Students with learning disabilities continue to make advancements in their preparation for post-secondary studies and are one of the largest growing populations to enter colleges and universities. However, it is estimated that only forty percent of students with a learning disability report it to their post-secondary schools, creating difficulties for students to successfully transition to the new academic expectations. Research shows one significant reason for the lack of reporting is students' deficiency in their ability to self-advocate. The current study looks at seven high school students with identified learning disabilities, who receive special education services, to evaluate their understanding and use of self-advocacy skills in their high school setting, in their preparation for transition into post-secondary education. Through the use of the Constructivism-Interpretivism paradigm, with an inductive approach, this case study analysis produced five primary themes and ten associated sub-themes. Analysis of semi-structured interviews and artifacts reveal themes of Awareness, Security, Communication, Experiences, and Motivation. To understand how, from the perspective of the students, these themes emerged and what role they play in the students' understanding, development, and use of self-advocacy, two research questions guide the analysis: (1) How do high school students with learning disabilities view the role of the school and educators in their development and use self-advocacy skills? and (2) How do high school students with learning disabilities understand the role of self-advocacy skills in their preparation for post-secondary studies?