The Korean connective -mye exhibits an intriguing pattern in its grammaticalization into sentence-final particles. From the paradigmatic viewpoint, the form extends its membership from the paradigm of connectives to that of the sentence-final particles. From the semantic-functional viewpoint, the developmental path of -mye and its related forms proceeds from the concomitance, to diverse grammatical notions of conditionality, simultaneity, background, commensurability, adversativity, contrast, permissive modality, among others. Various syntagmatic operations bring forth -myense through formal reinforcement and further -tamyense (and those sharing the paradigmatic affinity) through fusional processes. Crucially involved in this development is the main-clause ellipsis, in which the addressee is compelled to reconstruct the elided main clause, a process where context-induced reinterpretations, or invited inferences, actively take place. Such reinterpreted meanings are actively being conventionalized to become a part of the semantics of the newly created sentence-final particle. A quantitative analysis reveals that the grammatical forms follow the path of the most frequently-used form that spearheads the change. Such changes are enabled purely by their semantic and morphosyntactic similarities, i.e. their paradigm membership, despite their extremely low token frequencies. This is contra two important hypotheses: that analogy is not a decisive mechanism of grammaticalization and that the high frequency is as essential as a prerequisite to set a condition for grammaticalization.