Teaching graduate family nursing students the important and delicate practice of entering into and mitigating families' illness suffering signifies an educational practice that is rigorous, intense, and contextual, yet not articulated as expounded knowledge. This study examined the pedagogical practices of the advanced practice of Family Systems Nursing (FSN) as taught to master's and doctoral nursing students at the Family Nursing Unit, University of Calgary, using observation of expert and novice clinical practice, live supervision, videotape review, presession hypothesizing, clinical documentation, and the writing of therapeutic letters to families. A triangulation of research methods and data collection strategies, interpretive ethnography, autoethnography, and hermeneutics, were used. Students reported an intensity of learning that had both useful and limiting consequences as they developed skills in therapeutic conversations with families experiencing illness. Faculty used an intentional pedagogical process to encourage growth in perceptual, conceptual, and executive knowledge and skills of working with families.