An article that explores the theology of Sabbath keeping, and the biblical arguments for when God wishes his laws to be violated. A theology of the Sabbath, if it is to serve God’s desire in Scripture, must focus on the why of Sabbath, not the when. It cannot rely on arguments from authority or the Law as a cheap excuse for not engaging in arguments regarding Christ’s emphasis on its utility. A review of Jesus’ teachings about the Sabbath, both canonical and apocryphal, reveals a surprising consistency and emphasis on the same paradox: the Law of God will not pass away, but it will indeed at times be broken out of faith, a faith that fulfills its original purposes.