In the aftermath of COVID-19, it is important to examine the different aspects of educational IT use in their respective contexts, including considerations to the potential well-being outcomes associable with IT use (e.g., technostress and related strains). In 26 semi-structured interviews with comprehensive school teachers, this study explores the challenges related to IT use in traditional (on-site) and online education. The results suggest that, although similar challenges can be identified in both settings (e.g., technical challenges and detrimental effects on teachers’ well-being), their prevalence and circumstances can vary. For example, while directing focus from IT use to schoolwork is viewed as a challenge for traditional education, reaching pupils and fostering interaction can become problematic for online education. However, the teachers have formed practices to address the challenges and can identify IT use-related opportunities for education as well. Future research should consider the multidimensionality of IT use that is present in different educational contexts