One of the ways California is addressing issues of mass incarceration and prison over- crowding in the state is through recent reinvestment in education for justice involved students. Using sustainable development (Bruntland and Khalid, 1987) as a guiding framework, this dissertation examines California’s Corrections to Education pipeline. In particular, I explore the potential of the state’s community college system—the largest in the nation with 116 campuses—to help reduce recidivism by being a critical component in a formerly incarcerated student’s reintegration journey. I report on the results of a content analysis I conducted on what programs are available across all 116 campuses, in order to understand how many programs exist, where they exist, and what they look like along the program development spectrum. Informed by the results from the content analysis, I present a portraiture study of a southern California community college to tell the story of how this particular community has been serving these vulnerable students, some of the challenges formerly incarcerated students face, as well as the impact of the COVID-19 pandemic. The need for sustainable program development, policy implications, and future directions for research are discussed.