We employed qualitative research methods to examine student learning in context during a teacher's unit on 1920s-Great Depression in an 11th grade United States & Virginia History class in a standards-based setting with a high-stakes end-of-course test. We focused on four focal students (all of whom were classified as English learners at some point during their education) and collected extensive data to investigate whether these students learned and how they experienced and described their learning from regular classroom instruction. Despite receiving the same instruction, student learning, as measured by the summative assessment, differed greatly, and it was unclear if students learned the historical content. Teaching to the test (e.g., lecture-focused, didactic, narrow fact-focused instruction) did not yield improved results on the multiple-choice test. These findings problematize the use of multiple-choice testing, emphasize the need for explicit academic vocabulary scaffolds for multilingual learners, and highlight the importance of formative assessment. We argue that the conception of teacher as curricular-instructional gate-keeper needs to be expanded to curricular-instructional-assessment gate-keeper.