Ensign Carmody takes Willie and Harding on a tour of the ship. For three hours, the ensigns explore every nook and cranny of the ship. Their final task is to climb the mast to the crow's nest. Once inside the nest, Harding says that he has to throw up. Willie offers his hat as a receptacle for the vomit. After dinner, there is some discussion about the terrible conditions in the clip shack, but the other officers do not want extra bunks in their quarters. Willie says that the bad conditions don't matter, which earns him an approving glance from Captain De Vriess. Willie and Harding begin their officer's qualification courses under Lieutenant Adams, an aristocratic regular officer. Their first assignment is create port and starboard diagrams of the ship by recalling what they saw on the tour. Desperate for sleep, Harding suggests that in the morning they copy a diagram from the ship's operating manuals. They head off to the clip shack, but find it filled with thick black smoke. After tossing and turning for a few hours, Willie leaves the shack and goes to sleep on a couch in the officer's wardroom.
Willie is woken up by a call to the four-to-eight watch. Willie attempts to run the watch as he was taught in officer's school, but the crew is not used to his stringency. They slack off, and Willie has to repeatedly scold an enlisted man named McKenzie for falling asleep on duty. Willie is shocked later by the crew's slow response the call of reveille. At breakfast, Keefer asks for help with decoding. Willie begins to help, but soon falls asleep. The captain comes and says that Willie should have had enough sleep from his Pearl Harbor duty to last a month.
Later that day, Willie is awakened to hear that Roland Keefer and two beautiful nurses came to visit him. De Vriess makes Willie finish his sketches of the ship before letting him leave. Willie angrily does the drawings while the captain entertains the girls next door. Willie finally leaves with his friends. He is in a terrible mood and drinks more than he ever has before. Early the next morning, a messenger wakes him with word of an urgent action-item that needs decoding. Willie is delighted to see that the message indicates that Captain De Vriess is to replaced by Lieutenant Commander Philip F. Queeg.
After four days of repairs, the Caine gets orders to head to sea. The mission is a simple minesweeping exercise, and the officers gripe about the insignificance of their role in the war. Keefer has been particularly disillusioned by his time on the Caine, and dreams of duty on aircraft carriers. He tells Willie that monkeys could do ninety-nine percent of Navy work, and the other one percent could be done by administrators in the States. Keefer says he is writing a novel about the war, which is set on an aircraft carrier. Willie later learns that Keefer's novel distracts him from his normal duties, which annoys the rest of the crew.
Captain De Vriess is forced to make a tricky maneuver to get out of the harbor, but he succeeds easily, and the Caine proceeds to its minesweeping exercise. They arrive at their rendezvous with the minesweeper DMS Moulton. Willie remembers that Keggs is stationed aboard the Moulton, and decides to flash him a greeting in Morse code. Willie is interrupted and harshly reprimanded by De Vriess for breaking his communication authority. De Vriess also reprimands the sailor of the watch for letting Willie to send the message. Willie stalks off, fuming that the captain picks on him and lets the rest of the crew misbehave.
At four o'clock, the minesweeping begins amid whirling bodies and profanity from the crew of the Caine. The gear is deployed in forty-five minutes, well below the Navy's recommended allowance of one hour. Still, Captain De Vriess criticizes the crew for falling short of his personal expectations for a thirty- minute launch. Willie first attributes the speed and precision of their launch to luck. His belief becomes awe as the Caine performs a complex series of minesweeping exercises. A radioman tells Willie that there is an urgent action item to be decoded. Willie shoves the communication in his pocket, and watches Maryk, who is performing a tricky maneuver. A wave sweeps over Willie and the communication, completely forgotten, dissolves to mush in the seawater.
Willie performs his duties with energy and resolve for the remainder of the four days of minesweeping exercises. Upon docking, Willie asks and receives permission to visit Keggs aboard the Moulton. Aboard the Moulton, Willie is shocked by the captain's treatment of the sailors. Keggs is constantly fearful, and scrambles to do not only his job, but also the job of the steward. The entire crew is confined to the ship for a week because they dropped a paravane.
