In this critical autoethnography, I reflect on my experience teaching in a KIPP charter school in an urban, racially diverse city in the southwestern U.S. Over the past few decades KIPP has gained both prestige and resentment as a major character in the charter school movement. Their focus on supporting students from underrepresented racial backgrounds in achieving academic success has gained them ample support in many communities. How-ever, in this article I draw attention to the KIPP policies and practices that work directly against the organization's aims and instead support a process of acculturation. I engage with storytelling to bring the reader into my classroom experiences so that we might col-lectively trouble these disconnections and (re)consider how policies may impact students of Color in similar institutions.