In this case narrative, senior superintendents reckon with the challenges of implementing a revised strategic policy for student discipline in an intensified work environment. Challenges include: (a) providing professional learning to familiarize leaders and educators with regulatory requirements; (b) a problematic trend of school and district leaders avoiding long-term suspensions; (c) the disproportionate number of minoritized students who are suspended/expelled; and (d) securing the resources needed to realize the punitive and preventative elements of the strategy. The case description is followed by three exercises--case framing, reflective practice, and action plan--that instructors can use in graduate-level courses and professional development workshops.