An important goal of history education is to promote the student’s ability to perform historical perspective taking (HPT). HPT refers to the ability to understand how people in the past viewed their world at various times and in various places to explain why they did what they did. In this study, we assessed a sample of 15- and 16-year-old students (n = 143) to determine their ability to contextualize the actions of people in the past. Subsequently, we explored their reasoning (n = 36) to uncover their contextualization process. The results of this mixed methodology study indicate that most of the students in the sample performed well when engaging in HPT. Moreover, protocol analysis identiﬁed the different reasoning strategies that students employed to successfully perform HPT. The results of this study provide insight into history instruction regarding HPT and into strategies for designing valid and reliable HPT tasks.