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Intellectual disability is a developmental disorder that markedly affects cognitive and adaptive functioning. Learners with mild intellectual disability are capable of engaging in various occupations, including activities of daily living, leisure, social interactions, and employment. Employment is frequently regarded as a critical measure of successful outcomes following education. Nonetheless, individuals with mild intellectual disabilities often exit the educational system lacking the workforce readiness skills—such as communication, social skills, self-management, responsibility, problem-solving, decision-making, and job-specific competencies—essential for sustained employment in the open labour market. Low intelligence quotients restrict community engagement. The researcher noted that South Africa does not have adequate systems to facilitate the successful transition of these learners from school to the workplace. This research investigates the experiences of educators and occupational therapists to delineate concepts related to facilitating school-to-work transitions for learners with mild intellectual disabilities. A qualitative exploratory research design was utilised. Fifteen educators and eight occupational therapists from schools for learners with mild intellectual disabilities in the Gauteng province, Tshwane region, were selected through purposive sampling. Data were collected via five focus group discussions until saturation was achieved and analysed thematically. Five primary themes were identified: challenges associated with the Differentiated Curriculum and Assessment Policy Statement (DCAPS), accomplishments within the DCAPS framework, collaborative initiatives, resource deficiencies, and learnership placement. Educators and occupational therapists could support learners in specific domains; however, they encountered systemic challenges. This study generated significant data for policymakers, the Department of Education, occupational therapists, and vocational skills training educators in schools for Learners with Special Education Needs, aimed at facilitating a successful school-to-work transition for learners with mild intellectual disabilities.