Parents have advocated for the educational rights of their children with disabilities for decades, and more so since the reauthorization of the Individuals With Disabilities Education Act (IDEA). Advocating for one’s child while working as an employee in the same school district where your child receives special education services comes with unforeseen complexities. Using a heuristic case study approach, this inquiry intended to discern the experiences, barriers, and perceptions of job security of two parent-educators with children with autism. Findings suggest unanticipated experiences and challenges within their dual, parent-educator role as indicated by the theory of responsible advocacy. Perceived employment consequences related to advocating from within the school system are also discussed along with implications for such parent-educators and their role in improving parent–school partnerships in special education.