Although teacher education for U.S. K-12 urban contexts continues to encourage preservice teachers to develop cross-cultural and historical understandings of students, relatively little scholarship has explored how teachers construct and operationalize culturally-proactive pedagogies in ethnic studies coursework. In this article, we narrate the experience of Paul Roberts, a White, male teacher, as he endeavored to enact a culturally-proactive pedagogy when working with a diverse group of students in a newly created Latinx American Studies class. Specifically, we draw on literature about wobble, Whiteness and culturally-proactive pedagogy to frame our analysis of Roberts’ s narrative. We organize our representation around three tensions—1) determining authenticity, (2) cultivating dialogue and (3) navigating expectations—that Roberts experienced as he wobbled within his teaching. Drawing from our findings, we suggest a (re)framing of failure and positionality in a way that celebrates uncertainties. Teachers, particularly White teachers, tasked with such nuanced work need ongoing support and opportunities to reflect as they navigate the wobble inherent in developing a culturally-proactive pedagogy—even more for a course that highlights the histories of a group with which they do not identify.