This chapter addresses the notion of historical empathy in students and its development through an active process, which is embedded in a historical method. The authors discuss four main phases: a historical event that requires the analysis of human action, understanding historical context and chronology, analysis of historical evidence, and interpretations and construction of a narrative framework. The authors focus on subject matter from WWII and discuss two different instances of historical empathy with their students. They based their research questions on the 1987 work of author C. Portal. The first exercise was based on President Truman’s decision to use atomic weapons during WWII. The authors created a preliminary study and used a writing exercise to help determine students’ use of historical empathy and how the use of different sources affected their responses to the questions. The second exercise described by the authors was a teacher-directed classroom exercise concerning President Truman’s decision to drop the atomic bomb. They used a pretest with four questions and then focused on eighteen documents on President Truman’s decision, to which they had to answer eleven questions. The authors conclude with four main findings from the two different exercises. The teaching of historical empathy, as discussed by the authors, is a challenging feat and can be time consuming. Students learned better when the teacher acted as a facilitator and not as a deliverer of knowledge.