For young people who have dropped out of school, are out of work, or lack connections to family or other caring adults, there are often no easy answers. Their hopes for a better life are frequently no different than those harbored by their more advantaged peers, but their path to adulthood is rendered more difficult by tangled combinations of skill deficits, impoverished neighborhoods, racial discrimination, family disintegration, and personal and behavioral challenges. As a result, strategies to help disconnected youth make successful transitions to adulthood typically are effective only when designed to address multiple needs--for continuing education, employment, mentoring, and a range of personal supports. This report describes how eight different cities have launched cross-system initiatives and what they have accomplished through these new collaborations. Their efforts vary greatly and involve a broad array of partners. Many initiatives began without clear long-term goals or fully developed blueprints for action. These early attempts to build relationships and trust, however, were crucial in setting the stage for future progress. The experience of all eight cities suggests that simply opening a dialogue about the gaps between public systems serving young people can yield major dividends, and that the benefits of collaboration become evident even when as few as two key agencies start working together. A list of resources is included.