High-quality out-of-school-time (OST) programs have a positive effect on youth development, but many cities have found it difficult to address the challenges of expanding and improving the quality of programs offered to underserved and high-need students. In response, The Wallace Foundation sponsored an initiative to help five cities increase collaboration, access, quality, information sharing, and sustainability in their OST systems. The overall goals of the initiative were to increase access, improve quality, develop information systems for decisionmaking, and plan for financial stability. Each city received a planning grant, which it focused on particular efforts tied to city context and area of need. The first in this three-volume series describes the cities' early work under the grant and analyzes the conditions and activities that contributed to their progress in building a coordinated system of services to meet the initiative's goals. Specifically, it addresses how city context affected the approaches implemented, the effectiveness of these approaches, and important enablers of progress, particularly in the areas of collaboration and coordination. Of particular note was the finding that city context and the involvement of the mayor had a significant influence on both decisionmaking and outcomes. In addition, the cities depended on the ability to gain buy-in from the schools and other key stakeholders, as well as financial assistance through city budgets and grants to ensure sustainability.