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This phenomenological study investigates post-graduation outcomes of alumni from a two-year Comprehensive Transition Program (CTP) at a university in Southwest Florida, focusing on employment, independent living, and social engagement. While graduates reported increased autonomy in household tasks, transportation, and job competence, many continued to rely on family, benefits, and support networks—highlighting the centrality of interdependence rather than full independence. Employment rates were strong, with some individuals reporting career progression, while healthcare navigation and sustained social participation continued to emerge as ongoing challenges. Findings emphasize the need for transition programs to integrate healthcare self-advocacy, alumni support structures, and realistic pathways that reflect the complexity of adult life for individuals with intellectual disabilities.