Youth apprenticeship has emerged as a potential strategy to recruit and train a new generation of early childhood educators. Many in the field hope it will help address teacher shortages, promote the recruitment and retention of diverse candidates, and provide the training and experience needed both to enter the profession and grow into higher-wage management and leadership roles. Beyond merely exposing students to the profession, youth apprenticeships are preparing them for full-time roles through structured, paid, work-based learning. But there are challenges to designing apprenticeships that provide equitable, high-quality learning opportunities for both the high school students and the young children with whom they would work. The following report takes a close look at how the youth apprenticeship pathway is working to support high school youth and meet the growing needs of the early educator workforce. Spotlighting a program in Oakland, California, it examines both lessons and possibilities. Oakland is attempting to solve its early childhood educator shortage by cultivating pipelines of well-prepared early educators that start in high school. Now, more than ever, the nation needs to test strategies like youth apprenticeship to find new ways to respond to teacher shortages and reopen child care to support economic recovery.