‘School connectedness’ is one of a number of terms used to describe a young person's relationship to school. With school being a compulsory feature of most young people's lives, the nature of this relationship can be highly influential in terms of the quality of their overall school experience. Young people experiencing low connectedness are more likely to withdraw from school and experience the parlous outcomes that often follow. This study used a mixed methods approach to explore the meanings of being connected with school, how this process is understood by students and staff, and how it is shaped by school and individual factors. The study was conducted at a secondary college in outer metropolitan Melbourne. Data collection involved a student questionnaire, student and staff focus groups, and student diaries. Findings indicate that that year level, cigarette use, and involvement in the choice of school were associated with significant differences in connectedness scores. Qualitative data revealed that students experience their connection to school through the relational, activity-based, and academic opportunities available to them in the school setting. It is argued that the findings from this study could be used to frame effective risk reduction or protection-enhancing interventions in schools.