Educator well-being is of immense importance to student success, yet rising instances of educator stress, burnout, and attrition can lead to lowered levels of well-being. While educators' experiences with stress, burnout, and attrition can involve multiple factors, researchers have noted the convergence of mindful attention awareness and educator well- being as an instrumental influence in educators' capacity to remain in the profession. This mixed methods portraiture-inspired study explored the convergence of mindfulness and well-being of educators employed by a school district that recently started a mindfulness initiative to support educator well-being. The study took place over the course of 18 weeks, with data derived from (a) the Scales of Psychological Well-Being (Ryff, 1989); (b) Mindful Attention Awareness Scale (Brown & Ryan, 2003); (c) interviews; (d) classroom observations; (e) exit tickets; (f) researcher participation in the district's mindfulness initiative offerings; and (g) visits to the schools and surrounding neighborhoods. Results from the quantitative data revealed that mindful attention awareness predicts psychological well-being. Results from the qualitative data provided further insight into educators' experiences with mindfulness, well-being, and the educational system factors that impact educator stress. Themes included the cultivation of meaningful growth opportunities; the importance of fostering positive relations with others; and the impact of top-down leadership on environmental mastery. The findings from this research highlight a need for educational organizations to utilize organizational-wide, mindfulness-based, professional development opportunities to more effectively support educator well-being. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]