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In an effort to counter the harm that traditional schooling brings to Black students, we examined the way that two alternative pedagogical models–Montessori and Freedom School–can function together to provide culturally responsive educational experiences. As we examined the compatibility between Montessori and Freedom School, we found tensions that emerged between the pedagogies. Time, environment, and expertise served as barriers to the implementation of Montessori in the Freedom School setting, while student engagement ultimately dictated the success of merging these two models. To merge Montessori and Freedom School in a way that fully validates and embraces Black children, may be necessary to reconcile some Montessori ideals in order to make room for culturally sustaining pedagogies.