Educational research has established a link between zero tolerance disciplinary policies and increases in racial disproportionality in suspensions and expulsions of students of color. This article reports on a critical ethnography of Rivertown, a school district with urban characteristics, where we have been working with parents of color whose children are subjected to exclusionary discipline. Using the framework of Critical Race Theory in education, specifically Derrick Bell's interest-convergence principle, we argue that several interrelated barriers prevent movement toward racial equity: a culture of colorblindness and white fragility that silences race talk; contested definitions of the problem that obfuscate its racialized nature; and the persistence of a zero tolerance framework even with the implementation of a restorative justice pilot. We conclude by discussing our ongoing strategies for creating interest-convergence between White power-holders and communities of color in Rivertown.