Christian has not traveled far into the Valley of Humiliation when he meets a foul Fiend. Christian has some armor supplied to him by the damsels of the Palace Beautiful but he has no covering on his back, so he cannot turn and run.

The monster, Apollyon, asks him where he has come from and where is going. Christian tells the fiend that he has come from the City of Destruction and is journeying to the City of Zion. Apollyon tells Christian that the City of Destruction is a country he rules. He demands to know why Christian has run away from his king. Christian replies that the life there was hard and the wages of sin were death.

Apollyon tells Christian that he will not let him go and that because he complains of the wages of death, he will gladly give him his “wages” now. Christian replies that he has given his faith to the Ruler of the City of Zion, but Apollyon points out that he already had been unfaithful to him many times already. He reminds Christian that he wandered willfully into the Slough of Despond, that he lost his Scroll as he slept, and that he tried to turn back at the sight of the lions at the Palace Beautiful.

Christian admits that all this is true, but the Ruler that he now serves is merciful. Apollyon attacks Christian, who uses such weapons as he has to defend himself. After a furious battle, Apollyon retreats.

Christian continues through the Valley of Humiliation until he comes to the Valley of the Shadow of Death. He meets two men who are fleeing from the Valley of Death. Christian says that despite the demons that the men encountered, this is the way he must go.

As he follows the narrow path, he sees a ditch on one side and a swamp on the other. Christian changes from his sword to the weapon “All Prayer.” He encounters more fiends and is tempted to turn back, but he presses on. He hears a voice telling him that although he walks in the Valley of the Shadow of Death, he must fear no evil for God is with him.

In the morning, Christian exits the Valley of Death. He encounters a cave with two giants, Pope and Pagan, but he realizes that Pagan has been dead for some time and Pope is too weakened to be much of a threat.