This paper is organized around three central questions: (1) What should be the primary goals of high school reform and what is the critical set of outcomes that matter for students? (2)Shat do we know about the strategies schools could use to pursue those goals? and (3) What are the implications of these strategies for the development of high school reform models and approaches and to what extent does test-based accountability impede or promote reform in these areas? The author begins by introducing the central policy problem--the gap between students' rising aspirations and their educational attainment. This paper then uses data from Chicago as a case study for focusing a discussion on what it will take to reduce dropout rates and increase postsecondary preparation and access for urban students. (Contains 3 tables, 12 figures, and 81 endnotes.)