Through exploration of Black Caribbean youths' feelings of unbelonging and exclusion in Ontario schools, this paper argues that how Whiteness is systemically engrained in the education system negatively affects the learning experiences of Black youth due to predetermined measures of belonging. The present article draws on data from 32 qualitative interviews and four focus groups with 23 Black Caribbean youth. Findings reveal challenges youth commonly face when navigating relationships with peers and educators that hinder their academic success. These challenges are exacerbated for youth who are also involved in the state's child protection system. Participants described feeling disadvantaged in the education system due to perceptions that they are academically unprepared and thus unable to excel. Through a Critical Race Theory and Anti-Black Racism analytical framework, the findings illustrate how systemic barriers coupled with the normalization of low expectations impact the educational success and opportunities of Black Caribbean youth in Ontario schools.