Background Persistent psychosocial stress is endemic in the modern workplace, including among midcareer high school (secondary comprehensive) teachers in England. Understanding contextual influences on teachers' self-management of stress along with their use of digital health technologies could provide important insights into creating more usable and accessible stress support interventions. Objective The aim of this study was to investigate the constraints on stress management and prevention among teachers in the school environment and how this shapes the use of digitally enabled stress management tools. Methods Semistructured interviews were conducted with 14 teachers from southern England. The interviews were analyzed using thematic analysis. Results Teachers were unanimous in their recognition of workplace stress, describing physical (such as isolation and scheduling) and cultural (such as stigma and individualism) aspects in the workplace context, which influence their ability to manage stress. A total of 12 participants engaged with technology to self-manage their physical or psychological well-being, with more than half of the participants using consumer wearables, but Web-based or smartphone apps were rarely accessed in school. However, digital well-being interventions recommended by school leaders could potentially be trusted and adopted. Conclusions The findings from this study bring together both the important cultural and physical contextual constraints on the ability of midcareer high school teachers to manage workplace stress. This study highlights correlates of stress and offers initial insight into how digital health interventions are currently being used to help with stress, both within and outside high schools. The findings add another step toward designing tailored digital stress support for teachers.