Jean Trounstine taught literature to women inmates and cofounded an award-winning alternative probation program that uses writing and literature to offer prisoners a second chance. Trounstine began teaching literature, writing, and drama at Framingham Women’s Prison through her work as professor of humanities at Middlesex Community College. She innovated a special drama class in which the inmates studied plays with her and produced them in the prison. When Trounstine’s job at the prison was eliminated due to federal budget cuts, she found other ways to work on issues related to prison and the arts, such as the alternative probation program Changing Lives Through Literature. The program earned the New England Board of Higher Education’s Award for Excellence and an Exemplary Education grant from the National Endowment for the Humanities. Trounstine’s 2001 book Shakespeare Behind Bars explores her experiences teaching in prison, and she has also written a book of poetry and edited a collection of women writing on marriage. In 2018, she was awarded the International Gramsci Prize for her work in literature and prison. As of 2024, she has written or co-written five books, including Boy With A Knife: The Story of Murder, Remorse, and A Prisoner's Fight for Justice (2016) and MotherLove, a collection of short stories (2024).  

Jean Trounstine was honored at the 2000 Women Who Dared event in Boston.