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Using data collected from a year-long ethnography of four fourth-grade classrooms in two public elementary schools that that serve low-income communities, this paper examines the compounding constraints teachers face when trying to effectively teach their students. More specifically, I analyze both top-down district- and school-level pressures; alongside bottom-up individual-level constraints that arise from teaching poverty-stricken students, to better understand how these multi-level mechanisms operate through day-to-day classroom interactions and experiences. In-depth Interviews conducted with all four teachers at the beginning and the end of the 2023-2024 academic school year, combined with weekly classroom observations and casual conversations during the year provide key insight into poverty as a key influence over classroom experiences, in ways that often stall or reverse the impact of what might otherwise be successful academic remediation strategies. I find that District-level policies place tremendous pressure on schools to raise student performance, leading to school-level administrators pursuing ways to provide evidence that they are working on these goals, sometimes at the expense of time spent working on the goals themselves. For example, insisting teachers conduct reading-fluency assessments for every student weekly, forcing teachers to devote several hours a week assessing reading skills, instead of spending that time helping students develop strategies to improve those reading skills. A better understanding of how these compounding top-down and bottom-up constraints shape classroom interactions and experiences will help ensure that future education interventions are suited to meet the specific needs of each classroom rather than a one size fits all approach.