The extent to which students feel connected to their school is a powerful predictor of many health, social and academic outcomes. These outcomes are also influenced by other factors including characteristics of the school such as its size, policies and practices, but how do these characteristics modify the relationship between a student and his or her later school connectedness? This article draws on Western Australian data describing 5159 students from 39 schools who were tracked for the first two years of their secondary schooling. Controlling for interpersonal predictors of adolescent connectedness, the extent to which school characteristics, represented by school sector, modified later school connectedness was assessed using random intercept multi-level models. Significant interactions between school and individual student characteristics of interpersonal relationships as well as mental health were found for later school connectedness, suggesting the sector to which a school belongs influences a student's sense of connectedness to school. (Contains 5 figures and 2 tables.)