An abundance of research has shown that the practice of grade retention has many negative consequences for the lives of students who struggle academically. What is not readily apparent in the literature are the views of grade retention from adults who have experienced retention as youth. A total of 51 individuals (18 women, 33 men) enrolled in a post secondary institution participated in the study. The test group, those individuals who experienced grade retention, was comprised of 25 individuals, while the control group was comprised of 26 individuals. Participants were matched on age, gender, grade 12 grade point average (GPA), family structure, and family stressors. The retained group did not differ significantly from the control group on measures of self-esteem or self-efficacy. Additional analyses of the data resulted in significant correlations for the retained group, non-retained group, and the entire sample on self-esteem, subscales of the self-efficacy measure, and demographic questions. Implications and future directions are discussed.