The U.S. education system finds itself at a moment in history when district leaders are expected to address questions of student and educator well-being as they never have before, weighing decisions related to how to provide in-person instruction safely, how to support students’ and educators’ social and emotional well-being in the context of stress and adversity experienced outside of school, and how to keep students psychologically and emotionally safe from bias and discrimination at school. A previous brief summarized the experiences and recommendations of a practitioner and several district leaders who are working to reexamine their districts’ systems, structures, and policies to ensure they support the well-being and learning of all students. This accompanying brief provides those leaders’ thoughts in their own words.