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This paper offers an analysis of a robustly attested semantic change in which progressive markers “spontaneously” emerge in languages, become entrenched in the grammatical system, and diachronically generalize by turning into imperfective markers. The pattern is cyclic in that the generalization is often followed by a re-emergence of new progressive markers. The analysis has a semantic component that characterizes the relation between the progressive and imperfective operators as a privative semantic contrast. Its dynamic component rests on the proposal that imperfective and progressive sentences crucially distinguish between two kinds of inquiries: phenomenal and structural inquiries (Goldsmith & Woisetschlaeger 1982). The trajectory — consisting of the recruitment of a progressive form, its categorical use in phenomenal inquiries, and its generalization to imperfective meaning — is modeled within the framework of Evolutionary Game Theory. The diachronic path is reconstructed as a cyclic pattern in which alternative communication strategies rise and fall in dominance over time due to the differences in communicative success and learnability associated with them.