At the age of twelve, Ernest is enrolled in a grammar school at Roughborough, located about fifty miles from Battersby. Dr. Skinner, the headmaster, has a general reputation as a man of genius by virtue of his undergraduate debating record, his biblical scholarship, and his record of turning out boys who distinguish themselves as university students. Ernest, however, is one of a minority of pupils at Roughborough who do not fall under the spell of this man and his reputation as a "God-fearing earnest Christian and a Liberal, if not a Radical, in politics." Dr. Skinner is, in fact, a carbon copy of Ernest's father in his handling of boys. In his account of an evening of chess with Dr. Skinner, Overton reveals the petty, boorish, and pretentious qualities of the man.
Although he dutifully writes to his parents as though he were happy at Roughborough, Ernest is unhappy during his first two years there. At least, however, he is free of his father's bullying, and Dr. Skinner only occasionally makes his menacing presence felt. Fortunately, Ernest's schoolmates are mostly free of the offensive behavior so often associated with English public schools of that period. Only Ernest's reluctance to participate in athletics incurs their displeasure, but Ernest's aversion to studying impresses them favorably. He drinks more beer than is good for a frail boy, and he takes up smoking. The monthly "merit money" he receives roughly indicates his social standing: "too much for him to rank among the downright bad boys, but too little to put him among the good ones.
The author's satirical skill is nowhere better illustrated than in the episode in which Overton spends an evening with Dr. Skinner. Like Ernest's grandfather and father, Dr. Skinner is a successful man in the eyes of the world, but to Butler, through the alias of Overton, Dr. Skinner is the prime example of the pompous pedant, a particularly dangerous species of life. Feigning temperance, he is a glutton; pretending to great learning, he is an unblushing plagiarist; bullish among cowed pupils, he uses his office of headmaster to satisfy an insatiable ego. Overton's anecdotes which depict Dr. Skinner's "light" supper and his misconstruing of the initials "A.M.D.G." (which are engraved on a Roman Catholic chapel) give substance to Overton's indictment of the man. As Ernest's biographer, Overton makes good his warning to schoolmasters everywhere not to abuse their charges, for any one of them may one day tell the world what manner of headmasters they were.
The interior monologues of Theobald and Christina on their return journey to Battersby, after enrolling Ernest at Roughborough, amplify kinds of satire begun earlier. Accusing Ernest of being ungrateful and selfish, Theobald immediately despairs of Ernest because of his unselfish sharing of pocket money with his friends. Left to her own thoughts, Christina alternately congratulates herself on the impression she has made on Mrs. Skinner and speculates on the glorious possibility for Ernest to cultivate the friendship of a future lord who might be attending Roughborough.
In commenting on his subject's early school years, Overton laments Ernest's bondage to a routine which deprives him of discovering his stronger and truer self. Surrounded by prigs from birth, Ernest cannot avoid taking on some of the characteristics of priggishness, a term used by Overton to indicate all that is wrong with pursuing life as a duty and not as a pleasure. Instead of learning Latin and Greek, Ernest could spend his time more profitably in "growing bone and muscle." In other words, Ernest has little or no opportunity at Roughborough to rid himself of his father's stultifying influence; instead, he is fated to live in ignorance of the world and of his best possible natural self. By presenting this opinion in a mixture of biblical and scientific language, Overton strongly reflects the author's own deeply held anti-academic attitudes.