This study presents findings from an ethnographic content analysis of 15 chronological district-wide annual codes of student conduct from a large urban US school district. I frame policy creation and modification processes as reflections of societal shifts in perceptions of student behaviors. I looked to the policy documents to explore the possibility that school organizations have, over time, shifted toward school discipline frameworks that get students into deeper trouble today than in years past. The analysis yielded policy changes that, over time, make severe punishment increasingly likely. I refer to the change phenomena as "net-deepening" of school discipline. I address the pitfalls that net-deepening policy changes pose, with an emphasis on the potential for net-deepening to undermine the effectiveness of proactive and restorative forms of school discipline. The article offers to educators, policy-makers, and researchers conceptual and analytical considerations for developing proactive restorative discipline policies that meets the educational needs of all students.