Advocating for your child with a disability can be a daunting task for any parent. When the parent is also a school district employee, determining whether advocacy could impact one's position as an employee becomes inherently problematic. Using a heuristic case study approach, this inquiry's intent is to understand the experiences, barriers, and perceptions of job security related to advocating from inside the district as a parent-educator of a child with a learning disability. Three themes emerged that describe this parent-educator's experiences. Findings indicate this parent-educator encountered varied experiences. Specifically, these include experiences that were both positive and challenging in nature, barriers that were not anticipated by the parent-educator, and repercussions related to job security. Implications for practice and future research related to parents of children with disabilities who are also educators are discussed.