Dramatic changes in the labor market in the United States over the past 50 years have raised tremendous concern that many of the nation's youth are unprepared for the labor force. Policymakers and youth advocates are looking for strategies to improve the education system so that fewer youth drop out of high school and more have the skills and knowledge they need to contribute to the global economy. Initiatives such as Ready by 21 at the Forum for Youth Investment and the Mott Foundation's New Day for Learning highlight the importance of bringing together schools, workforce development programs, and out-of-school time (OST) programs to support youth to be successful in young adulthood. This article draws from several disciplines to integrate what is and is not known about engaging youth in career programming during OST. The authors begin by describing the challenges youth face as they transition into the labor market and the difficulties facing schools and higher education. They then juxtapose research on the potential for OST programs to support career development against evaluation research showing the challenges of changing long-term labor market outcomes. Next, they take a program-level approach to understanding OST career programming. They draw from their own study of 30 OST programs serving primarily low-income middle and high school youth to show the ways OST programs are currently supporting career development. They discuss some of the challenges of career programming and highlight how programs are overcoming these challenges. Their concluding discussion draws both from their own study and from the literature on education, workforce development, and OST programming to show how several OST programs are using scaffolding, in which youth move from lower-level experiences to more challenging ones, to keep youth engaged and progressing. (Contains 1 figure.)