Although public support for unions has never been higher in the past 40 years, the opportunity to expand young people’s union membership rates and stop the decline of union participation remains a high priority for the American labor movement. In this report, we conducted exploratory research to better understand unions’ approaches to training young people and the experiences of young people (ages 16 to 24) learning a trade in registered apprenticeships. We interviewed three union organizations in three industries to learn how they prepare the next generation of workers and how young union apprentices are faring in their apprenticeships. Each program was selected based on their focus on training young people and to demonstrate union-based apprenticeship across different industries. There are several key lessons from the case studies that suggest how unions and other key partners can increase their recruitment of young people and assure their success: expand youth apprenticeships to sectors beyond construction; provide greater support for pre-apprenticeship and apprenticeship readiness programs; modernize their recruitment strategies; build partnerships within the education community; and pursue solutions to the perceived barriers of liability insurance and federal Hazardous Occupations Orders.