The middle grades are a time of transitions for teenagers. Attending a new school, developing new friendships, meeting new teachers, and becoming more independent are all part of the middle school experience. This article is a case report of a school district's experience using interactive video-conferencing technology to educate and socialize a homebound middle grades student. The report includes a description of the video technology, its costs, and issues experienced in implementation; a discussion of the roles of the teachers, the tutor, the parents, and the student; an assessment of the benefits of the technology and considerations for the student; and a brief review of current technologies available to schools. For Nick, a 13-year-old seventh grader recovering from a bone marrow transplant, a normal middle grades experience seemed unattainable. Instead, it appeared Nick's first year of middle school would consist of a home tutor and minimal interaction with his peers. To foster Nick's academic and psychosocial development during that year, his parents, school administrators, teachers, and instructional technology staff created a learning environment to allow him to fulfill his academic requirements and maintain relationships with peers. (Contains 3 figures.)