The impossibility of knowing in advance what might be ethically contentious in ethnographic research is exemplified by the dilemmas faced by having a multitude of inside and outside positionalities that are often fluid and evolve throughout a study. Based on active interviews and fieldwork in two studies of police and bylaw officers and municipal officials, this article reflects on unanticipated ethical challenges arising throughout the research process, from the recruitment of participants to obtaining informed consent to trying to “fit in” as both insider and outsider. The resulting tension is unavoidable, inevitable, and generates new insights based on actual experiences that are often unforeseeable. Ethnographers accordingly rely on their own instincts when deciding what is ethical rather than fixed protocols prescribed by Research Ethics Boards. To complicate things further, note the authors, such dilemmas are a manifestation of evolving power relations between researchers and informants and institutional gatekeepers needed to gain access, but with differing priorities than those imposed by REB regimes.