Catholic apologetics can sometimes give the impression that every objection has a simple answer. But recent controversies have forced Catholics to wrestle more seriously with teachings that, at least on the surface, appear difficult to reconcile with Scripture and the Church's established tradition. In this video, I examine two of the hardest examples. First, I consider whether Pope Francis's declaration that the death penalty is "inadmissible" can be reconciled with centuries of biblical and magisterial teaching that regarded it as morally permissible in certain circumstances. Then I examine the apparent conflict between the nineteenth-century papal condemnations of religious liberty and Vatican II's declaration that the human person possesses a right to religious freedom. These questions do not necessarily prove that the Church has reversed herself, but they do require careful distinctions, greater humility, and a willingness to admit when newer formulations are confusing, prudential, or potentially in need of reform.