At Sunday's military parade, Willie sees May Wynn in the crowd. She shouts, "I take it all back. You win," and Willie misses his commands and embarrasses himself in front of the entire commandment. Ensign Brain catches him and brings him to the authorities for reprimand. He is eventually handed over to Commander Morton. Morton remembers that Willies got a commendation for his essay on the frictionless bearing, and arranges a compromise. Instead of throwing Willie out of the Navy outright, Morton brings Willie's total to demerit count to forty- eight, two less than the number that requires automatic expulsion. He also confines Willie to the base for the extent of his apprenticeship.
That night, Willy writes a long letter to May, promising to see her as soon as he is free of the base. The next day, Willie's father makes a surprise visit. Willie explains his dilemma, and Mr. Keith reveals that Mrs. Keith has been arranging a more plush duty for him anyway. Willie asks his father to call off his mother. Willie and his father part warmly. Over the next few weeks, Willy avoids all demerits, and elevates himself to thirty-first in his class. May Wynn and Mrs. Keith visit from time to time, but the meetings are simply cordial and polite. The day comes for graduation and assignment of orders. Instead of asking for the assignment he wants, Willie writes in preferences he thinks would show off his devotion and bravery. Instead of the Annapolis communication school that he had been hoping for, Willie receives duty aboard the minesweeper/destroyer DMS Caine.
As the stories of Willie's training and his relationship with May Wynn develop, we begin to feel sympathetic toward Willie. Wouk draws an analogy between Willie's step through the door into military service and Alice's step through the looking glass into Wonderland. Willie enters a world where he stands out like a sore thumb, but his best qualities begin to emerge. The Navy tests Willie in ways that reveal his intelligence, integrity, and willpower. In the Navy, Willie must rely on himself, for he cannot rely on his money or education.
Willie's blossoming independence elicits different reactions from the people close to him. It creates tension with his mother, who tries to shelter Willie from reality. She supported him in his irresponsible decision to be a lounge piano player, never forcing Willie to fend for himself. Now, she strongly opposes Willie's Naval career. Behind his back, she attempts to orchestrate a way for Willie to avoid leaving the country by getting him a public relations job. Willie's father, on the other hand, seems to come to a new understanding with his son as Willie matures as an individual. Their conversations are honest and caring, and portray a deep bond between the two that Willie seems to be discovering for the first time. Willie continues to think that his relationship with May Wynn is only a passing one, but moments of true affection begin to emerge. In moments when Willie doesn't have time to think, he reveals a growing love May.
An important theme of The Caine Mutiny begins to surface during Willie's naval training: the conflict between Willie's intelligence and illogical military procedures and regulations. Willie's intelligence rebels against the military's illogical commands. He tells his father, "What I've studied seems to me like a lot of rubbish. The rules, the lingo, strike me as comical I used to think it was preferable to the Army, but I'm sure now they're both the same kind of foolishness." Odd details of military service pepper the novel. Willie is amused, for example, that the elevators are labelled "HOIST." For the most part, Willie's willpower overcomes the protests of his intellect, as evidenced by his mastery of the passage on the frictionless bearing, the existence of which is a physical impossibility. At the same time, the military provides Willie with a feeling of belonging and brotherhood that had been missing from his life. This feeling helps him smooth over offenses to his intellect. The novel is also loaded with images of wealth out of place, such as the diamond on Mrs. Keith's hand that raps on the rough door to military life, and Willie's Princeton clothes in the dingy nightclub. As Willie becomes a more solid part of the Navy, however, these images fade, indicating Willie's integration and feeling of belonging.