Urban teacher residencies have emerged as an innovation for recruiting, preparing, and retaining teachers for high-need urban schools. Though residencies aim to prepare teachers for specific urban contexts, we know little about how context is conceptualized in the teacher education curriculum or what teachers learn about it. This study finds that participants in one residency in San Francisco came to see context as complex and layered, interrupting stigmas often associated with urban schools. Participants felt well prepared to teach in particular high-need settings, but their knowledge and skills did not necessarily transfer to other urban settings in the same city.