OBJECTIVES: This study examined the relationship between self-reported empathy and breaking bad news (BBN) communication skills performance in a sample of undergraduate medical students (n = 100) in the clinical years of their program. METHODS: Correlational and regression analysis examined the relationship between Jefferson Scale of Physician Empathy (JSPE-S) and Empathy Quotient (EQ) scores, and communication skills performance based on students' application of the SPIKES protocol to a BBN scenario in a simulated encounter. RESULTS: Higher BBN communication skills performance was positively correlated with scores on the "Social Skills" EQ sub-scale (r (99) = 0.31, p = 0.002), which measures spontaneous and context-independent use of social skills. Multiple regression confirmed that "Social Skills" sub-scale variation predicted BBN score variation (B = 2.17, 95% CI = 0.65-3.69, p < 0.01). A weak positive association was also observed between BBN score and the "Standing in Patient's Shoes" JSPE sub-scale (r (99) = 0.22, p = 0.03). CONCLUSIONS: Findings suggest that specific aspects of dispositional empathy may moderate BBN communications skills competence in medical students. PRACTICE IMPLICATIONS: A better understanding of the moderating role of personality may lead to more tailored BBN communications skills training interventions and improved transfer of skills to workplace settings.