Assistive technologies are essential enablers for individuals with visual impairments, but although Singapore is technologically advanced, students with visual impairments are not yet full participants in this technological society. This study investigates the barriers and challenges to the use of assistive technologies by students with visual impairments in Singapore in a special school context. Findings reveal limited content knowledge amongst teachers in assistive technology resulting in inconsistencies and inadequacies in the delivery of instruction. Students also display a mixed range of abilities ranging from little to basic knowledge. Where formal channels fail to impart knowledge, family and external influences are found to feature as potentially important contributors to skill acquisition in assistive technology and access. The evidence highlights an urgent need to equip teachers with training in assistive technology and to strengthen collaboration between school and stakeholders.