendinitis of the longus colli can present acutely with headache, neck pain, and dysphagia, as was the case here. The bedside clinicians favored a musculoskeletal etiology but pain persisted despite muscle relaxers and acetaminophen. Although the imaging was obtained to evaluate for arterial dissection, the findings of prevertebral edema and tendon calcification were helpful in confirming the musculoskeletal etiology and additionally prompted anti-inflammatory therapy. Prednisone was prescribed (as opposed to the more typical non-steroidal anti-inflammatory drug due to also taking oral anticoagulation, which increases bleeding risk) and symptoms improved.