The differential diagnosis of headaches is very diverse, and they can represent the symptoms of life-threatening conditions that need to be addressed promptly. Vertebral artery dissection (VAD) can be manifested with isolated headaches, and it can be easily overlooked. It usually presents in younger patients along with some focal neurological symptoms. It is diagnosed with multiple imaging modalities. We present a case of a 38-year-old woman without evident risk factors and an isolated headache who was only diagnosed with a spontaneous VAD after multiple primary care office visits and even an urgent care facility before presenting to the Emergency Room. We will review the characteristics of the pain related to VAD to improve its identification in the outpatient setting. This is a potential area of research and quality improvement to diagnose and treat this condition promptly.