From stigmatizing publicity to coerced gestures of public contrition to ritualized debasement ceremonies, shaming penalties are on the rise in American law. This paper considers the feasibility and value of such penalties for federal white-collar offenders. It develops a theoretical model that connects the deterrent efficacy of such penalties to their power to signal the undesirable propensities of wrongdoers and the desirable propensities of citizens who shun wrongdoers. It also considers how the efficiency of such penalties is affected by their power to express publicly valued social meanings. Finally, it examines practical issues relating to the incorporation of shaming penalties into the Federal Sentencing Guidelines.