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In the US, many young people leave secondary school without the academic preparation needed for postsecondary education and the knowledge and core skills required in the workplace. In this paper, the focus is on large cities where there are the largest concentrations of disadvantaged students, high dropout rates and low achievement levels. The paper identifies key systemic policy issues, change strategies and overall state and local policy directions required to address this crisis. The paper begins with a vision of high schools for the 21st century, listing the characteristics of effective learning environments for young people. The goal of a reformed system of high schools is to prepare students to succeed in postsecondary education without the need for remedial assistance. An action agenda for state and urban leaders is recommended in order to ‘transform’ rather than just reform the secondary education system.