In 1896, Helen began studying at the Cambridge School for Young Ladies in preparation for admittance into Radcliffe and was soon accompanied by her younger sister Mildred. But when Helen grew ill and could not attend classes one day during her second year, Mr. Gilman, the school's principal, argued that she was "breaking down" from the stress and insisted he change her schedule. Helen reports in Chapter XIX that the change in her schedule "would have rendered it impossible for [her] to take [her] final examinations with [her] class." When Miss Sullivan tried to battle Mr. Gilman on Helen's behalf but was unable to reach an agreement, Mrs. Keller, Helen's mother, had both Helen and Mildred withdrawn from the school. Instead, Helen continued her studies under a tutor of the Cambridge school by the name of Mr. Merton S. Keith.

Helen studied "algebra, geometry, Greek and Latin" under Mr. Keith twice a week while she was staying at Wrentham then five times a week once she was back in Boston. Miss Sullivan interpreted all of his instructions for Helen.

Helen describes her tutor as always having a very "gentle and forbearing," meaning tolerant, nature no matter how long it took her to grasp a subject of study. Though Helen found languages and literature easy subjects, she struggled to learn algebra and geometry; however, he was able to make mathematics interesting and patiently continued to help her, no matter how long it took her to grasp a concept. Helen was so grateful for his patience and teaching style that she notes her "stupidity would often have exhausted the patience of Job."

All in all, through her descriptions of Mr. Keith, we develop the understanding that he was a very well-educated, patient, kind, and level-headed man, whom she learned a great deal from, much more than she would have learned in the classroom.