Successful school transition is a basis for career development and eventual overall adult educational and socio-economic outcomes. Transitioning through primary school grades is a combination of relative academic and social skills acquired in each grade and forms the basis for subsequent academic and social success at ensuing educational pursuit and adult independent life. Evidence indicates that learners with autism spectrum disorder (ASD) and their families experience limiting challenges in their school transition at different levels. There is a gap in the literature as to the specific factors that constitute school transition difficulties in primary school learners with ASD in the area of study. The purpose of this study was to investigate challenges that learners with ASD face as they transition through school grades. The study adopted a phenomenological design with 12 participants (6 parents and 6 teachers). Two focus group discussions were held to collect data analysed using inductive thematic analysis. The results revealed three main themes, which included poor academic achievement and skills development, social and economic challenges as well as behavioural problems. The findings of the study suggest an increased need for home-school collaboration during the early stages and throughout the school years for the effective transition of learners with ASD. Thus, providing learners with ASD and their families with academic, emotional and behavioural intervention and support can help learners with autism to develop personal resources that will encourage their educational success.