The use of educational technology as society emerges from COVID-19 continues to pose a challenge for educators. There is a lack of evidence on how digital technology can positively impact teacher wellbeing when effectively managed by school leaders and teachers. This research sought to explore and develop the connection between educational technology and teacher wellbeing, using Passey's (2021) framework and proposition that specific digital technology adoption in schools can benefit teacher well-being in various educational contexts. Six schools, three primary and three secondary, in Northern Ireland and the Republic of Ireland, were studied through in-depth case studies focusing on teacher wellbeing and technology adoption. Interviews were conducted with school principals, leaders, and teachers. The results of the study include that while teachers readily discuss the impact of technology on their work, they are less likely to reflect on its impact on their physical, social, and emotional wellbeing.