Federal law states that any student suspected of having a disability must meet initial eligibility requirements in order to qualify for special education services. Moreover, an individual education program (IEP) team is required by federal law to re-evaluate each student with a disability, tri-annually, in order to assess his or her continued need for such services. The path toward initial eligibility is clearly outlined within federal legislation; however, the law does not explicate a path for declassification, or exiting, from special education services. Because of this, many students may remain labeled as a student with a disability when they may no longer require the specialized instruction or related services provided through special education. The purpose of this study, therefore, was to describe the experiences of high school special education leaders regarding declassification of students from receiving special education services. By conducting one-on-one, semi-structured interviews with seven special education leaders, the research questions helped to reveal their lived experiences as well as the processes and procedures they have utilized when discussing and determining declassification as an appropriate option for students served through special education. Additionally, the researcher’s field notes were used as a data source in order to add to the phenomenological value of the study. Respondents consistently noted specific instances of parental agreement or disagreement with the idea of declassification and additionally noted how those parental responses impacted their response to the situation, as a leader. As a result, the leaders’ reactions to a situation of declassification were shaped by the actions of the parents. Utilizing a phenomenological approach adds to the current body of literature by providing a unique lens for practitioners and policy makers to consider.