Situated in the larger questions of how to support the educational engagement and positive psychosocial development of young people with cancer, the purpose of this exploratory study was to address gaps in the literature and build understanding of how young people use digital and Internet-connected technologies in ways that support their social and academic engagement. Through a multiple case-design, I examined the school-based and everyday (outside of school) technology uses of five young people. This study found that the cancer experience changed or reframed a young person's motivational engagement with school. Doing well academically was a sign of a normalcy and an opportunity to gain control over some aspects of life amidst rapid change and uncertainty with one's health. Uses of digital and Internet-connected technologies afforded opportunities for young people to participate and have a felt academic presence in school without being physically present. The young people used different technologies in different ways depending on their learning preferences, the publicness of their experience, and/or their desire for personal privacy. Additionally, digital and Internet-connected technologies afforded young people and their families the opportunity to actively build community and construct and/or maintain identity across life spaces (e.g., home, hospital, school) in ways that fostered social support and social learning experiences. The everyday technology-uses of young people with cancer included the actions and practices of maintaining and managing existing relationships, building new supportive relationships, creating new roles and identities outside of their "sick role," and being there for others as a source of social support and learning. This study also found that technology uses challenged schools' instructional and policy assumptions about the meaning of being "in-class" or "present" for the purposes of learning and earning academic credit. Schools' uses of these technologies to support young people with cancer revealed classical or Cartesian epistemological underpinnings that were encoded in schools' curricula and pedagogies. To the extent that such underlying worldviews continue to guide schools' actions and practices, even when technologies are used to support young people with cancer, their full potential uses may not be realized. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]