Back on board the Caine, Willie gets an invitation to a dinner party given by Admiral Reynolds, whom Willie had impressed with his piano playing in Pearl Harbor. However, De Vriess has discovered the message that Willie lost. The message read that captain Queeg would be assuming command immediately. De Vriess punishes Willie by giving him an unsatisfactory fitness report and confining him to the ship for three days. Willie convinces the captain to allow him off the ship for the admiral's dinner. Willie decides to use his sway with the admiral to get off the Caine. On his way to the party, Willie gets the mail and finds the Bible from his father. It contains an inspiring note, which refers Willie to a passage in Ecclesiastes reading, "Whatsoever thy hand findeth to do, do it with thy might; for there is no work, nor device, nor knowledge, nor wisdom, in the grave, whither thou goest." The text is underlined with a note saying, "He's talking about your job on the Caine." Willie decides not to go to the party. The next morning, Captain Queeg reports to the ship.
In Willie's first few weeks aboard the Caine, a major conflict arises that will play a major part in the book's later events. This conflict is the tension that exists between the regular Navy men and the Navy men enlisted for the war effort. Before wartime, it was an honor to be accepted into officer school and gain an advanced post, but after war was declared, the guidelines and requirements were substantially relaxed because more officers were needed. Animosity sprung up between the regular sailors and the enlisted ones. The regulars felt that less competent, ill-prepared enlistees were being thrust upon them, and that the honor associated with their positions was being debased. As a result, the regulars segregated themselves from the enlisted men, as does Adams when he refuses to allow Willie and Harding to move their bunks into his cabin. This conflict also accounts for the notable distance Willie feels between himself and some of the other sailors, like Carmody, who is repeatedly referred to as an Annapolis man. Carmody is reluctant to talk frankly with Willie, and often appears uncomfortable in Willie's presence.
A conflict between appearance and function appears during the Caine's minesweeping exercises. Though by Navy standards, the Caine is rundown and mismanaged, it is the most effective minesweeper in the exercise group, substantially beating the recommended times for the launch and recovery of minesweeping equipment. Its hull is splotched with unfinished paint jobs, its deck is scatted with debris, and its crew attires itself as it pleases, but the ship accomplishes its mission with ease. Even the difficult maneuver that Captain De Vriess has to make in order to successfully exit port is passed off as routine and unworthy of comment. On the other hand, the Moulton, a model of Naval cleanliness and discipline, launches and recovers its gear in twice as much time as the Caine takes.
Willie's mounting displeasure aboard the Caine, especially with Captain De Vriess, eventually causes him to consider seeking a transfer through his connections with Admiral Reynolds in Pearl Harbor. He decides not to seek a transfer, however, when the Bible from his father arrives and Willie reads the passage Mr. Keith notes from Ecclesiastes. Willie takes the words to heart, and shows his growing maturity by deciding to stay with the Caine, see his duty out to the end, and do his best. In his civilian life, Willie never really finished any of the things he started. He never got the master's degree in comparative literature that would have guaranteed him a spot on a university staff, he never became a top billed lounge performer, always satisfied with the acts that got him by, and he never brought his relationship with May Wynn to any conclusion. Willie's desire to fulfill his military responsibilities, which include his duty to his country and to his father's last wishes, show a favorable change in his character. Willie's experiences in the military, the death of his father, and his own natural maturing process combine to make Willie act with resolve and perseverance aboard the Caine.
Willie comes to the Caine fresh out of officer's school, a spit and polish Navy man with no practical experience. After his shore time in Pearl Harbor and a few days on board, he becomes used to a relaxed military experience. He becomes conditioned to the Caine's familiarity among officers and its easygoing attitude toward the crew. When Willie visits Keggs aboard the Moulton, he sees the Navy's ideal ship and is appalled by it. The discipline that seemed ordinary just a month ago now strikes him as surprising and cruel.