This study is the first to estimate main, mediated, and moderated relationships between policy-assigned observations and various student discipline outcomes (SDOs). We also examined the relationships between SDOs and observations conducted. The data suggest that the percentage of students who receive at least one SDO decreases as policy assigns schools an additional 25 observations and that in-school suspension reductions drive this relationship. Improvements in teachers' classroom management skills mediate some SDO reductions. We found that several relationships substantively depend on the degree of prior-year SDOs and the average teacher's years of experience. While policy-assigned observations determined by teacher human capital measures may reduce SDOs, observations conducted for unobserved reasons may not.