In his seminal volume From anxiety to method in the behavioral sciences, George Devereux suggests that any therapeutic or scientific engagement with another human being inevitably will be shaped by one's own expectations, assumptions, and reactions. If left unacknowledged, such unspoken and unconscious influences have the capacity to torpedo the interaction; if subjected to critical reflection, however, they can yield insights of great interpretive value and practical significance. Taking these reflections on counter-transference as point of departure, this article explores how a range of unacknowledged assumptions can torpedo good faith efforts to engender "cultural sensitivity" in a required course for American psychiatry residents. The course examined in this paper has been taught for seven successive years by a pair of attending psychiatrists at a longstanding New England residency training program. Despite the instructors' good intentions and ongoing experimentation with content and format, the course has failed repeatedly to meet either residents' expectations or, as the instructors bravely acknowledged, their own. The paper draws upon a year-long ethnographic study, conducted in the late 2000s during the most recent iteration of the course, which involved observation of course sessions, a series of interviews with course instructors, and pre- and post-course interviews with the majority of participating residents. By examining the dynamics of the course from the perspectives of both clinician-instructors and resident-students, the paper illuminates how classroom-based engagement with the clinical implications of culture and difference can run awry when the emotional potency of these issues is not adequately taken into account.