Research on the role of institutions in influencing students' readiness for college has so far focused primarily on the school level and the state policy context, with only little attention to the district. This case study, based on interview data and documents collected over the course of a year, analyzes an urban district's attempt to create a systematic approach to improving the college readiness of its students, many of whom have been traditionally underserved by the educational system. It identifies factors contributing to progress as well as challenges encountered in several critical areas: (a) leadership commitment, (b) data infrastructure, (c) building adult capacity around data use and college readiness, (d) connecting indicators with supports to promote college readiness, and (e) partnerships with community and higher education institutions.