The twins quickly become the most popular people in town. Judge Driscoll exercises his prerogative and is the first to take them driving, to show them off in public. He takes them to meet Pudd'nhead Wilson, with whom they become fast friends. Pudd'nhead has spent his day wondering about a strange thing he has seen: looking out his window at about dawn, he saw what appeared to be a young woman in "Tom"'s room in the judge's house. She seemed to be practicing artful feminine gestures. Pudd'nhead was not able to see her face. A few hours later Pudd'nhead paid a visit to Mrs. Pratt, by which he learned, without mentioning his sighting, that "Tom" was supposedly out of town and there were no newcomers to the house whose presence could account for the young woman he had seen.
While "Tom" has been away at Yale, Roxy has been working on steamboats as a chambermaid. She has been popular with the boats' crews, and has saved up a good deal of money. Shortly before the twins' appearance in Dawson's Landing, her arthritis becomes severe enough that she decides to retire and live off her savings. Disembarking in New Orleans, she finds that the bank in which her savings were deposited has failed, and her money is gone. Crushed, she decides to go back to Dawson's Landing, where she has friends. She also resolves to approach her biological son, "Tom," whom she hopes has been mellowed by time and maturity. She secretly hopes he will give her a small stipend. Her friends in Dawson's Landing, who are still slaves, take her in and feed her, and "Chambers" gives her an update on "Tom," who has been gambling heavily and has gotten in trouble with the judge because of his debts. Roxy is distressed for her own sake to hear that "Tom" has in fact been disinherited. "Chambers" gives her new hope, though, by telling her that a new will has been made, once again making "Tom" the heir to the judge's estate.
Roxy sends "Chambers" to request an audience for her with "Tom." "Tom" beats "Chambers," then agrees to see Roxy. When she asks him for a dollar he is furious. She is shocked by his cruelty and tells him that the next time she gives him a chance to do good for her he will fall down on his knees and beg to take it. Something in her expression scares "Tom," who figures she somehow knows about his recent activities. He offers her a dollar, but she tells him that he must beg her not to go to his uncle. She is, of course, referring to his true parentage, although he doesn't know this. She manages to scare him enough that, despite the indignity of kneeling before a black woman, he begs her not to ruin him and gives her five dollars. She tells him that she will let him in on the disastrous secret that threatens him if he'll come to the "haunted house" that night. Before she leaves she also demands a bottle of whiskey from him.
"Tom" does come to the "haunted house" that night, and Roxy tells him the story of his parentage. He threatens her, but she tells him that someone else, a man, has the information in writing, so killing her would do "Tom" no good (she is bluffing, not referring to Pudd'nhead's fingerprints). Roxy demands that "Tom" call her mother, which, after some difficulty, he does. She also demands that he turn over a part of his allowance to her. He tells her that he is deeply in debt, and that he has been breaking into houses to service the debt. Roxy approves of this action, and offers to help, but he refuses and asks her to leave town. She agrees, providing that he gives her money regularly. Then she breaks down, talking to him of the emotional trials he has put her through. "Tom" is confused and reminds her that he didn't know she was his mother. Then he asks her who his father is. She tells him that it was Colonel Cecil Burleigh Essex, another town leader of old Virginian stock.
The next morning "Tom" awakens after a night of dreams about his racial background. He is wondering why people were made "black" and "white," and why blacks are treated so badly, and why he has never wondered about these things before, when "Chambers" comes in to call him to breakfast. "Tom" is immediately ashamed that he, technically a black man, is being waited on by a white man. The next few days are difficult for "Tom," as he is forced to rethink his relations with everyone he knows. He finds himself acting the stereotypically submissive part of the black man. But after a week or so, he relapses into his old ways. He and Roxy meet occasionally, and have begun to forge a relationship, although each resents the other: she dominates him, while he admires her commanding presence. "Tom"'s gambling debts begin to mount up again, and he decides to undertake another round of robberies in the town. He breaks into houses only in Dawson's Landing because he would not chance breaking into a house thats layout was unfamiliar. He disguises himself as a girl, but then one day notices Pudd'nhead Wilson staring at him through his window. He switches into an old dress of Roxy's and robs the houses of those who have gone to see the twins on the day of their arrival at Aunt Patsy's. His raid is successful, and the only loose end is Pudd'nhead, who is still wondering about the girl he saw in "Tom"'s window.
Twain is famous for writing haphazardly, and this is a section where that shows. Roxy goes from being a hard worker to drinking and thieving, and Colonel Essex suddenly reappears after a brief and stilted mention in the first chapters. It is obvious that Twain had to try hard to make certain parts of the plot come together, and the lack of explanation and motivation in this section can be difficult to explain. Yet this is also a section of intricate design, as the arrival of the twins coincides with "Tom"'s most desperate moment. The reader has been tricked into thinking that it will be the twins who are the con-artists, while it is in reality the town's leading son, "Tom" Driscoll, who robs the townspeople blind. Again Twain complicates the situation, though, by making the twins unwitting accomplices to "Tom"'s crimes: the townspeople are robbed because they leave their homes and go to Aunt Patsy's to indulge their naïve fascination with exoticism and celebrity. Even the astute Pudd'nhead is not given enough information to see through appearances, although he at least realizes that there is some kind of problem.