1:1 laptop schools have increased over the past decade, yet minimal research exists that focuses on classroom observational practices within such schools. This study examines how teachers and school administrators from three 1:1 laptop Title 1 schools perceived standardized teacher evaluation systems and classroom observation practices. Findings revealed misaligned instructional expectations and the need to reconceptualize classroom observation supervision and evaluation tools for 1:1 laptop classrooms. Participants of this study agreed that teacher evaluation rubrics did not help identify effective instruction with technology. School administrators and policymakers must reconsider the standards and tools used to evaluate 1:1 laptop instruction.