The theology of Jesus’ experience of temptation involves the complexity of his divine and human natures, and the unique situation of living as one person in two natures (hypostatic union). When theologians consider the temptation of Jesus and the related questions about his impeccability, several presuppositions about the questions affect how to approach this particular paradox. The goal of this chapter is to pull back the curtain to see the relative involvement of each question with the others and the topic as a whole – Which Christology: Unitive or Disjunctive? Is God able to commit evil of is God impeccable? How much is God involved in human activity and moral freedom? What is freedom of will? What is temptation to sin? How is Jesus’ experience of temptation relevant for Christians in daily life? What was the role of the Holy Spirit in Jesus’ life and ministry? Could Jesus sin or not? How did Jesus avoid sin and fulfill all righteousness?