This chapter distinguishes different manners through which individuals and collective entities engage in reprehensible behavior and, on that basis, identifies two general contexts of wrongdoing: (1) a one-on-one context involving tortious situations where one individual directs her conduct toward another specific individual and (2) a collective context, which refers to tortious situations arising from impersonal market transactions between consumers and corporations. Each context of wrongdoing provides a framework from which distinctive understandings of punitive damages can be explored, one where the retributive reaction seeks to address invasions of dignitary interests and another for cases in which the retributive reaction responds to violations of societal trust. Ultimately, the chapter argues that any informed conversation on the place of retribution in the mass-market context requires improved understandings of the relevant markers for reprehensible behavior in that context (particularly the problem of asymmetry of information between manufacturers and consumers) and the correlative retributive motivations of consumers elicited in those wrongful situations.