As online K-12 education becomes more prevalent, there arises a need to examine caring as it is experienced in technology-mediated contexts. The first article in this dissertation examines the definition of the term "caring pedagogies" and synthesizes relevant research helpful to understanding its application in a variety of contexts, including the technology-mediated context. The literature review is organized in the following categories: understanding caring pedagogy (defining and measuring), developing caring characteristics in individuals, developing caring communities, and developing caring in unique contexts. This article concludes that more research related to care is necessary in contexts other than the early childhood education context. The technology-mediated context would greatly benefit from such research. The second article in this dissertation investigates the experience of two teachers and four students in the Open High School of Utah and how they engaged in technology-mediated caring. Findings indicated that teachers care for students in this context by gaining a deep understanding of the student through shared perspective, continuous dialogue, and vigilant observation. Based on this understanding, teachers execute caring actions with the purpose of structuring the learning environment, attending to students' individual academic needs, and attending to students' well-being. Students completed the caring relationship by reacting to teachers' caring actions and acknowledging the care they received. The third article in this dissertation investigates technology choices conducive to creating and nurturing caring relationships in technology-mediated contexts. This article is based on the experience of the two teachers and four students in the Open High School of Utah. This study provides guidelines to help educators make technology choices that are effective in knowing the student, executing acts in the student's best interest, and receiving student reactions. Although research related to information and communication technologies has produced various useful frameworks for online education related to presence and immediacy, investigating technology-mediated caring has the potential to greatly enrich this scholarly discourse.