Pastorella remains trapped for a while in the dark den of the brigands. The captain of the brigands notices Pastorella among the prisoners and is captivated by her beauty. Nothing he says or does seems to win her favor, but at last Pastorella realizes that it might be a good idea to pretend to favor the captain. She pretends to like him, then pretends to be sick whenever he goes too far.
Without Sir Calidore to protect her, Pastorella is in a desperate situation, and she uses her wits the best she can in order to try to hold on until someone can come to rescue her. Because she’s protecting her chastity, her trickery is morally justified in the poem and even admirable.
One day while Pastorella is faking an illness, some merchants come to the brigands’ den hoping to buy all the shepherds as slaves. The captain doesn’t like this, but he brings all the shepherds out, including Pastorella, Melibee, and Coridon. The merchants are particularly interested in Pastorella, which angers the captain further, and he tries to claim that she is his. But the merchants say they’ll only make a deal if Pastorella is included.
Pastorella inspires greed on both sides of the deal. The new merchants lust after Pastorella, but the captain of the brigands is so full of lust himself that no amount of money will make the deal worthwhile if he loses her.
Things between the captain and the merchants get heated, until suddenly negotiations break down and they start to fight. Fearing the shepherds will rebel, the brigands kill some of them, including Melibee, although Coridon manages to sneak away. The captain fights for Pastorella with his life, and when he is mortally wounded, Pastorella falls down with him, looking dead. Though she has herself been seriously injured, when the victorious remaining brigands clear out the corpses, they find she’s still alive.
The brigands are violent men, and here they suffer the consequences of living such violent lifestyles, where a jealous argument can end in bloodshed. Innocents like Melibee get cut down in the chaos, although the brigand shows surprising (and perhaps misplaced) loyalty by giving up his life for Pastorella, suggesting that she is so fair that she can inspire good deeds even in bad people.
Meanwhile, Calidore is just coming back from the woods to see the devastation that the brigands inflicted on the shepherds’ home. He is furious and searches around until finally he finds Coridon (right after he managed to elude the brigands). Calidore asks Coridon about Pastorella, and he says he saw her fall down dead (which isn’t true, but which is how it looked from his perspective). This greatly upsets Calidore. Coridon tells of Melibee’s death as well and about the captain who tried to prevent Pastorella from dying.
Sir Calidore learns for himself how fragile the beautiful pastoral life can be. Seeing the death and destruction caused by the brigands, he begins to remember why he was a knight in the first place. This tragedy marks the beginning of Calidore’s transition back to accepting the responsibilities of knighthood.
Full of anguish, Calidore makes plans with Coridon to go directly to the den of the brigands and seek revenge. They disguise themselves as shepherds and travel until they reach a hill where they see some of the sheep that the thieves stole. The sheep are being tended by unfamiliar shepherds, who are asleep. Calidore wakes the shepherds and finds that they are poor grooms who have run away from their masters and been hired by the brigands.
Although Sir Calidore and Coridon were once rivals, tragedy has brought them together and taught them how to cooperate. Coridon seemed at times both cowardly and incompetent compared to Calidore, but the danger to his home forces him to grow and become braver like Calidore.
Calidore and Coridon then sneak into the den of the brigands, and Calidore is overjoyed to see that Pastorella is actually alive, although there are no other survivors. He breaks in and kills a brigand guard who puts up little resistance, then he calls to Pastorella. She goes to him, and they kiss and embrace. More guards come, but Calidore slays them like a lion among deer. He and Pastorella escape, recovering some of what the brigands stole from the shepherds.
The lack of survivors illustrates the consequences of greed, not just for innocent victims like the shepherds but for attackers like brigands as well. Calidore helps finish off the brigands and restore what he can of the shepherds’ possessions, but this adventure marks the end of his pastoral time.