This study is an exploration of how U.S. middle school students interacted with different topics in world history, and how their specific understandings of topics were connected to both sociocultural and instructional contexts. I observed two world history classrooms in a Midwestern Catholic school for 10 months and conducted task-based group interviews on 6 topics with 66 students. Findings indicate that students interacted differently with different topics, and their understandings of the given topics aligned with prior conceptions, situated in their sociocultural contexts, and teacher instruction in a complicated process. At times, the teachers' instruction accommodated students' prior conceptions, strengthening their misunderstandings. Certain instructional strategies also evoked students' awareness of their current contextual values, such as democracy, human rights, and nonviolence, hindering them from rationally understanding different contexts in history. There were times, however, when the teachers' intentional instruction overshadowed prevailing discourses, allowing students to successfully construct new understandings. From these findings, I argue that to be prepared for the world of their future, U.S. students need to go beyond the parameters of their sociocultural contexts and develop a comprehensive understanding, both nationally and globally, of the world.