As volunteer advocates at the Community Empowerment Fund (CEF), a nonprofit that works with individuals toward goals of financial independence, we often work alongside justice-involved community members (those who have come into contact with any part of the criminal justice system) who routinely confront a society that continues to punish them long after they leave detention in the criminal-legal system. As they begin the slow work of rebuilding their lives and rejoining their respective communities, they must navigate limited housing options, employers who refuse to hire them, bureaucratic and nightmarish expungement processes and a public conditioned to fear and disregard them. One consistent barrier is the “Box”—a question on the initial employment application asking if the applicant has ever been convicted of a crime. Resulting in the disproportionate rejection of African-American and Latinx job applicants, this Box represents a prejudice ingrained in so many employers against the formerly incarcerated. It is a codification of denied opportunity to those seeking economic stability for themselves and their families. We witnessed countless individuals confront the disappointment, discouragement and rejection generated by the Box, and being forced to start over again. More often than not, we witnessed this rejection when CEF members applied to jobs at Duke University and its Health System.