Historical empathy scholarship has evolved to the point where further progress necessitates empirical examinations from a variety of perspectives. Prior studies on historical empathy have largely focused on teachers' pedagogical approach and student outcomes. This qualitative study focuses on students as they engage in the process of historical empathy to deepen our understanding of how they reach desired curricular and dispositional outcomes. Using an updated theoretical and instructional model for historical empathy as a cognitive-affective construct, a group of high school students engaged in historical empathy to better understand Harry Truman's decision to deploy the atomic bombs at the end of World War II. Results suggest that students are greatly influenced by identification, modern perspectives, shared human experience, and affective connections when engaging in historical empathy. The findings hold implications for developing historical understanding and dispositional appreciation for the past.