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A global pandemic is challenging our approach to schooling, yet accountability standards for teachers remain the same. Given this, it is important to understand how teachers in technology-rich schools make sense of accountability and their instructional effectiveness to meet the learning needs of underserved student populations. This multiple-case study analyzes teachers’ appraisal of their state mandated evaluation rubric and perceptions of their teaching effectiveness across three middle schools with 1:1 laptop initiatives. Our findings suggest that accountable leadership can mitigate potentially negative views of the evaluation tool and process. However, when the tool and school vision do not include explicit attention to culturally relevant and responsive pedagogy, student academic improvement can be viewed through an acultural lens.