The COVID-19 pandemic created substantive stress and uncertainty for secondary educators, including responding to the shifts in delivering education from the traditional to the online classroom and back to the classroom. Improper training, increased work demands, increased responsibilities, and decreased autonomy took a toll on teachers' work and home life. To better understand how teachers deal with transitions in online, hybrid, and in-person education, this study explored secondary educators' experiences of psychological well-being during the transitions from in-person to online teaching. An interpretative phenomenological approach guided the research design. Lazarus and Folkman's transactional theory of stress and coping was used as the framework for exploring coping with stress during transitions. Demerouti et al.'s job demands-resources theory was used to explore the role of social support in responding to job demands. Semi-structured interviews were conducted with seven educators to explore the experience of well-being and social support during their transitions. The results revealed positive and negative thematic dimensions for well-being and social support. Future studies could explore administrators' perspectives and consider what interventions for well-being would contribute to reducing stress. The results may contribute to positive social change by emphasizing the consequences of such transitions and encouraging school administration to build opportunities for resources and social support that can facilitate well-being at work. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]