Progressive education is often examined through the lens of curricular theorists, educational historians, and the experience of practitioners. One perspective, infrequently found in the debate, has been the experiences of students educated under the progressive philosophy. The Southern author, Flannery O'Connor, who attended progressive schools on both the secondary and collegiate levels in Milledgeville, Georgia, is one such individual. The period that Flannery O'Connor attended progressive schools, from 1938 to 1945, can be considered the highpoint of the movement. This study will detail and examine three elements of the relationship between O'Connor and progressive education. First, a description of O'Connor's experiences during the seven years she was a student in two progressive educational institutions. Second, an exploration of her personal impressions and professional opinions of progressive education as found in O'Connor's correspondence and literary and artistic works. Third, an assessment and analysis of the influence progressive education may have had on O'Connor as an author.