This chapter investigates the development of pragmatic markers and critique the argument that they develop gradually by means of the grammaticalization of lexical items (e.g., Traugott 1995). Specifically, it argues that what has been said to be gradual is necessarily a case of (potentially a series of) abrupt change(s). This idea is not unlike the Traugott and Trousdale (2010) discussion of micro–changes and Brinton and Traugott’s (2005:150) “tiny local steps between A and B that the arrow ‘>’ encompasses". The view here is a generative perspective on language change, adopting and adapting Roberts and Roussou’s (2003) generative approach to grammaticalization and Kroch’s (1994) discussion of morphosyntactic change. Arguments for abrupt change are drawn from an examination of the trajectories of change of epistemic parentheticals. In conceptualizing the development of pragmatic markers from a generative perspective, the chapter outlines a schematic of grammatical change for these systems that involves upward reanalysis similar to Roberts and Roussou (2003). The chapter concludes by pointing out that different theoretical perspectives on changes to pragmatic markers tend to dance around similar conclusions, and in many ways differences in vocabulary obscure similar understandings of how language changes.