School re-entry of children who have been absent from school due to severe illness is a complex process and requires effort and adjustment from the child and his parents, teachers, school systems, and classmates. To contribute to the understanding and accuracy of the school re-entry process of ill children, and to the development of re-entry programs in Israel, the present study examined the re-entry experience from the viewpoint of mothers and teachers. The study included 27 semi-structured interviews with mothers and teachers of children who re-entered school after a prolonged absence due to childhood cancer. The study findings suggest that changes in the child's self-perception, physical limitations brought on by the illness, as well as social difficulties, and altered academic abilities make it very difficult to re-enter school. School re-entry is more optimal when the sick child's relationship with the teacher and classmates is maintained during the absence, and when it is tailored and continuous learning support from the school. These findings emphasize the importance of maintaining an ongoing relationship during the ill child's absence from school and setting a clear re-entry plan by the school in accordance with the child and his parents.