James begins the chapter in a dreamlike conversation with a figure named Cunégonde, who challenges his hope of finding his family. Cunégonde tells James that hope is not a plan and explains slavery as a financial system in which enslaved people are treated as bank assets, not simply laborers. When James says the war might change his condition, Cunégonde warns that even if slavery ends, real freedom may still remain out of reach.

James wakes in Katie and Cotton's shack when Katie urgently tells him to hide because the overseer is coming. James conceals himself behind a barrel while Katie erases his tracks. Overseer Hopkins enters, ignores Katie's attempt to deflect him, and sexually assaults her. James imagines killing Hopkins, but he stays hidden because he knows that if he acts or is discovered, the white authorities would punish not only him but the entire enslaved community, and the violence against Katie would continue anyway.

After Hopkins leaves, James comes out and sits silently with Katie. He realizes that any apology would be hollow beside the reality they both already understand. Instead of turning away from what happened, James forces himself to feel his rage fully, deciding to learn how anger might be used rather than merely suffered.

When Cotton returns, James and Cotton share a look that suggests Cotton understands something has happened. James leaves without staying for their exchange because he recognizes that his presence has made Katie and Cotton more vulnerable. Outside, as dusk comes on, James decides the safest place is the cave on Jackson Island, where he can survive alone and wait for Huck to bring news about Sadie and Lizzie.

James tells no one of his plan, partly to protect others and partly because he no longer trusts everyone in the quarters. He swims the channel at dusk, sleeps on the beach rather than risk traveling through the brush at night, and at first light steals a catfish from a trotline. After navigating the woods, avoiding a cottonmouth, and struggling to start a fire after losing his glass, James reaches the cave, cooks the fish, and settles in to wait, comforted that his pencil has survived.