Physicians who treat injured workers with painful conditions face complex challenges that require skills beyond those of a clinician. To address these challenges effectively, physicians need to understand the logic of workers’ compensation systems and the interests of the various participants in the systems. They must be prepared to interface constructively between their patients and the workers’ compensation carrier and attend to a multitude of administrative issues. In the present article, the authors provide an extended case history with commentary to illustrate the challenges that physicians face and the ways they can respond to these challenges.