Because parents face barriers in advocating for their children within the special education system, some families request help from a special education advocate. In this study, we evaluated the perceptions of caregivers who requested advocacy support to understand why, for whom, when, and where the advocacy services were needed; how the advocate helped; and what the outcomes of the advocacy process were and which variables related to better outcomes. We conducted structured interviews with 36 families who had requested help and connected with an advocate over a 3-year period. Compared to national norms, families were more likely to request an advocate if their child had ASD, was in elementary school, and lived in non-rural areas. Family requests were most often for advocate attendance at IEP meetings; help to resolve disagreements with the school concerning supports and services; and information about school services and parental rights. Most advocate assistance was for a short duration, although a longer duration process, advocate attendance at meetings, and more intensive advocate assistance were all related to better outcomes. Most participants were satisfied with the advocate and with the end-result of the advocacy process. Findings are discussed in terms of implications for future research and practice.