This article explores the reasoning employed by high school students to answer a set of multiple-choice history questions. The questions come from New York State's Global History and Geography Regents exam. The Regents exams, together with a particularly well-regarded and ambitious set of content standards, are the cornerstone of the state's standards-based accountability system. Using "think-aloud" and interviews with a small sample (n=13) of urban 10th graders, the knowledge and skills elicited by a small sample of items are explored. This article begins with a discussion of the state standards and the discipline-based knowledge and skills that they describe. It continues with a report on the extent to which the student-participants were exposed to the material included in the administered items by a teacher whose pedagogy was commensurate with state standards. The bulk of the paper focuses on two test items that were particularly effective at discriminating between high and low performers. The reasoning and knowledge employed by participants when answering these questions are explored. The findings support previous research indicating that the assumptions made by adults about what items measure are often only partially correct. In the case of the items included in this study, they appeared to evoke knowledge and skills in three domains - history content, literacy, and test-wiseness - but not the discipline-based thinking so highly prized by the standards.