Chronic pain is often an ongoing challenge for patients to track and collect data. Pain-O-Vision is a smartwatch enabled pain management system that uses computer vision to capture the details of painful events from the user. A natural reaction to pain is to clench ones fist. The embedded camera is used to capture different types of fist clenching, to represent different levels of pain. An initial prototype was built on an Android smartwatch that uses a cloud-based classification service to detect the fist clench gestures. Our results show that it is possible to map a fist clench to different levels of pain which allows the patient to record the intensity of a painful event without carrying a specialized pain management device.