Conducting longitudinal interaction design research within an institution that caters for young people with special educational needs (SEN) is a challenging but fascinating task. This paper aims to elucidate some of the key factors that have emerged from conducting such research with students and staff in Three Ways School in Bath, UK. The various institutions and people involved are detailed as well as the most salient points for consideration when undertaking studies in the SEN context. The points are then reflected upon drawing on concrete examples from the researchers’ own experiences. These experiences, both positive and negative, may be of use to other researchers and practitioners when conducting research studies in the SEN classroom context and other potentially sensitive contexts.