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This chapter acknowledges that many students are falling through the gaps of Ontario’s current education system. Rigelhof seeks to understand the consequences of labeling students as ‘at-risk,’ and will critically engage with the stereotypes surrounding urban schools. This chapter focuses on the 34 schools that are a part of the Ontario Ministry of Education’s initiative: Urban and Priority High Schools. By critiquing deficit thinking and stereotype threat theory as conceptual frameworks, through the theoretical frameworks of critical anti-racism theory and anti-colonial theory, this work aims to deconstruct these ideals and determine ways in which educators can move away from such thinking into more inclusive practices. Rigelhof posits that this will result in greater student success for those who are labeled ‘at-risk.’ The current literature surrounding deficit thinking and urban schools is lacking in the sense that there has not been critical and in-depth focus and analyses of the Urban and Priority High School initiative. Rigelhof acknowledges that this research may change over time; however, deconstructing the stereotypes applied to ‘at-risk’ students is a necessary endeavour in gaining greater student achievement.