In this article, we explore the roots of thoughtfully adaptive teaching in reflection. Drawing on the conceptual work of Dewey and Schon, we examine reflective practice in teaching as a tool for resistance against institutional pressures to standardize teaching practices. We describe 2 programs of research related to this topic. One program of research is focused on teacher adaptations to practice in the classroom. The second program of research is focused on coaching teachers to develop strategies for thoughtfully adaptive teaching. We draw on the work of Janks around deconstruction and reconstruction for critical teaching practices.