This chapter recognizes the increasingly central role that distance technology plays in effective student, professional, and client education. It discusses key research findings related to caring in online teaching and learning settings. The chapter represents confirmation that Watson’s Human Caring Theory is relevant and applicable in digital settings. Effective integration of a theoretical framework into two vastly different settings such as digital and face to face is a hallmark of universality and elemental resonance. Human Caring Theory is fluidly applicable in both of these contexts because the basic tenets of Watson’s work resonate with the primal core of love from which caring intentionality originates before emerging into face-to-face, digital, or other domains of being. Watson’s work transcends time, space, and proximity, allowing it to serve as an effective framework for exploration and discovery now and into the future as new ways of interacting, connecting, loving, and caring unfolds.