The purpose of this study was to understand the personal experiences of students with learning disabilities who participated in a freshman academy and the perceptions of their parents. Through in-depth interviews of 28 students and parents, this phenomenological study sought to capture the insights, interpretations, and meanings the participants had of their experiences. Giving a voice to this under-represented population aids to further research within critical disability theory. The findings in this study suggest that participation in a freshman academy has the potential to positively affect students with learning disabilities in the social and academic domains. However, the schools attended by the students in this study lacked specific best practices recommended for both freshman academies and students with learning disabilities, which limited the success experienced by the students.