How do special education-related professionals parenting children with disabilities experience the special education system? This qualitative exploratory study delves into the experiences of 25 mother-educators who are special education-related professionals navigating the special education system for their children with disabilities. Through thematic analysis, our findings elucidate how the special education system perpetuates inequitable practices. The study describes four central themes: (1) the nuanced role of mother-educators' expertise, (2) the capacity and willingness of school staff to serve children with disabilities, (3) the inherent inequalities within the special education system, and (4) the role of advocacy. Most of these mother-educators could occasionally leverage social, cultural, and economic capital to advocate and secure services for their children. However, despite their ability to leverage such resources and extensive knowledge about their children and the special education system, these mother-educators encountered numerous challenges in advocating for and securing services for their children. We discuss the implications of our findings for federal mandates on family engagement and caution against the deficit-based nature of special education. Furthermore, we propose recommendations for fostering more equitable approaches within the system. This study underscores the need for systemic changes to ensure that all children with disabilities receive the support and services they deserve.