In the paradigmatic shift to online teaching during the pandemic, school teachers were forced to take the lead and responsibility of making the online transition happen. In this study, we seek to understand how teachers experienced the digital transition. Specifically, we examine how technology mediated work practices and its implications for employee well-being. The study adopts sensemaking as a theoretical lens since it allows us to examine, and rationalize actions taken in uncertain times. The findings highlight that while technology played an important role in the digital transformation in schools, the impact of its intertwining with work practices on well-being of teachers was mixed. On one hand it enabled continuity of business, but on the other it led to blurring of work-life boundaries as teachers had to invest time and effort to change teaching pedagogy, develop their technical skills and competencies, and manage conflicting expectations and demands at home. Further, technology affordances enabled thru online teaching increased precariousness of work.