INTRODUCTION: Surgical residents often need to break bad news (BBN) to patients and family members. While communication skills are a core competency in residency training, these specific skills are rarely formally taught. We piloted a simulation training to teach pediatric surgical residents how to compassionately BBN of an unexpected, traumatic pediatric death to surviving family members. This training was unique in that it was influenced by family systems theory and was a collaborative effort between our institution’s surgery residency and medical family therapy (MedFT) programs. METHOD: This study provides outcomes of surgery residents’ communication skills, attitudes, and self-perceptions after a BBN simulation activity with standardized family members at a major academic teaching hospital. Each resident participated in two 30-min simulations and received feedback from observers. Outcome data were collected through self-assessments completed before, immediately after, and 6 months after the simulation. Participants were 15 surgery residents, and MedFT students served as simulated family members and trainers. RESULTS: A statistically significant change with medium to large effect sizes in participant self-reported perceptions of skill and confidence were documented and maintained over 6 months. Responses to open-ended questions supported practice changes in response to the training. DISCUSSION: This collaborative training promoted significant improvement in resident compassionate communication skills. The curriculum was highly valued by the learners and resulted in sustained application of learned skills with patients and families. Our novel approach was feasible with promising results that warrant further investigation and could be reproduced in other institutions with similar programs. (PsycINFO Database Record (c) 2018 APA, all rights reserved).