This qualitative research study explores the experiences of post-secondary students with Learning Disabilities (LDs). Using phenomenology, semi-structured interviews were conducted with four university students from Southern Ontario. The study discusses the strengths, challenges, commonalities and differences between the students‘ academic experiences through which they have derived current academic success. Data analysis draws from Critical Theory of Education, Social Model of Disability and Goffman‘s analysis of Stigma. The findings in this study provide insight into the classroom experiences of the students with LDs in elementary, middle and high schools. Further, they help understand ways adapted by students to navigate the education system through each of their varied experiences. This paper will conclude with implications and suggestions for social work professionals working with students who have LDs.