Milligan is frustrated that the children have followed him, but he does not send them back. They see a Ten Man guarding the entrance to the docks, standing under a sign that says Risker Water Transport. The Ten Man is keeping a man prisoner in the boathouse. Kate suggests tranquilizing the Ten Man, but Milligan does not want to risk him falling into the water and drowning. Kate does not think that killing a Ten Man is a problem. Milligan makes the children promise to stay hidden and keep an eye on the boathouse. The children outwardly agree, but they privately make a plan of their own.

Milligan approaches the Ten Man. When both men disappear from sight, the children sneak into the boathouse. The prisoner, Risker, is at first distrustful, though he has been expecting them. Mr. Benedict paid for their passage to the duskwort island (he and Number Two are already there), but the Ten Man has sunk Risker’s boats. Reynie, wanting to know the location of the island, bribes Risker with the gift from Captain Noland—a diamond. Risker gives them the location and tells them that when they arrive, they must “follow the wind” (270), per Mr. Benedict’s instructions.