"Contextualization", the act of placing events in a proper context, allows teachers to weave a rich, dynamic portrait of a historical period for their students. As teachers strive to identify enduring themes and patterns, they must teach students to appreciate the particular policies, institutions, worldviews, and circumstances that shape a given moment in time. However, contextualized historical thinking runs counter to the narratives and frameworks that many students bring to class. Not only have many young people internalized timeless, psychologized notions of why people behaved as they did in the past, but they have also absorbed powerful stories through popular culture. Challenging long-standing historical frameworks takes time, and educators must give students multiple opportunities to practice and apply their new knowledge and skills. In this article, the authors describe three activities that help students think contextually as they read historical documents: (1) providing background knowledge, (2) asking guiding questions, and (3) explicitly modeling contextualized thinking. (Contains 1 figure.)