Chapter 6 returns to thematic historical controversies about advertising, to examine boundary work on the lines between advertising and so-called moral questions in the debates about gambling and indecency. These were the two areas in which uses of law came closest to conceptualizing enchantment. The theory of gambling in legislation and case law highlighted gamblers’ quasi-mystical views and ecstatic behaviours. The theory of indecency placed primacy on concepts of influence of the print object, which could draw affective responses beyond reason’s control, famously articulated in the 1868 case of R. v Hicklin. In both cases, the unstable boundary between popular culture and enchantment was crossed. They provided conceptual languages that could open up a broader debate about enchanting appeals. However, this conceptual possibility was curbed as the legal logic and practice applied to advertising shielded it from a developed discussion of the role of enchantment. To show this process, Chapter 6 explores select contexts: prize competition adverts, poster censorship, and the medico-legal campaign against adverts for abortion medicines. From differing directions and with no unified perspective, these all demonstrate how even with theories of enchantment at hand, and legal operations intended to apply them, the role of enchantment in advertising remained only minimally acknowledged, while advertising was once again theorized as an inferior part of a disenchanted culture—at that culture’s margins yet within its bounds.