Rates of chronic illness are increasing around the world and, accordingly, numbers of adolescent students living with chronic illness are also increasing. The challenges faced by these students and their teachers are complex. One of these challenges is the need of the adolescent with chronic illness to achieve some level of social conformity. Another major hurdle in the educational setting for adolescents living with chronic illness is dealing with the needs of others. Enduring the restrictions of illness is a challenge for all who live with chronic conditions, but is particularly demanding for adolescents in regard to their education. Appropriate and open communication is an area of particular concern for students with chronic illness. Within the challenges, there can also be opportunities for empowerment, through developing resilience. There must be more general understanding on the part of educators of the nature and impact of the various medical conditions which students living with chronic illness present. Communication is possibly the area of highest priority for teachers and schools to improve in relation to the education of students living with chronic illness. Closely linked with the issue of communication are the matters of managing school absence and the role of digital technologies. (Contains 1 note.)