Workplace law activists and reformers find it increasingly more difficult to obtain redress for violation of workers’ rights. Some of them are calling for stricter enforcement and tougher penalties to bring employers into compliance. However, after seven and half months of participant observation at the Labor Directorate and the labor courts of Chile, institutions that use punishment as their main tools of enforcement, I am skeptical about the likelihood of success of mere punishment for effective workplace law enforcement and compliance. I am skeptical even though Chile is a country recognized as the Latin American “jaguar” for its successful economy and high respect for the rule of law. I observed that in Chile punishment bred a culture of resistance against workplace law enforcement. Some powerful employers mobilized courts and other government players against the labor inspectorate, the agency in charge of administratively enforcing all laws regarding the workplace, rendering the institution moot. My findings provide further evidence for New Governance, responsive regulation and traditional “Latin” inspection strategies being advocated by some law and policy scholars in the United States and beyond. While most of these scholars do not discard the importance of punishment, they call for more participatory and cooperative regulatory and enforcement processes, the use of persuasive rather than just punitive enforcement orientations, and conciliatory and remedial strategies by the enforcers to obtain better compliance results. In this manner, the Chilean case supports continued experimentation with non-punitive enforcement tools not just in Chile but also in the United States and beyond.