In today's rapidly evolving educational environment, there is a pressing need to train teachers to respond to the increasingly diverse needs of students. Although physical education teacher education (PETE) programs across the country offer a wide variety of early field experiences for students, very few provide opportunities to work with currently incarcerated youths. One such partnership exists at Northern Illinois University (NIU), with a collaboration between the PETE program, the Illinois Department of Juvenile Justice, and Project FLEX. Project FLEX is a physical activity and life skills program for incarcerated youths, one of the only current programs in the United States. The program's primary aims are to incorporate life skill content into sport programming that fosters the transfer of these skills outside of programming and to engage youth in activities that increased physical activity levels while encouraging improvements to their sedentary lifestyle. The purpose of this article is to highlight the partnership between Project FLEX, the Illinois Department of Juvenile Justice, and the PETE program at NIU, discuss the partnership's impact on those involved, and share some potential future directions of the partnership. Further explanation of the interplay between the PETE program, the student's roles and responsibilities within Project FLEX, and how such early field experiences are currently situated within the PETE program will be discussed.