This study examined how urban high-school students responded to increased academic expectations. The intervention included increased expectations for reading and writing, collaboration, and the completion of multi-day assignments. Twenty-four students (8 lower, 8 average, and 8 higher performers) from 4 classrooms were interviewed across a 9-week period to evaluate their reactions to the increased expectations. While students approached lessons with learning versus performance orientations, they were unsuccessful because they could not transfer classroom successes to their outside of school studying efforts. Their difficulties were related to a lack of strategies, a failure to manage distractions, or an inability to monitor studying behaviors. Discussion focuses on the difficulties among students based on performance levels and on the challenges of increasing academic expectations within a climate of high-stakes testing.