This paper presents part of a research study on the affordances of digital technologies in the learning of students with Autism Spectrum Disorders (ASD) undertaken in the Faculty of Education, University of Wollongong. The study is framed around the understanding of modern digital technologies, and Interactive Whiteboards (IWBs) in particular, as cognitive tools for teaching and learning based on the theory of social and cultural mediation of children’s development and learning (Vygotsky, 1978; Engestrom, 2001). The view of the IWB as a teaching and learning tool is twofold: firstly, the IWB is analysed as a tool that can be used to enhance teachers’ pedagogical practices (within the teacher’s activity); and secondly, the IWBs are analysed as a tool which allows the teacher to meet specific needs of the students with ASD. This paper presents a pilot study into the use of IWBs in the day-to-day teaching of seven children with ASD (12-13 years of age), since the technology was introduced to the educational setting. The methods of data gathering included a series of classroom observations, audio recordings, collection of artefacts and semi-structured interviews with teachers and administration. Activity Theory (Engestrom, 2001) is used to explore the integration of IWBs in the classroom environment where the individual, classroom and whole school contexts are considered. The consideration of multi-layered contexts of IWB implementation allowed us to examine factors such as teacher’s pedagogy, teacher-student and peer interactions, the setting’s ICT policies, and teacher professional development and collaboration.