The current study examined whether students’ perceptions of school disorder influenced their psychosocial outcomes directly and indirectly via connectedness to school. The current study also explored moderation by the presence of a supportive figure in the school and investigated gender differences. Participants were 28,104 high school students. Results indicated that students’ perceptions of school disorder predicted more externalizing behaviors and internalizing symptoms directly and indirectly via reduced connectedness to school. Perceived school disorder also indirectly predicted lower academic grades. The presence of a supportive figure in the school lessened the detrimental influence of school disorder on student outcomes. Results also indicated that male students may stand to benefit more from the protective influence of a supportive figure in the school.