Some women in a high-risk pregnancy go against medical advice and choose to birth at home with a “holistic” midwife. In this exploratory multiple case study, grounded theory and triangulation were employed to examine 10 cases. The women, their partners, and (regular and holistic) health care professionals were interviewed in an attempt to determine whether there was a pattern to their experiences. Two propositions emerged. The dominant one was a trajectory of trauma, self-education, concern about paternalism, and conflict leading to a negative choice for holistic care. The rival proposition was a path of trust and positive choice for holistic care without conflict. We discuss these two propositions and make suggestions for professionals for building a trusting relationship using continuity of care, true shared decision making, and an alternative risk discourse to achieve the goal of making women perceive the hospital as safe again.