Abstract Lewis Carroll’s Alice’s Adventures in Wonderland ( 1865 ) and Through the Looking-Glass ( 1871 ), two linguistic treatises in disguise, create ingenious fantasy worlds where the rules of language and the conventions of communication are turned upside down. What is (semantically) illogical or (pragmatically) inappropriate confounds Alice, who struggles to make sense of nonsense and to keep the order of a polite, rational world in place. In her dialogues with anthropomorphic animals and objects, ambiguity and fallacy coexist with interactive manipulation, while her communicative expectations crumble and comic misunderstandings arise. This article looks into the construction of linguistic and pragmatic transgressions in Carroll’s acclaimed books with a view to unveiling their contribution to impoliteness. On the one hand, the paper analyses the structural mechanisms of wordplay vis-à-vis phonetic, morpho-syntactic and lexical ambiguity. On the other, it examines the pragmatic strategies whereby speech-act infelicities, conversational maxim violations, and bald-on-record clashes contribute to reversing the established conventions of (polite) social interaction. The premise guiding the analysis is that the pervasive existence of double meaning and incongruity in the Alice books underlies not only linguistic phenomena such as punning, neologism, and relexicalisation, but also interactive patterns, in which the expected norms of courteous conduct in social exchanges do not obtain. The antithetical and script-oppositional (hence, humorous) nature of this process defrauds outsider Alice – the victim, but at times the happy recipient, of the uncooperative challenges of this inverted, refracted, teasingly nonsensical world.