Though researcher dilemmas are not new to the pages of Qualitative Inquiry, we argue that the current contemporary context has both altered and intensified issues associated with conducting qualitative research within sites most affected by more recent social, political, and economic shift. Navigating such sites as researchers poses new questions and new “speed bumps,” going well beyond those highlighted by Weis and Fine more than ten years ago. In this article, the authors revisit and extend the work by Weis and Fine using a set of informed reflections on engaging ethnographic research inside an iconic and beleaguered, large Northeastern, urban school district, a context that, we argue, establishes an increased range of new and largely unanticipated “speed bumps.”