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This case study presents our experiences, insights, and the pedagogical techniques used to guide undergraduate students toward discipline-specific thinking. It demonstrates the role of student-centered practices in moving students from what we categorize as novice to proficient, a common goal in rite-of-passage courses across the disciplines. Our study follows two semesters of students in undergraduate college-level Historiography and Historical Methods courses to identify common stumbling blocks encountered when learning contextualization (our discipline-specific thinking skill). We analyze students’ habits of mind, cognitive behaviors, and assumptions when learning to think differently. We present a qualitative portrait demonstrating the range of student cognitive behaviors as they attempt to move towards proficiency. As experts immersed in our fields of study and its practices, we can sometimes forget that what comes second-nature to us is far from natural to our students—regardless of their enthusiasm. We may overestimate the background knowledge that our students have, and underestimate the brain bandwidth required when trying—for the first time—to think differently.