Mass incarceration is a troubling trend that is inconsistent with Christian belief and practice, yet many Christians do not see ending mass incarceration as an urgent discipleship issue. This article explores how theological and ideological leanings shape the way Christians view prisoners and approach prison reform, creating unique blind spots for conservative and liberal Christians. Pursuing holistic liberation for prisoners will require addressing individual, community, and systemic change and healing the misguided bifurcation between prison ministries and social justice advocacy. Focusing on biblical themes of liberation, mercy, prophetic confrontation of injustice, and solidarity, churches and organizations can move their communities toward a restorative vision for creation rather than a punitive one. By incorporating transformative practices within our discipleship efforts we will be able to see Christians grow in greater awareness of mass incarceration and commitment to setting prisoners free in Jesus’ name.