Community college professionals actively cultivate social justice within the U.S. system of higher education. We seek to meet the community wherever they and their skills are and provide the opportunities to take their knowledge and credentials to the next level. This can include offering incarcerated-based education. This work can be life changing for all involved in it, yet there is little literature providing guidance on this type of location-based programming. Therefore, within this article, we share our experiences partnering to offer short-term non-credit vocational certificate educational training programs in local jails to transform the students, families, college, and communities we serve.