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In intensive care settings, suboptimal communication can erode family trust and fuel so-called “futility” disputes. Presenting a teaching case used by >225 hospitals participating in the Decisions Near the End-of-Life program, we identify critical communication challenges and opportunities. We emphasize that good communication requires not only clear and sensitive language but also clinician self-awareness, psychological insight, and an institutional culture that promotes good communication with families. The article concludes with two examples of steps institutions can take to foster good communication between families and healthcare professionals.