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This paper examines the relationships between classroom conditions (class size, composition, and pedagogical delivery mode) and teachers’ ability to engage in successful anti-racist teaching. This mixed-methods study draws on a survey and interview data from teachers in eight secondary schools in Toronto, Canada. Early data analyses offer three important findings: larger classes hamper successful anti-racist teacher practice; teachers are less effective in supporting and connecting with racialized students when teaching online; and, teachers are less effective in supporting and connecting with racialized students in de-streamed classrooms. The study was conducted in the context of Ontario’s de-streaming initiatives, proposed increases to class sizes, changes to pedagogical delivery modes due to the covid-19 pandemic, and Canada’s rapidly developing anti-racism policies in education.