“Ban the box,” a policy that prohibits employers from asking upfront about criminal records, is often proffered as a remedy. However, this policy has had mixed results, unintended negative consequences and has not been tested through a full business cycle. Our own work suggests that the optimal solution relies on an employer who approaches second chance hiring with a conscious plan to support the needs associated with this demographic (e.g., a time or place to meet with a parole officer). Ban the box does little to drive this formula for success. Ultimately, second chance employers do get to the point where the “box” is an irrelevancy in the hiring process, but the key is establishing a route to that level of comfort.