The rate of competitive employment, or employment in community settings for minimum wage or higher, of working-age individuals with disabilities trails behind individuals without disabilities in the United States. These statistics are even more alarming among Hispanic individuals who have disabilities. The purpose of this study was to explore the negative and positive experiences of Hispanic caregivers from a Midwestern state as they support their family members with disabilities to achieve positive postschool outcomes, including competitive employment. We conducted semistructured interviews with 13 caregivers of family members with disabilities aged 14–25 years. Three key themes emerged from our analysis: (a) negative experiences with school educators, (b) negative experiences with community-based service providers, and (c) positive experiences and strategies for overcoming barriers. Implications for practice and future research are discussed.