This case study follows an early-career teacher from an undergraduate educator preparation program into her first teaching position in an urban high-stakes charter school organization. At the beginning, the cognitive dissonance between her emergent educational philosophy and the extreme features of the charter school environment, such as the scripted curriculum and zero-tolerance management system, destabilize the young educator. Empathy for her students resets understandings of allegiance, agency, community, and learning. Framed by literature on adaptive expertise, this study raises questions for teacher educators about adaptive praxis in challenging teaching environments. Promoting resilience over resistance may encourage more nuanced and opportune professional dispositions in early-career contexts.