Involvement with the criminal justice system is a serious detriment to a person’s chances of gaining employment, especially to those possessing both an ex-offender and minority status. As such, a large body of existing literature is dedicated to examining the policies and programs through which formerly incarcerated individuals can be more effectively integrated into the job market. One such method that has expanded since the late 1990s is the Ban the Box policy initiative, also known as the Fair Chance Act, which proposes that employers remove the conviction history question from job applications to ensure that applicants are first judged based on their individual qualifications while still permitting employers to examine applicants’ criminal histories at a later point in the hiring process. Research documenting the success of Ban the Box is mixed, however, and there is inconsistency among community members’ and scholars’ opinions on whether retaining Ban the Box is the right step towards facilitating employment for disadvantaged populations. Particularly concerning is the recent data demonstrating adverse consequences on the employment prospects of Black men with clean records in Ban the Box jurisdictions, a finding which some researchers attribute to the use of statistical discrimination by employers in the absence of applicants’ criminal history information. In light of this new data, the current study employs an in-depth interview method to ask individuals working in criminal justice capacities their opinions on the Ban the Box policy, the unintended consequences of the policy, the best way to approach reintegration efforts going forward with regard to Ban the Box. The participants involved in this study were ten staff members employed within various criminal justice organizations in southern California. Participants generally believed that Ban the Box helps formerly incarcerated job seekers overcome obstacles to employment, that the unintended consequences of the policy stem from preexisting systemic racial bias, and that reintegration efforts can best be realized by keeping Ban the Box in effect rather than repealing it.