Aims: Children with cancer may experience prolonged periods of hospitalization and school absence up to three years post-treatment. This isolation can have a detrimental impact on academic performance and psychosocial outcomes. As a response to the growing accessibility of interactive video-conferencing technologies and young people’s increasing familiarity with this mode of communication, a cohort of patients at Sydney Children’s Hospital trialed a program utilising video-conferencing (e.g.SkypeTM) to connect to their home school. Methods: Nineteen patients, parents and teachers participated in semi-structured interviews to evaluate the efficacy and feasibility of this program. The results were analyzed using the qualitative framework of Miles and Huberman. Results: The program was positively evaluated by all three groups of stakeholders. Seventy-nine percent of parents/ patients (n=11), reported that it provided them with a sense of normalcy and connection to the outside world often boosting patients’ mood. Whilst some patients indicated initial reluctance to participate, 86% of parents/teachers (n=12) reported that the program increased patient motivation and strengthened relationships with classmates and teachers. Teachers (n=5) highlighted the benefit of allowing classmates to see physical changes in the patient, and reported that this demystified the patient’s cancer experience and assisted with school re-integration. Younger students primarily benefited from the social interaction facilitated by the program, whilst older students also used it for educational purposes. Reported barriers included: financial costs, substantial time commitments, bureaucratic hurdles, technical difficulties, objections from the school community (e.g. privacy issues) and conflict between hospital/school timetables. Conclusions: Video-conferencing technologies may provide an important tool to connect childhood cancer patients to their classrooms by supporting their academic progress and acceptance by peers. We identified a number of barriers to the practical delivery of educational services for children isolated from school. Further investigation into technical and logistical challenges faced by this and similar programs is warranted.