Instructional consultations are often challenging, but some are frustrating for reasons that are unrelated to teaching per se. There is a prolific literature on consultations, but most of it assumes that the instructor is ready, willing, and able to take suggestions. In the authors’ experience, this is not always the case, and consultations can become “entangled” in a web of interacting, compounding factors exogenous to teaching. They analyze entangled consultations to identify common themes and strategies for responding appropriately. The compounding factors that the authors consider include defensiveness, personal problems, cultural reasons, or departmental politics. The authors also present four case studies condensed from their own experiences in entangled consultations and offer suggestions for using them to build the scholarship of educational development.