The objective of this study was to describe how caring is experienced in the technology-mediated context of the Open High School in Utah, an online charter high school. Two female teachers, two male students, and two female students were interviewed three times over 9 months regarding their experience of caring teacher-student interactions. Data were analyzed using interpretative phenomenological analysis (IPA). Discovered themes were then organized into three superordinate themes: engrossment, motivational displacement, and reciprocity. Results suggest not only that caring interactions are possible in the online context, but also that specific caring pedagogies can strengthen the teacher-student relationship online. Additionally, evidence indicates that student reactions play an important role in caring in the online medium.