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As schools transitioned from the face-to-face classrooms to the remote environment due to the COVID-19 epidemic, the challenges of educational technology unveiled. Teachers are grappling with the “new normal” and on-going uncertainty. UNESCO (2020) noted that many teachers are dealing with the stress of delivering quality learning with tools for which they have received little training or support. This study examined the experiences of K-12 teachers to capture the level of classroom technology usage, teacher expertise, and preparedness for the transition to remote learning spaces. The findings indicate that despite access to technology, about 52% of teachers felt unprepared for the transition to remote education, and only about two-thirds of students participated or completed assignments during the 2020 school shut-down.