In Ancient times and in the contemporary moment, kairos has operated as a keyword for theorizing rhetoric and its potential. Aligning ourselves with these endeavors we take stock of varying iterations of the kairotic not to artificially force a singular conception of the term, but to hold such resolutions at bay. We assess efforts to realign kairos with challenges to the ontological priority of rhetorical actors and trace recent theoretical articulations that further decenter human agency by relocating the kairotic in ecological/contextual forces. We assert the need to maintain invention and eventfulness as crucial elements of the kairotic so as to insist that rhetoric be understood as a practice that exceeds socio-anthropological “adaptation” to those conditions. Through a series of propositions we hold hope for an inventive and evental kairotic stance that likewise avoids naïve conceptions of sovereign subjectivity.