According to the World Health Organization (WHO), schools have a unique opportunity to play a pivotal role in addressing mental health needs in their communities (Sawyer et al., 2021). The purpose of this phenomenological study was to examine the impact that the utilization of a system approach has on the success and sustainability of teacher well-being initiatives. The stressors teachers experience, which has been compounded by the pandemic, have induced trauma and stress, impacting their mental health and well-being, ultimately leading to burnout, decreased job satisfaction, attrition, and lower performance. Reinforcing the need for organizations to develop and utilize a systems approach to provide teachers with the layers of support needed to sustain and enhance teacher well-being (Greig et al., 2021). The study of this phenomena included the use of a pre-screening survey to solicit central office leaders in a three county range in Western Pennsylvania who had experience supporting teacher wellness initiatives. Respondents that selected at least ten of the 30 indicators were invited to participate. The researcher conducted semi-structured interviews with six of the respondents. Four dominant themes and five subthemes emerged as findings in the study: the need for wellness programming, prioritizing wellness, resourcing programs, the informal use of systems approach supported through the following subthemes: strategic partnerships and collaboration, teacher engagement, involvement, communication, and culture. The researcher discovered that the screening tool used was itself a finding and had potential additional wellness measuring benefits that need to be explored in future research. The study presented evidence that leaders can support teacher wellness utilizing a systems approach. [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.]