Typically, political consumerism is portrayed in straightforward, unproblematic ways. This chapter discusses how and why political consumerism—and particularly boycotts—can be confusing and problematic. Theoretically it focuses on moral dilemmas within political consumerism and the key role of overriding moral claims in the motivations for and actions of political consumer causes. An ideal type model, constructed for analyzing unproblematic and problematic political consumerism, is applied to cases of more unproblematic political consumerism (e.g., the Nestlé, Nike, and South African boycotts) and more problematic political consumerism (e.g., the Disney boycott and the movement against Israeli settlements in the occupied Palestine territories). The chapter also addresses why other forms of political consumerism (buycotts and discursive actions) seem less vulnerable to moral dilemmas as well as the research challenges in studying more problematic cases of political consumerism.