In preparation for Radcliffe College, Helen enrolled in the Cambridge School for Young Ladies. This institution was also called the Gilman School. Helen faced many challenges in this new learning environment, though her determination helped her through the first year. When Helen's second year at the Gilman School began, she was "full of hope and determination to succeed." This hope and determination was soon challenged. Helen enrolled in several challenging courses, and many of the "books [she] needed had not been embossed in time for [her] to begin with the classes." This made studying difficult. Her teachers could not give her individual help because many pupils were enrolled in each class. These challenges made it necessary for Miss Sullivan "to read all the books to" Helen using the manual alphabet. The teacher also had to "interpret for the instructors, and for the first time in eleven years it seemed as if her dear hand would not be equal to the task."
Eventually, conditions at school improved for Helen. Despite this, Mr. Gilman, the principal, thought that Helen's workload was too much and had it reduced. Helen wanted to complete her studies at the school in two more years, while Mr. Gilman wished her to stay "three years longer." Helen became unwell and could not attend class. Mr. Gilman made the decision to further reduce her workload. This made it impossible for Helen to complete her studies on time. It was because of this disagreement that Helen was withdrawn from the school by her mother. Her sister, Mildred, was also withdrawn.
Helen pursued the remainder of her studies under a tutor. Mr. Keith tutored her in Latin, Greek, and mathematics. Helen continued her education at Radcliffe College.