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During the COVID-19 pandemic, more teachers than ever before turned to technology to engage students in learning. This study explores teachers’ (N=334) experiences with, and challenges faced, while teaching remotely with technology. The findings from the study indicate that the majority of participants used digital tools and apps that typically replicate traditional classroom practices and that many participants faced significant challenges when trying to teach remotely with technology. Given that technology has been hailed as an agent of change for teaching and learning, this paper considers why technology may not have lived up to its potential in a time of immense need.